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MICELLAR CATALYSIS
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DANIEL BLANKSCHTEIN
Department of Chemical
Engineering
Massachusetts Institute
of Technology
Cambridge, Massachusetts
S. KARABORNI
Shell International Petroleum
Company Limited
London, England
LISA B. QUENCER
The Dow Chemical Company
Midland, Michigan
JOHN F. SCAMEHORN
Institute for Applied Surfactant
Research
University of Oklahoma
Norman, Oklahoma
P. SOMASUNDARAN
Henry Krumb School of Mines
Columbia University
New York, New York
ERIC W. KALER
Department of Chemical
Engineering
University of Delaware
Newark, Delaware
CLARENCE MILLER
Department of Chemical
Engineering
Rice University
Houston, Texas
DON RUBINGH
The Procter & Gamble Company
Cincinnati, Ohio
BEREND SMIT
Shell International
Oil Products B.V.
Amsterdam, The Netherlands
JOHN TEXTER
Strider Research Corporation
Rochester, New York
SURFACTANT SCIENCE SERIES
FOUNDING EDITOR
MARTIN J. SCHICK
1918–1998
SERIES EDITOR
ARTHUR T. HUBBARD
Santa Barbara Science Project
Santa Barbara, California
ADVISORY BOARD
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1. Nonionic Surfactants, edited by Martin J. Schick(see also
Volumes 19, 23, and 60)
2. Solvent Properties of Surfactant Solutions,
edited by Kozo
Shinoda
(see Volume 55)
3. Surfactant Biodegradation,
R. D. Swisher(see Volume 18)
4. Cationic Surfactants,
edited by Eric Jungermann(see also
Volumes 34, 37, and 53)
5. Detergency: Theory and Test Methods (in three parts),
edited by
W. G. Cutler and R. C. Davis
(see also Volume 20)
6. Emulsions and Emulsion Technology (in three parts),
edited by
Kenneth J. Lissant
7. Anionic Surfactants (in two parts), edited by Warner M. Linfield
(see Volume 56)
8. Anionic Surfactants: Chemical Analysis,
edited by John Cross
9. Stabilization of Colloidal Dispersions by Polymer Adsorption,
Tatsuo Sato and Richard Ruch
10. Anionic Surfactants: Biochemistry, Toxicology, Dermatology,
edited by Christian Gloxhuber(see Volume 43)
11. Anionic Surfactants: Physical Chemistry of Surfactant Action,
edited by E. H. Lucassen-Reynders
12. Amphoteric Surfactants, edited by B. R. Bluestein
and Clifford L. Hilton
(see Volume 59)
13. Demulsification: Industrial Applications,
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14. Surfactants in Textile Processing, Arved Datyner
15. Electrical Phenomena at Interfaces: Fundamentals,
Measurements, and Applications,
edited by Ayao Kitahara
and Akira Watanabe
16. Surfactants in Cosmetics, edited by Martin M. Rieger (see
Volume 68)
17. Interfacial Phenomena: Equilibrium and Dynamic Effects,
Clarence A. Miller and P. Neogi
18. Surfactant Biodegradation: Second Edition, Revised
and Expanded,
R. D. Swisher
19. Nonionic Surfactants: Chemical Analysis, edited by John Cross
20. Detergency: Theory and Technology, edited by W. Gale Cutler
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21. Interfacial Phenomena in Apolar Media, edited by
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22. Surfactant Solutions: New Methods of Investigation, edited by
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23. Nonionic Surfactants: Physical Chemistry, edited by
Martin J. Schick
24. Microemulsion Systems, edited by Henri L. Rosano
and Marc Clausse
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25. Biosurfactants and Biotechnology, edited by Naim Kosaric,
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26. Surfactants in Emerging Technologies, edited by Milton J. Rosen
27. Reagents in Mineral Technology, edited by P. Somasundaran
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28. Surfactants in Chemical/Process Engineering, edited by
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36. Interfacial Phenomena in Petroleum Recovery, edited by
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39. Interfacial Phenomena in Biological Systems, edited by
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40. Analysis of Surfactants, Thomas M. Schmitt(see Volume 96)
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42. Polymeric Surfactants, Irja Piirma
43. Anionic Surfactants: Biochemistry, Toxicology, Dermatology.
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48. Biosurfactants: Production Properties Applications, edited by
Naim Kosaric
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50. Fluorinated Surfactants: Synthesis Properties Applications,
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52. Technological Applications of Dispersions, edited by
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55. Solubilization in Surfactant Aggregates, edited by
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56. Anionic Surfactants: Organic Chemistry, edited by
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61. Emulsions and Emulsion Stability, edited by Johan Sjöblom
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70. Structure-Performance Relationships in Surfactants, edited by
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71. Powdered Detergents, edited by Michael S. Showell
72. Nonionic Surfactants: Organic Chemistry, edited by
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73. Anionic Surfactants: Analytical Chemistry, Second Edition,
Revised and Expanded,
edited by John Cross
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74. Novel Surfactants: Preparation, Applications,
and Biodegradability,
edited by Krister Holmberg
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Measurements, and Applications, Second Edition, Revised
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edited by Hiroyuki Ohshima and Kunio Furusawa
77. Polymer-Surfactant Systems, edited by Jan C. T. Kwak
78. Surfaces of Nanoparticles and Porous Materials, edited by
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79. Surface Chemistry and Electrochemistry of Membranes,
edited by Torben Smith Sørensen
80. Interfacial Phenomena in Chromatography, edited by
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81. Solid–Liquid Dispersions, Bohuslav Dobiás, Xueping Qiu,
and Wolfgang von Rybinski
82. Handbook of Detergents, editor in chief: Uri ZollerPart A:
Properties,
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84. Dispersions: Characterization, Testing, and Measurement,
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85. Interfacial Forces and Fields: Theory and Applications, edited by
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86. Silicone Surfactants, edited by Randal M. Hill
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92. Fine Particles: Synthesis, Characterization, and Mechanisms
of Growth,
edited by Tadao Sugimoto
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Applications,
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96. Analysis of Surfactants: Second Edition, Revised and Expanded,
Thomas M. Schmitt
97. Fluorinated Surfactants and Repellents: Second Edition,
Revised and Expanded,
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98. Detergency of Specialty Surfactants, edited by Floyd E. Friedli
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99. Physical Chemistry of Polyelectrolytes, edited by
Tsetska Radeva
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101. Protein-Based Surfactants: Synthesis, Physicochemical
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107. Adsorption: Theory, Modeling, and Analysis, edited by
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108. Interfacial Applications in Environmental Engineering,edited by
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and Expanded,
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Second Edition, Revised and Expanded,
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and Minoru Ueno
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and Hans Joachim Schulze
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and Applications,
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120. Microporous Media: Synthesis, Properties, and Modeling,
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HirotsuguYasuda
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Analysis,
edited by Heinrich Waldhoff and Rüdiger Spilker
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and Expanded,
edited by Masahiko Abe and John F. Scamehorn
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Microemulsions, Vesicles and Lyotropic Phases,
edited by
Raoul Zana
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Hansjoachim Stechemesser and Bohulav Dobiás
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and Patrick T. Spicer
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Formulation,
edited by Michael S. Showell
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edited by Aleksandar M. Spasic and Jyh-Ping Hsu
131. Colloidal Silica: Fundamentals and Applications, edited by
Horacio E. Bergna and William O. Roberts
132. Emulsions and Emulsion Stability, Second Edition, edited by
Johan Sjöblom
133. Micellar Catalysis, Mohammad Niyaz Khan
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MICELLAR CATALYSIS
Mohammad Niyaz Khan
University of Malaysia
Kuala Lumpur, Malaysia

DK3291_C000.fm Page ix Friday, July 21, 2006 10:17 AM

CRC Press
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Library of Congress Cataloging-in-Publication Data
Khan, Mohammad Niyaz.
Micellar catalysis / Mohammad Niyaz Khan.
p. cm. -- (Surfactant science series ; 133)
Includes bibliographical references and index.
ISBN 1-57444-490-5 (alk. paper)
1. Catalysis. 2. Micelles. I. Title. II. Series: Surfactant science series ; v. 133.
QD505.K53 2006
541’.395--dc22 2006040127
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Preface
Catalysis has been known since the 14th century, but the mechanistic aspects of
catalytic processes at the molecular level are far from fully understood. It is
almost certain that Nature controls the fascinating selectivity and speciﬁcity of
all biochemical and nonbiochemical reactions through catalytic processes. Much
of the work on catalysis lies in the domain of homogeneous and heterogeneous
catalysis. Micellar-mediated reactions are characterized as catalytic processes
involving microheterogeneous catalysis. Kinetic studies, and hence mechanistic
studies, of micellar-mediated reactions at the molecular level started only in the
late 1950s. But the lack of understanding of the highly dynamic micellar structure
and polarity of the micromicellar reaction environment has resulted in the devel-
opment of many kinetic models for micellar-mediated reactions. Although the
applicability of these models is not sufﬁciently general, each has increased our
understanding of the highly dynamic structural features of micelles, as well as
the complex mechanistic aspects of their effects on reaction rates.
This book strongly reﬂects my own philosophy of science. Much of the
problem with learning science arises from a lack of appreciation of the funda-
mental conceptual aspects of science. For example, it is much easier to under-
stand, and consequently to appreciate, how — rather than why — a certain event
occurs in the scientiﬁc domain. Furthermore, every such event poses three basic
challenges to scientists: (1) to discover a new event to understand, and to com-
prehend (2) how and (3) why such an event occurs. The complexity, and conse-
quently the challenge to appreciation increases as we move in turn from the ﬁrst
to the second to the third challenge. In the scientiﬁc domain, concepts and theories
are advanced to rationalize experimental observations. But sometimes the prob-
lem is that the same experimental observations can be almost equally well ratio-
nalized in terms of different concepts and theories. These alternative concepts
and theories cannot be discredited entirely, because they help develop more
reﬁned and coherent concepts and theories. To the best of my ability, I have tried
to keep these ideas in mind while writing this book.
The physicochemical properties of a micelle, as well as the forces responsible
for its formation and highly dynamic structural features, are described in Chapter
1. Chemical forces or molecular interactions responsible for catalytic effects and
general mechanisms

⎯

also called general theories of catalytic processes — are
described in some detail in Chapter 2. General mechanisms or various kinetic
models for micelle-catalyzed reactions are discussed in Chapter 3, and Chapter
4 discusses the effects of micelles on the rate constants of unimolecular, sol-
volytic, bimolecular, and intramolecular organic reactions; the effects of mixed
aqueous-organic solvents on the micellar binding constants of solubilizates; and

DK3291_C000.fm Page xi Friday, July 21, 2006 10:17 AM

micelles as modiﬁers of reaction rates. The effects of mixed micelles on the rates
of unimolecular, solvolytic, and bimolecular reactions have been described in
Chapter 5. A rather brief description of the effects of metallomicelles and induced
metallomicelles on reaction rates is given in Chapter 6, and Chapter 7 discusses
the fundamental principles of kinetics and practical kinetics, which are often
needed in kinetic data analysis.
My debts to my postdoctoral supervisor, the late Professor Jack Hine of Ohio
State University, Columbus, are enormous. My research thinking has been highly
inﬂuenced by the work of a few individuals such as Professors J. Hine, M.L.
Bender, W.P. Jencks, T.C. Bruice, C.A. Bunton, A.J. Kirby, F.M. Menger, R.
Breslow, M.I. Page, and A. Williams. I would like to extend my sincere gratitude
to Professor Arthur Hubbard of the Santa Barbara Science Project, California,
who suggested that I write this book. I wish to express my sincere thanks to all
my coworkers, who directly and indirectly contributed to this work. I am also
grateful to Bayero University, Kano, Nigeria; National Science Council for R&D,
IRPA, Malaysia; Academy Sciences of Malaysia for Scientiﬁc Advancement
Grant Allocation (SAGA), and the University of Malaya for generous ﬁnancial
support of research in the area covered by this book. Last, but certainly not least,
I want to acknowledge my wife’s help at every step of the way.

Mohammad Niyaz Khan

Kuala Lumpur, Malaysia

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About the Author
Mohammad Niyaz Khan

is a professor at the Department of Chemistry, Uni-
versity of Malaya, Malaysia. After obtaining his Ph.D. in chemistry from Aligarh
Muslim University (1975), India, Dr. Niyaz carried out postdoctoral work with
Jack Hine at the Department of Chemistry (November 1975–December 1977)
and Louis Malspeis at the College of Pharmacy (January 1978–August 1980),
the Ohio State University, Columbus. He was on the faculty of science of Bayero
University, Kano, Nigeria, from late 1980 through late 1990 before joining the
chemistry department of University Putra Malaysia as a visiting research fellow.
Since late 1993, he has been a faculty member at the Department of Chemistry,
University of Malaya. He was a member of the Editorial Advisory Board of the

International Journal of Chemical Kinetics

(1996–1998), the

Indian Journal of
Chemistry

(1998), and

Malaysian Journal of Science

(2001–2004). His research
has centered around two areas: (1) kinetics and mechanisms of homogeneous
catalysis and intramolecular organic reactions, and (2) kinetics and mechanisms
of micellar catalysis of organic reactions.

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Contents
Chapter 1

Micelles............................................................................................1
1.1 Normal Micelles ..........................................................................................1
1.1.1 Critical Micelle Concentration (CMC) and Its
Determination ..................................................................................2
1.1.2 Effects of Additives on CMC..........................................................6
1.1.3 Thermodynamics of Micelle Formation .......................................15
1.1.4 Structure of Micelles .....................................................................23
1.1.4.1 Effects of Concentration of Micelle-Forming
Surfactant and Temperature ............................................24
1.1.4.2 The Random Micelle Aggregation Model for
Sphere-to-Rodlike Transition..........................................26
1.1.4.3 Effects of Additives.........................................................27
1.1.4.4 Effects of Speciﬁc Additives...........................................30
1.1.5 Micellar Location of the Solubilizate ...........................................33
1.1.6 Kinetics of Micellization and Micellar Solubilization..................35
1.1.6.1 Kinetics of Micellization ................................................36
1.1.6.2 Kinetics of Micellar Solubilization.................................41
1.1.6.3 Other Mechanisms of Intermicellar Exchange...............43
1.1.7 Water Penetration into Micellar Environment ..............................48
1.1.8 Internal Viscosity (Microviscosity) of Micelles ...........................51
1.2 Hemimicelles .............................................................................................54
1.3 Reversed Micelles......................................................................................58
References ...........................................................................................................63

Chapter 2

Catalysis in Chemical Reactions: General Theory
of Catalysis ....................................................................................89
2.1 Introduction................................................................................................89
2.1.1 Tautomerization of Ketones ..........................................................90
2.1.2 Hydrolysis of Esters ......................................................................91
2.1.3 Cleavage of Phthalamide under Mild Alkaline pH ......................92
2.1.4 Enzyme-Catalyzed Hydrolysis of Peptides (Amide Bonds).........94
2.2 Catalysis and Free-Energy Reaction Coordinate Diagram.......................95
2.2.1 Covalent Bonding Interaction .......................................................97
2.2.2 Electrovalent Bonding Interaction...............................................101
2.2.3 Resonance Interaction .................................................................102
2.2.4 Electrostatic Interaction...............................................................102
2.2.4.1 Ion–Ion Interaction........................................................103

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2.2.4.2 Ion–Dipole Interaction ..................................................103
2.2.4.3 Dipole–Dipole Interaction.............................................105
2.2.4.4 Hydrogen Bonding Interaction .....................................105
2.2.5 Hydrophobic Interaction..............................................................106
2.2.6 van der Waals Attractive and Repulsive (Steric)
Interactions ..................................................................................109
2.3 Mechanistic Change in Catalyzed Reactions..........................................112
2.4 Proximity and Shielding Effects of Catalyst...........................................114
2.5 Classiﬁcation of Catalysis .......................................................................115
2.5.1 Homogeneous Catalysis ..............................................................115
2.5.2 Heterogeneous Catalysis .............................................................116
2.5.3 Microheterogeneous (Micellar) Catalysis ...................................116
2.5.4 Nucleophilic Catalysis.................................................................117
2.5.4.1 Intermolecular Nucleophilic Catalysis..........................117
2.5.4.2 Rate Relationship between Intra- and
Intermolecular Reactions with Identical Reaction
Sites in Terms of Energetics .........................................122
2.5.4.3 Induced Intramolecular and Intramolecular
Induced Nucleophilic Catalysis ....................................125
2.5.5 Electrophilic Catalysis.................................................................134
2.5.5.1 Intermolecular Electrophilic Catalysis..........................136
2.5.5.2 Intramolecular Electrophilic Catalysis..........................144
2.5.6 Speciﬁc Base Catalysis ...............................................................149
2.5.7 Speciﬁc Acid Catalysis................................................................154
2.5.8 General Base Catalysis................................................................157
2.5.8.1 Intermolecular GB Catalysis.........................................158
2.5.8.2 Intramolecular General-Base-Assisted
Intermolecular Nucleophilic Reaction..........................166
2.5.9 General Acid Catalysis................................................................168
2.5.9.1 Intermolecular General Acid Catalysis.........................169
2.5.9.2 Simultaneous Occurrence of Both
Intermolecular General Acid and General
Base Catalysis ...............................................................171
2.5.9.3 Kinetic Ambiguity of the Assignment of
Intermolecular General Acid Catalysis.........................174
2.5.9.4 Intramolecular General-Acid-Assisted Intra- and
Intermolecular Nucleophilic Reactions ........................175
2.5.9.5 Simultaneous Occurrence of Intramolecular
General Acid and General Base Catalysis....................182
2.5.9.6 Induced Intramolecular GA–GB-Assisted
Cleavage of Substrate ...................................................183
2.5.10 Phase Transfer Catalysis .............................................................184
2.5.11 Asymmetric Catalysis..................................................................185
References .........................................................................................................186

DK3291_bookTOC.fm Page xvi Wednesday, July 19, 2006 1:55 PM

Chapter 3

General Mechanisms of Micellar Catalysis: Kinetic
Models for Micelle-Catalyzed Reactions....................................203
3.1 Introduction..............................................................................................203
3.2 Preequilibrium Kinetic Model of the Micelle.........................................204
3.3 Pseudophase Model of the Micelle.........................................................207
3.3.1 Cross-Interface Reaction between S
M

and R
W

............................209
3.3.2 Cross-Interface Reaction between S
W

and R
M

............................211
3.3.3 Cross-Interface Reaction: S
M

+ R
W

Parallel to S
M

+ R
M

............212
3.3.4 Cross-Interface Reaction: S
W

+ R
M

Parallel to S
M

+ R
M

............212
3.3.5 Cross-Interface Reactions: S
W

+ R
M

and S
M

+ R
W

Parallel
to S
M

+ R
M

...................................................................................213
3.3.6 Bimolecular Reactions That Do Not Involve Cross-Interface
Reactions......................................................................................215
3.3.7 The Pseudophase Ion-Exchange (PIE) Model............................217
3.3.8 Why the PIE Model Does Not Give a Better Data Fit
than the PP Model in a Reaction System with Plausible
Occurrence of an Ion-Exchange..................................................222
3.3.9 Mass-Action or Site-Binding Model...........................................224
3.3.10 Coulombic–Poisson–Boltzmann Spherical Cell Model..............224
3.3.11 An Empirical Kinetic Approach to Studying Ion Exchange
in Ionic Micellar-Mediated Reactions.........................................225
3.4 Berezin’s Pseudophase Model.................................................................242
3.5 The Multiple Micellar Pseudophase Model............................................244
3.6 Other Micellar Kinetic Models ...............................................................244
3.6.1 Piszkiewicz’s Kinetic Model.......................................................244
3.6.2 The Interfacial Kinetic Model.....................................................246
3.6.3 Extension of the PP Model .........................................................248
3.7 Dispersed Medium Model of Micellar Solution.....................................248
References .........................................................................................................251

Chapter 4

Normal Micelles: Effects on Reaction Rates..............................261
4.1 Introduction..............................................................................................261
4.2 Unimolecular and Solvolytic Reactions..................................................261
4.2.1 Micelles of Nonionic Nonfunctional Surfactants .......................263
4.2.2 Micelles of Ionic Nonfunctional Surfactants..............................270
4.3 Bimolecular Reactions.............................................................................284
4.3.1 Micelles of Nonionic Nonfunctional Surfactants .......................285
4.3.2 Micelles of Ionic Nonfunctional Surfactants..............................296
4.4 Intramolecular Reactions.........................................................................299
4.5 Effects of Mixed Aqueous–Organic Solvents on Micellar Binding
Constants (K
S

) of Solubilizates...............................................................303
4.6 Micelles as Modiﬁers of Reaction Rate..................................................305
References .........................................................................................................308

DK3291_bookTOC.fm Page xvii Wednesday, July 19, 2006 1:55 PM

Chapter 5

Mixed Normal Micelles: Effects on Reaction Rates ..................319
5.1 Introduction..............................................................................................319
5.2 Unimolecular and Solvolytic Reactions..................................................322
5.3 Bimolecular Reactions.............................................................................326
References .........................................................................................................335

Chapter 6

Metallomicelles: Effects on Reaction Rates ...............................343
6.1 Introduction..............................................................................................343
6.2 Nonfunctional Metallomicelles ...............................................................343
6.2.1 The TCK Model for Nonfunctional
Metallomicellar-Mediated Reactions ..........................................344
6.2.1.1 Effect of pH on k

′
NM

.....................................................348
6.2.2 Metallomicellar-Mediated Inorganic Reactions..........................353
6.3 Induced Functional Metallomicelles .......................................................354
References .........................................................................................................366

Chapter 7

Chemical Kinetics and Kinetic Parameters ................................371
7.1 Introduction..............................................................................................371
7.1.1 What Is a Chemical Reaction?....................................................371
7.1.1.1 One-Step or Elementary Chemical Reactions..............372
7.1.1.2 Multistep Chemical Reactions......................................372
7.1.1.3 Chemical Intermediate ..................................................372
7.1.2 Why Does a Chemical Reaction Occur? ....................................372
7.1.3 How Does a Chemical Reaction Occur? ....................................373
7.1.4 Why Do We Need to Know the Answers to These
Questions?....................................................................................373
7.1.5 What Is the Role of Chemical Kinetics in Answering These
Questions?....................................................................................374
7.2 Fundamentals of Chemical Kinetics .......................................................374
7.2.1 Rate of Chemical Reaction .........................................................374
7.2.2 Concept of Energy Barrier or the Energy of Activation.............375
7.2.3 Why Reactions with Moderately Stable Reactants
Involve Energy Barriers...............................................................376
7.2.4 Rate Law and Order of a Reaction.............................................377
7.2.5 Integrated Form of Rate Law......................................................377
7.2.6 Experimental Rate Law...............................................................378
7.2.7 Determination of the Experimental Rate Law............................379
7.2.7.1 One-Step First-Order Reactions....................................379
7.2.7.2 Irreversible First-Order Consecutive Reactions............392
7.3 Empirical Kinetic Equations ...................................................................397
7.3.1 Effects of Organic Cosolvent in Mixed Aqueous
Solution on the Reaction Rates...................................................399
7.3.2 Effects of [Salts] or [Additives] on the Reaction Rates .............400

DK3291_bookTOC.fm Page xviii Wednesday, July 19, 2006 1:55 PM

7.3.3 Effects of [Catalysts] and [Reactants] on the Reaction
Rates ............................................................................................400
7.3.3.1 Effects of [Micelles] on the Reaction Rates ................401
7.3.3.2 Effects of [Inert Salts] on k
obs

for Ionic
Micellar-Mediated Semiionic Reactions.......................401
7.3.3.3 Effects of the Concentration of
Nucleophiles/Catalysts on the Rate of Nucleophilic
Cleavage of Imides, Amides, and Esters......................405
7.4 Reaction Mechanism, Theoretical Rate Law, and Theoretical
Kinetic Equations ....................................................................................406
7.4.1 Mechanistic Implication of Equation 7.47..................................407
7.4.2 Mechanistic Implication of Equation 7.48..................................408
7.4.3 Mechanistic Implication of Equation 7.51..................................409
7.4.4 Mechanistic Implication of Equation 7.52..................................412
7.4.5 Mechanistic Implication of Equation 7.53..................................413
7.4.6 Mechanistic Implication of Equation 7.54..................................414
7.4.7 Mechanistic Implication of Equation 7.55..................................414
7.5 Reliability of Derived or Calculated Kinetic Parameters.......................416
7.5.1 Kinetic Equations Involving Primary Kinetic Data
(Y vs. X)......................................................................................416
7.5.2 Kinetic Equations Involving Secondary Kinetic Data
(Y vs. X)......................................................................................417
References .........................................................................................................423

Appendix A

......................................................................................................427

Appendix B

......................................................................................................433

Author Index

....................................................................................................439

Subject Index

...................................................................................................459

DK3291_bookTOC.fm Page xix Wednesday, July 19, 2006 1:55 PM

DK3291_bookTOC.fm Page xx Wednesday, July 19, 2006 1:55 PM

1

1
Micelles
1.1 NORMAL MICELLES
Almost all signiﬁcant or breakthrough scientiﬁc inventions were met with skep-
ticism from the world scientiﬁc community in the initial stages. This is natural,
for the human brain appears to be conditioned to deny any concept it ﬁrst encoun-
ters that is not supported by convincing and rational reasoning or proof. However,
this does not appear to be an absolute rule, because the human brain does accept,
knowingly or unknowingly, concepts based on mere intuition. A suggestion by
McBain regarding the formation of molecular aggregates in an aqueous solution
of surfactant at the turn of the 20th century was treated with incredulity by the
leading scientists of the time. McBain pointed out in a lecture to the Royal Society
of London that unusual solution properties of an aqueous solution of surfactant
above a critical surfactant concentration could be explained by surfactant aggre-
gation under such conditions.
1

A leading physical chemist chairing the meeting
responded to this idea with two words, “Nonsense, McBain.”
1

But, everyone today
who is familiar with colloidal chemistry accepts the notion that surfactant mole-
cules, above a critical surfactant concentration, do aggregate in aqueous solvents.
In 1936, Hartley
2

introduced the term

amphipathy

to describe the unusual prop-
erties of aqueous solutions of soap and detergent molecules:
This unsymmetrical duality of afﬁnity is so fundamental a property of parafﬁn-
chain ions, being directly responsible for all the major peculiarities of parafﬁn-chain
salts in aqueous solutions, that it is worthwhile, if only for emphasis, to give it a
special name. The property is essentially the simultaneous presence (in the same
molecule) of separately satisﬁable sympathy and antipathy for water. I propose,
therefore, to call this property

amphipathy

— the possession of both feelings.
A solute molecule is said to dissolve in water solvent when the absolute value
of

solvation energy

(i.e., energy released owing to formation of solvation shell
around the solute molecule) becomes equal to or larger than the energy required
to form a cavity in the water solvent for embedment of the solute molecule. A
surfactant (surface-active) or amphiphile molecule consists of both hydrophobic
(lipophilic or lipid-loving) and hydrophilic (lipophobic or lipid-hating) molecular
segments. When the hydrophobic segment becomes considerably larger than voids
in the three-dimensional structural network of water solvent, and the solvation
energy for a single molecule is not sufﬁcient to counterbalance the energy needed
to form a cavity for embedding the molecule, then surfactant molecules begin to

DK3291_book.fm Page 1 Wednesday, July 19, 2006 1:12 PM

2

Micellar Catalysis
aggregate, because it is energetically less expensive or easier to form a larger
cavity than a relatively smaller one. However, because the surfactant molecules
contain both hydrophilic segments (called

head groups

) and lipophilic segments
(generally long methylene chains [C
n

H
2n+1

with n > 8] called tails), packing of
head groups and tails during the formation of a micelle involves different ener-
getics in terms of molecular interactions. Thus, the shape and size of a micelle
depend upon the energetics of the interaction between adjacent hydrophilic head
groups as well as adjacent lipophilic tails. Surfactants are often classiﬁed on the
basis of an empirical scale called

hydrophilic–lipophilic balance

(HLB)

number

,
which gives a simple index for the molecular balance of surfactant at an oil–water
interface.
3

Based on characteristic physical properties of head groups, surfactants have
been categorized as cationic (if the head groups are cationic), anionic (if the head
groups are anionic), zwitterionic (if the head groups possess both cationic and
anionic sites), and nonionic (if the head groups are nonionic). The increase in
the concentration of a particular surfactant in an aqueous solvent reveals a sudden
change in various aqueous surfactant solution properties such as surface tension,
equivalent conductivity, solubilization, osmotic pressure, turbidity, self-diffusion,
magnetic resonance, UV-visible/ﬂuorescence spectra of solutes, and reaction rates
above a sharp surfactant concentration (Figure 1.1). Such changes in various
physical properties of an aqueous solution of the surfactant are attributed to the
formation of aggregates of surfactant molecules above a critical surfactant con-
centration, which is termed as

critical micelle concentration

(CMC), because
these surfactant molecular aggregates are called

micelles

. The word

micelle

,
which is now also called

normal micelle

, was introduced by McBain in 1913 to
describe the formation of molecular aggregates in aqueous solution of soaps.
4

The surfactant molecules below CMC are believed to remain as monomers.
However, the concept of surfactant molecules as monomers below CMC is con-
sidered to be an oversimpliﬁed situation.
5

A recent report provides ﬂuorescence
spectral evidence in favor of premicellar aggregates.
6

Although these micelles cannot be seen with naked eyes or detected directly
by UV-visible spectral studies (because the sizes of these micelles are signiﬁcantly
smaller than the wavelength of the electromagnetic radiation covering its UV-
visible region), there is convincing indirect experimental evidence, including
common logic and intuition, in favor of aggregates or micelles formation in
aqueous solutions of surfactants.
7

Aqueous solutions of micelle-forming surfac-
tants scatter light, and this property provided compelling evidence for the forma-
tion of surfactant aggregates or micelles.
8

1.1.1 C
RITICAL

M
ICELLE

C
ONCENTRATION

(CMC)
AND

I
TS

D
ETERMINATION

Critical micelle concentration

(CMC) of a surfactant is deﬁned as the optimum
aqueous concentration of the surfactant at which micelles begin to form under a
speciﬁc reaction condition. Extensive research on the physicochemical behavior

DK3291_book.fm Page 2 Wednesday, July 19, 2006 1:12 PM

Micelles

3
of aqueous organized molecular assemblies during the last few decades reveal
that CMC of a surfactant is an extremely important parameter in view of its
importance in determination and optimization of various characteristic properties
of micelles, such as micellar stability and binding afﬁnity/binding constant of a
solubilizate as well as surfactant use in facial cleansers, shampoo, and baby-care
products.
9,10

Various physicochemical properties of micellar solutions are dis-
tinctly different from those of nonmicellar solutions (aqueous solution containing
monomers) of the same surfactant, and this behavior of an aqueous solution of
a surfactant forms the basis for various physicochemical methods to determine
the value of CMC. These methods include the following:
1. Surface tension
2. Ionic conductance
3. Vapor pressure osmometry
4. Static light scattering
5. Dynamic light scattering
6. Refractive index
7. Dye solubilization
8. Dye micellization
9. Molecular adsorption
FIGURE 1.1

Change in physical properties of micellar aqueous solution as a function of
total surfactant concentration, [Surf]
T

. The point of intersection of two linear lines in each
plot represents the critical micelle concentration (CMC).
(Surf )
T
/ M
Physical properties ( , , , Δ,)
Δ

DK3291_book.fm Page 3 Wednesday, July 19, 2006 1:12 PM

4

Micellar Catalysis
10. Diffusion coefﬁcient
11. Viscosity
12. Partial molal volume
13. Sound velocity
The details of most of these methods are found in books
11

and review articles.
12

The structure of a micelle is highly dynamic as well as sensitive to additives;
because of these characteristic properties of micelles, the physicochemical meth-
ods produce slightly different CMCs of a surfactant.
8a,13,14

Although solubilization
of substances containing chromophores or ﬂuorescence for determination of CMC
has been criticized because incorporation of solubilizate into a micelle can change
the CMC values,
11c,15

the use of such a method is now common.
16

For instance,
because of the report
17

that the luminescent probe (pyrene) could be used to
determine the CMC of surfactant solutions, the so-called pyrene 1:3 ratio method
has become one of the most popular methods for the determination of CMC
18

in
pure
19

and mixed surfactant systems.
20–26

However, attempts have been made to
compare CMC values obtained from different physicochemical methods.
19,27–36

Apart from conventional techniques, a few more new techniques have recently
been introduced to determine CMC of a surfactant solution. For instance, Gosh
et al.
37

have determined CMC of surfactant solutions by the use of hyper-Rayleigh
scattering (HRS), which is sensitive to micellar size and shape changes. This
technique has also provided indirect evidence for the presence of premicellar
aggregates of much lower aggregation numbers compared to those of micelles.
The CMC value obtained by linear Rayleigh scattering is slightly higher than
that obtained by HRS, which is attributed to the known fact that CMC values do
vary a little depending upon the method employed for its determination. The
CMC values of anionic, cationic, and nonionic surfactants have been determined
by a new application of nuclear track microﬁlters,
38

and these CMC values have
been found to be comparable with the literature values. A spectrophotometric
estimation of CMC of ethoxylated alkyphenol surfactants has been shown to be
feasible through the so-called absorbance deviation method.
39

The CMC estimates
are satisfactory and, thus, the method may be an alternative for alkylphenol
nonionic surfactants. A new method of CMC determination has been reported,
which is based upon the decrease in the water structure in the critical range of
micelle formation.
40

The decrease in water structure is measured by the signiﬁcant
increase in the rate of disintegration of gelatin microcapsules.
Kinetic studies on micellar-catalyzed reactions form the backbone of this
book, and a quantitative analysis of kinetic data requires knowledge of the exact
value of CMC of the micellar solution under strict reaction conditions of kinetic
runs. However, most kinetic studies on micellar-catalyzed reactions have used
CMC values determined by the usual physical methods under experimental con-
ditions not strictly similar to those of kinetic runs. Although it is not impossible,
it is extremely difﬁcult from a practical point of view to obtain CMC values under
reaction kinetic conditions by using any of the various physicochemical methods.
Broxton et al.
41

have advanced a so-called kinetic graphical method to determine

DK3291_book.fm Page 4 Wednesday, July 19, 2006 1:12 PM

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Petersburg, aged 87.
1851. Tçm Jçhnsçn , a Norwegian, died at the Naval asylum,
Philadelphia, aged 100; the last survivor of the gallant crew who
fought with Paul Jones, in the desperate conflict with the Serapis in
1799.
1852. The sultan of Turkey issued a firman granting new rights and
privileges to his Christian subjects.

1854. The siege of Silistria raised; the Turks made a sortie, causing a
complete defeat of the Russians, forcing them to recross the Danube
in all haste, took several standards and a great quantity of baggage,
and killed or severely wounded five Russian generals.
1857. A riot took place in the city of New York, occasioned by a
dispute about the public offices, there having been two sets
appointed by different authorities. Mayor Wood was arrested for
assault and battery.
JUNE 17.
431 B. C. The dictator Tubeêtus Pçsthumus gained a victory over the
Æqui and Volsci, inconsiderable but noxious enemies of the
commonwealth.
1081. Rçbeêt Guiscaêd opened the famous siege of Durazzo, now in
European Turkey, on the gulf of Venice.
1272. An attempt made to assassinate Edward I of England in his
tent at Acre, by a messenger of the emir of Joppa. He received the
blow on his arm, grappled with the assassin, and throwing him on
the ground despatched him with his own dagger. The life of the
prince was saved by his wife, who sucked the poison from the
wound.
1458. Alfçnsç V, of Arragon (the magnanimous), died. He made
himself master of Naples and Sicily; aside from his exploits as a
warrior, he was a learned man and the patron of learning, and the
father of his people.
1614. William Bathe, an Irish Jesuit, died. He was rector of an Irish
school at Salamanca, and a writer on music and divinity.
1639. The king and his Scottish subjects met at Dunse, in Scotland,
and agreed that matters ecclesiastical should be decided by an
assembly, civil matters by parliament.

1658. Dunkirk surrendered to the French, and by them put into the
hands of the English.
1673. Father Maêquette, and Jçliet a citizen of Quebec, employed by
M. Talon for the discovery of the Mississippi, entered that noble river.
They descended to within three days' journey of the gulf of Mexico.
1685. The unfortunate duke of Argyle taken in a morass.
1696. Jçhn Sçbieski, king of Poland, died. He distinguished himself on
many occasions in the Polish wars but the greatest of his exploits
was the raising of the siege of Vienna, by which Europe was saved
from the calamities consequent upon an irruption of the Turks.
1719. Jçseéh Addisçn , editor of the Spectator, died. He was the
ornament of his age and country, and his writings will long continue
to be read and admired.
1734. Lçuis Hectçê Villaês, peer of France, died, aged 82. He early
adopted the profession of arms, and distinguished himself through a
long life as a brave and efficient officer.
1740. William Wyndham , an eminent English statesman, died. His
abilities led to his promotion to the highest offices in the state.
1745. Louisbourg, cape Breton, taken from the French by the British
and Massachusetts forces, under governor Shirley and admiral sir
Peter Warren.
1761. The first English "navigation canal" opened, extending from
Worsley to Manchester, 18 miles. It originated with Scroope, duke of
Bridgewater.
1775. Battle of Bunker's hill, and burning of Charlestown by the
British. The Americans were defeated with the loss of 453 killed,
wounded and missing. The killed, and those who died of their
wounds were 139, including general Warren. British loss, 1,054, of
whom 226 were killed, and among them colonel Abercromby and
major Pitcairn, who occasioned the first shedding of blood at
Lexington.

1776. British transports, George and Arabella, captured in Boston
bay by six American privateers. Among the prisoners taken was the
honorable Archibald Campbell, and 271 Highlanders.
1780. Bank opened in Philadelphia for supplying the army with
provisions, and £189,000 subscribed, payable in gold and silver.
1788. Convention at Poughkeepsie, N. Y., to consider the federal
constitution.
1789. The tiers etat, of France, were joined by the whole body of
inferior clergy with some nobles. They constituted themselves into a
legislative body, and took the name of national assembly.
1791. Selina, countess of Huntington, died. From habits of gaiety and
dissipation, she became suddenly grave and pious, and was
distinguished by very extensive charities.
1792. Battle of Zielime, in which the Polish army was defeated by a
superior force of Russians. The action lasted from 7 in the morning
till 5 in the evening. Loss of the Russians 4,000; that of the Poles
1,100.
1794. Ypres, in Belgium, surrendered to the French under Moreau.
Four battalions of Austrians, 6 of Hessians, 2 of Baden, 200 horse
chasseurs, 150 Austrian cannoniers, were taken prisoners, with 140
cannon.
1799. First day's battle of the Trebia, between the French under
Macdonald, and the Russians and Austrians under Suwarrow. The
French were compelled to fall back.
1807. Konigsberg, the capital of Prussia proper, taken by the French
under Soult. Immense stores, with nearly 300 loaded vessels,
160,000 stand of arms, &c., were taken.
1810. James Chalmeês , printer to the city and university of Aberdeen,
and proprietor of the Aberdeen Journal, died.
1812. The Decameron of Boccacio, a single volume small folio,
printed in 1471, sold at the sale of the duke of Roxburgh's library to

the marquis of Blandford, for £2,260.
1814. Henêy Têesham died; an Irish poet and painter of merit.
1815. The allied army under Wellington fell back on Waterloo, and
Blucher to Wavre. The earl of Uxbridge made a brilliant charge of
cavalry at Gemappe.
1815. British order in council, forbidding the Americans to use the
British territories for purposes connected with the Newfoundland
fisheries.
1825. Corner stone of Bunker hill monument laid with great and
enthusiastic ceremonies; Lafayette being present.
1839. William Bentinck, an English statesman, died. He had sustained
many high public offices, was a general in the army, and ten years
governor-general of India.
1850. The steamer Griffith on lake Erie was burnt and 300 lives lost.
1852. Thçmas Buffum died, aged 75; an active man in the political
history of Rhode Island, who had filled with credit many offices of
honor and trust.
1852. Jçhn Têimble , a Kentucky judge, died, aged 69; having
sustained the character of an able and upright man.
1852. William King, first governor of Maine, died, aged 84. He
removed to Bath early in the present century, and his name is
identified most intimately with all that relates to the separation from
Massachusetts, and the adoption of the state constitution. He held
various civil offices with ability and fidelity.
1852. The city of Sonora, in California, was nearly destroyed by fire.
1854. Sewaêd Baêculç, a New York jurist of distinction, died, aged 50.
He was chosen justice of the supreme court at the first judicial
election held under the new state constitution.
1854. Jçsiah Hçlbêççk , a distinguished advocate of popular education,
died, aged 65. He was a native of Derby, Ct., and graduated at Yale

college in 1810. He was very successful in diffusing among the
young a love for the study of mineralogy and geology. He lost his life
by accidently falling into Blackrock creek, near Lynchburg, Va., while
on a geological excursion.
JUNE 18.
64. The conflagration of Rome, attributed by Nero to the Christians,
which was the ostensible cause of the first persecution. (See 24th
June.)
741. Leç III (Isaurian), emperor of Constantinople, died. He was the
son of a cobbler, and disgraced the imperial dignity by acts of
barbarity and tyranny. He was the enemy of learning and learned
men, and set fire to the valuable library of his capital, by which
30,000 volumes were destroyed, besides many of the choicest
paintings and medals.
1053. Battle of Civitella; the forces of the pope, Leo IX, routed by
Robert Guiscard, the Norman.
1314. Edwaêd II marched upon Scotland from Berwick, with his vast
army.
1429. Battle of Patray, in France; the English under Talbot defeated
by Joan of Arc, with the loss of 1,500 slain, and 1,000 taken. It was
in this conflict that the notable sir John Falstaff, considering
discretion to be the better part of valor, dropped his thirsty lance,
and ran away.
1538. Truce for 10 years between Charles V of Germany, and Francis
I of France. Hostilities were renewed three years after.
1580. The colony of Virginia discouraged with their losses and
various misfortunes embarked for England.
1588. Rçbeêt Cêçwley , a scholar, preacher and printer, died. One of
his principal works was in metre, entitled:

Pleasure and pain, heaven and hell,
Remember these four and all shall be well.
1602. The fort and store house built by Gosnold on Elizabeth island
for a settlement, was abandoned in consequence of discontents
arising among those who were to have remained in the country, and
the whole company returned to England. The ruins of this ephemeral
settlement were seen as late as 1797.
1616. Thçmas Bilsçn, a celebrated English divine, died. He was
distinguished for his eloquence as a preacher, and his learning as a
theological writer and controversialist. He was one of the two final
correctors of the present translation of the Bible.
1621. The first duel in New England fought by two servants with
sword and dagger, both of whom were wounded. For this outrage
they were sentenced to lie 24 hours with their heads and feet tied
together.
1633. Chaêles I, of England, crowned king of Scotland at Holyrood
house, by the archbishop of St. Andrews.
1667. William Rawley, an English divine, died. He was chaplain to
Charles I and II, and also to Bacon, whose works he edited.
1675. Battle of Fehrbellin; the elector Frederick William, at the head
of 6,000 cavalry, attacked the Swedish invading army under the
celebrated Wrangel, and gained a complete victory.
1684. The English court of chancery gave judgment for the king
against the governor and company of Massachusetts; their charter
was declared forfeited, and their liberties were seized into the king's
hands.
1697. Richaêd , earl of Bellomont, was appointed to succeed colonel
Fletcher as governor of New York.
1718. An earthquake extended through several inland provinces of
China, by which the gates and walls of cities were thrown down. The
city of Yong-ning-tchin was entirely swallowed up, and several

mountains were thrown over a plain to the distance of about two
leagues.
1741. Fêancis Pçuêfçuê died; a French physician and skillful herbalist.
1749. Ambêçse Philiés, an English poet, died. He wrote also for the
stage with some success, although his performances were ridiculed
by Pope.
1756. Calcutta, in India, taken by Surajah Dowla: of 146 prisoners
put into a dungeon called the "black hole," 123 were suffocated.
1756. Minorca surrendered to the French by the British general
Blakeney. The British had taken it from the Spaniards in 1708.
1757. Battle of Kolin; the Prussians under Frederick II defeated by
the Austrians under count Daun, with the loss of 8,000 killed and
wounded. Frederick lost his battle through the rash bravery of one of
his generals.
1764. Lighthouse at Sandyhook first put in operation.
1772. Geêaêd Van Swieten , a Dutch physician, died. He settled in
Vienna, where he became a distinguished practitioner, and his
memory is still held in great veneration by the profession there.
1776. Gen. Buêgçyne entered St. Johns, Canada, the Americans
having evacuated it, and burnt the fort and barracks.
1779. British West India island St. Vincent, surrendered to the
French under Romain and d'Estaing.
1783. The volcano of Skaptar Jokul, in Iceland, which had recently
become very active, poured out an immense amount of lava, which,
taking a new direction, dammed up the streams, and caused great
destruction of property and lives. After flowing several days it was
precipitated down the cataract of Stapafoss, where it filled a
profound abyss, which that great waterfall had been excavating for
ages, and thence the fiery flood continued in its course.
1783. Washingtçn announced to the governors of the several states
his intended resignation of the command of the army.

1793. British frigate La Nymphe, capt. Pellew, captured French
frigate Cleopatra, after an action of 55 minutes. French captain and
about 60 of his men killed or wounded. The British loss 25 killed, 27
wounded. This was the first capture made after the declaration of
war.
1795. Russian manifesto issued by gen. Thimothie Tutomlin, on
taking possession of Russian Poland.
1799. Second day's battle of Trebia; French under Macdonald
obliged to retire across the river by the Russians under Suwarrow.
1805. Aêthuê Muêéhy, an English dramatic writer of eminence, died.
Many of his plays still keep the stage. His translation of Tacitus is
also in common use.
1811. Ruth Pieêce, the mother of sir Benjamin Thompson, count
Rumford, died at Baldwin, Maine.
1812. United States declared war against England.
1815. Hostilities ceased between England and the United States
throughout the world.
1815. Battle of Waterloo, in the Netherlands. The forces of the two
armies are differently stated, but are supposed to have been about
75,000 each. The battle began about noon, and continued with
great obstinacy till night, when the French were completely defeated
with the loss of more than 30,000 men, 210 cannon, several military
chests, and all Napoleon's baggage. The loss of the allies was
probably upwards of 20,000. This great battle gave peace to Europe.
1823. William Cççmbe, a British author of considerable merit, died. He
did not attach his name to his works.
1832. The duke of Wellington attacked by a mob in the streets of
London—the anniversary of his victory at Waterloo.
1835. William Cçbbett, an English poetical and miscellaneous writer,
died. He was a self-taught and self-made man, who for many years

made a conspicuous figure in the politics of England, and was finally
elected to parliament.
1841. The constitution of the newly constituted state of the isthmus
of Panama publicly sworn to, and Dr. Thomas Herrara elected
president.
1848. Henêy Tççley, a consistent member of the methodist episcopal
church, the first masonic grand master in Mississippi, and a son not
only but the father of temperance in Natchez, died there, aged 75.
1848. The city of Prague, which had revolted on the 12th, was
bombarded and reduced to ruins.
1848. The Austrians defeated by the Piedmontese near Rivoli.
1848. Venice garrisoned by 13,000 Romans.
1848. Carlowitz bombarded.
1854. Henêietta Sçntag, one of first lyric artists of the day, died at
Mexico, aged about 50.
1855. The allies made a combined attack upon the Malakoff and
Redan towers, at Sebastopol, without success, and with a loss of 56
officers killed, 146 wounded and 17 prisoners; and 1,694 men killed
or missing, and 2,690 wounded.
JUNE 19.
325. The first council of Nice began and continued to 25th August;
present 318 bishops.
1215. Jçhn, king of England, signed the famous magna charta, and
the charter of the forests, in a meadow at Runnimede between
Staines and Windsor. (See 29th.)
1312. Pieês Gavestçn, the favorite of Edward II, executed. In his
elevation he was proud, overbearing and cruel, and the barons rose
up against him, and accomplished his destruction.

1566. James VI of Scotland and I of England, was born in a small
room in Edinburgh castle.
1579. Maestricht, in Holland, taken by the Spaniards under the duke
of Parma, after a siege of four months, during which about 8000
persons perished miserably. It was given up to pillage.
1619. The first assembly of Virginia met at Jamestown. The
settlements had now become so numerous that 11 corporations
appeared by their representatives to exercise the noblest function of
freemen, the power of legislation.
1690. Ezekiel Hçékins , a learned English prelate died, aged 57.
1707. William Sheêlçck, an eminent English divine, died, aged about
66; famous for his controversial works, in which he took sides
against the dissenters, as also against Dr. South on the subject of
the trinity.
1709. Isaac Paéin, a French divine, died. His views differed a hair
from those of his sect, and persecution followed him from one
country to another, till he finally took refuge with the catholics.
1715. Nichçlas Lemeêy, a French chemist, died, aged 70. He was
ardently devoted to the science, and contributed much to spread a
correct knowledge of it among the people by his lectures.
1720. Jçhn Matthews, aged about 18, was executed at Tyburn, for,
while an apprentice, printing a political work.
1729. Rçbeêt Knell, the compositor, and Jçhn Claêk, the pressman, of
Mist's Journal, were pilloried, but protected by their friends from
being pelted by the mob.
1741. Admiral Veênçn seized the castles of Carthagena, South
America. The British were afterwards compelled to retire on account
of pestilence.
1754. A convention of the states at Albany proposed a union for
defence against the common enemy. Delegates were present from

New Hampshire, Massachusetts, Rhode Island, Connecticut,
Pennsylvania, Maryland and New York.
1755. William Hay died in England; remarkable for his deformity, on
which he wrote an essay. He was a member of parliament, and an
author of some merit.
1757. Action between British ship Experiment, 20 guns, 142 men,
and French ship Telemaque, 26 guns, 460 men, in which the latter
was captured with the loss of 125 killed, 110 wounded. It had been
fitted out expressly to capture the Experiment, which had 12 killed,
36 wounded.
1781. Assault on fort Ninety-six, by the Americans under Gen.
Greene, who were repulsed with the loss of 185. The Americans
then abandoned the siege. British loss 85.
1783. Henêy Lçyd, a military officer and writer, died. He was born in
Wales, entered the service of Austria, and afterwards served in the
armies of Prussia and Russia. On his return to England he produced
several military works of great merit.
1786. Nathaniel Gêeene, an officer in the revolutionary army, died,
aged 46. He was of quaker descent, born in Rhode Island. He
distinguished himself at the battles of Trenton, Princeton,
Germantown and Monmouth, and finally covered himself with glory
at the battle of Eutaw Springs, which closed the war in South
Carolina.
1794. French general Dumçuêieê , arrived in London on his escape
from the convention, but was ordered to depart the British
dominions immediately.
1794. The Corsicans accepted their new constitution, and
acknowledged George III their king.
1794. Richaêd Henêy Lee, a revolutionary patriot, died. He originated
the first resistance to British oppression, and during the struggle
continued to hold some important civil office, where his talents were
conspicuous.

1798. Bçnaéaête left Malta at the head of the French expedition which
was destined for Egypt, leaving behind him 4,000 men under Gen.
Vaubois, to regenerate the island after the pattern of the French
republic.
1799. Third day's battle of Trebia. The French under Macdonald
crossed the river and attacked the Austrians and Russians. But after
an obstinate and bloody conflict they were compelled to fall back
with a loss of 1700 killed and 500 prisoners.
1799. Five French frigates bound from Jaffa to Toulon, with 1340
men, were captured by a British squadron.
1800. Battle of Blenheim; the French under Moreau, after a short
but obstinate action, defeated the Austrians under Gen. Starray, and
obliged them to abandon Ulm and retire into Franconia.
1807. Naval action off Lemnos between the Russians and Turks, in
which the latter were defeated with the loss of an 80 gun ship and
two other ships of the line taken, and five burnt.
1808. Action off the Nase of Norway; the British sloop Seagull sunk
by a Danish brig and several gun boats. Several of the Danes went
down with her.
1809. Congress renewed the non-intercourse act.
1811. Samuel Chase, a judge of the United States supreme court,
died. He was a distinguished member of the congress of 1774.
1813. British landed from their shipping on lake Ontario, and
destroyed the public stores at Sodus; they burnt several of the best
houses and stores in the village.
1818. Patêick Bêydçne, a Scottish traveler, died. He published a
narrative of his travels in Sicily and Malta, which has been often
republished.
1820. Jçseéh Banks, an eminent English literary and philosophical
writer, died. He made several voyages in pursuit of science, one of
which was with captain Cook.

1821. Battle of Dragashan, in Turkey, between the Greeks and Turks.
The Greeks were commanded by the brave Ypsilanti; but owing to
the treachery of the Arnauts, who abandoned their posts, the Greeks
were totally defeated, and the "sacred band" of the hetaireia, the
flower of the Greek youth, were annihilated. This affair nearly
proved fatal to the cause of the Greek revolution.
1829. Jçhn Cleves Symmes, an American officer, died. He is to be
remembered for the enthusiasm with which he maintained the
theory that the earth was hollow, with an opening at each of the
poles.
1830. Battle of Strouli, between 50,000 Algerines, Turks and Arabs,
and 25,000 French under Gen. Bourmont, in which the former were
defeated.
1853. Richaêd Taylçê, second chief of the Cherokee nation, died at
Tahleguah, Arkansas. He commanded under Gen. Jackson in the war
against the Creek Indians.
JUNE 20.
404. The illustrious Jçhn Chêysçstçm banished from his patriarchate to
the remote and desolate town of Cucusus, among the ridges of
mount Taurus, by a command of the empress Eudoxia. The day of
this his final exile was marked by the conflagration of the cathedral,
senate-house, and the adjacent buildings, and by the destruction of
the incomparable statues of the Muses from the temple of Helicon.
840. Lçuis I (Debonnaire), king of France and emperor of the West,
died. He had not sufficient ability to manage the conflicting interests
of his large dominions, and was harrassed by the rebellion of his
brothers and sons.
981. Adalbeêt, bishop of Magdeburg, died. He converted the
Sclavonians, and penetrated far into Pomerania as a Christian
missionary.

1333. Battle of Halidon hill. The regent of Scotland, six earls, and
many barons fell in the field; the fugitives were pursued by king
Edward and a party of horse, and also by lord Darcy and his Irish
auxiliaries. The slaughter is said to have exceeded that of any former
defeat.
1472. King Henêy VI of England murdered in the Tower by order of
the duke of Gloucester, afterwards Richard III, as is supposed.
1632. The patent of Maryland, designed for George Calvert, lord
Baltimore, was on his decease, filled up to his son, Cecilius Calvert.
When king Charles signed it, he gave to the new patent the name of
Maryland in honor of his queen Henrietta Maria. Lord Baltimore held
it of the crown of England as part of Windsor manor, paying yearly
forever, two Indian arrows, which may now be seen at the castle.
1649. Richaêd Bêandçn , the hereditary hangman, and the executioner
of Charles I and the earl of Strafford, died in misery. He was interred
the next day amidst execrations and vulgar insults, which he could
not feel.
1698. The summit of Carguairazo, a burning mountain near Quito,
1800 feet high, crumbled together, so that nothing more than two
enormous rocky horns of the crater's edge remained, and the
country for nearly two square miles, was desolated with liquid tufa,
and argillaceous mud, enclosing dead fishes.
1719. The Spaniards defeated the Imperialists at Franca-Villa in
Sicily, with the loss of their general, Merci, and 4000 men.
1743. Jçhn Geçêge Keysleê , a German traveler and antiquary, died. On
his visit to England he was admitted fellow of the Royal society, and
deserved it by his explication of Stonehenge.
1743. Action near Manilla, between the British ship Centurion, lord
Anson, and the Acapulco ship, the Nostra Signora de Cabadonga, 36
guns and 550 men, commanded by don Geronimo de Montoro, a
Portuguese officer. The cutter was captured, with the loss of 67
killed, 84 wounded; British loss 2 killed, 17 wounded. The property
on board this prize amounted to $1,500,000.

1747. Nadiê Shah, for some time monarch of Persia, was assassinated
by his men, whom he had designed the next day to massacre.
1752. The trustees of Georgia, finding that the province languished
under their care, and weary of the complaints of the people,
surrendered their charter to the king.
1756. Calcutta taken by Surajah Dowla, and 145 Englishmen
incarcerated in the black hole, including Holwell, the governor of
Bengal; all of whom were suffocated but 23. (See June 18.)
1779. Battle of Stono-Ferry, in which the Americans under Gen.
Lincoln were defeated, owing to the mismanagement of a part of the
forces, who did not come up. Loss 146.
1781. Cçênwallis evacuated Richmond, Virginia.
1787. Chaêles Fêedeêick Abel died; an eminent musician, whose
performances attracted much attention in Europe.
1789. The national assembly of France having been refused
admission into the usual place of meeting, assembled in the rain in a
tennis court.
1790. Titles of nobility and feudal right abolished in France.
1791. Lçuis XVI and the royal family made their escape from Paris
with the intention of proceeding to Germany, to avoid the
disturbances which threatened the country.
1792. The assembly of the sans culottes appeared in Paris with their
arms and colors.
1793. The negroes and mulattoes of cape Francois began an
indiscriminate massacre of the whites. A company of 2000 men were
sent on shore from the French fleet to arrest their depredations, but
were compelled to embark again. (See 23.)
1794. Felix Vicq d'Aziê, an eminent French physician and anatomist,
died at Paris.

1798. Jeêemy Belknaé , a Boston divine, and historian of New
Hampshire, died, aged 58. He also published two volumes of
American Biography, a work which his death abridged.
1813. British made an attack on Oswego, but were repulsed by the
militia under Col. Carr.
1815. That questionable monster, the sea-serpent, observed at
Plymouth, Mass. Its extension above the surface of the water was
supposed to be more than a hundred feet. The serpentine animal
noticed in the Norway seas is of much larger proportions, with large
blue eyes, "which looked like a couple of bright pewter plates."
1818. Jçseéh Adams, an eminent London physician and medical writer,
died.
1819. The first steam vessel which crossed the Atlantic arrived at
Liverpool.
1830. Battle between the French and Algerines, near Sidi Khalef; the
latter were defeated.
1836. Edmund Jçseéh de Sieyes, a French statesman, died, aged 88. He
long acted a conspicuous part in the affairs of France, but on the fall
of Napoleon was banished, and some years previous to his death
was reduced to a state of idiocy.
1837. William IV of England, died, aged 72. His reign was brief, but
was distinguished for various important measures of reform, and the
abolition of colonial slavery.
1837. Michigan entered the United States confederacy.
1840. Pieêêe Claude Fêancçis Daunçu, peer of France, and eight years
editor of the Journal des Savants, died at Paris, aged 79. He was a
laborious writer, in which he was distinguished by his great learning
and elegance of style.
1843. Henêy Dçggett, an officer of the revolutionary army, died at
New Haven, aged 86. He was the son of Naphtali Doggett, president

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