Preparation and studies of spectroscopy and determination of biological effectiveness of the new Azo derived from ethyl- 4 - aminobenzoate.pptx

تحضير وتشخيص مركبات الآزو, وفعاليتها البايولوجية

1. Preparation and studies of spectroscopy and determination of biological effectiveness of the new Azo derived from ethyl- 4 - aminobenzoate Supervised by: Assist. Prof . Dr . Hasanain A. Abdul- Majed Assist. Prof . Dr . Sadiq M. Ismail By : Jassim Hameed Daadoush Al- Waeli THE FIRST SCIENTIFIC CONFERENCE FOR POSTGRADUATE STUDIES College of Education for Pure Sciences/University of Basrah UNDER THE SLOGAN (( SCIENTIFIC RESEARCH PILLAR CREATIVITY, INNOVATION AND DEVELOPMENT)) 17-18 April 2024

2. Headlines 2 Introduction 1 Abstract 2 Preparation and diagnosis 3 4 References 5 THE FIRST SCIENTIFIC CONFERENCE FOR POSTGRADUATE STUDIES College of Education for Pure Sciences/University of Basrah Biological effectiveness

3. Introduction 3 THE FIRST SCIENTIFIC CONFERENCE FOR POSTGRADUATE STUDIES College of Education for Pure Sciences/University of Basrah Azo pigments are compounds containing a group of Azo (-N = N-) [1], at both ends of which an unstable saturated structure or a more stable aromatic due to resonance [2]. Azo compounds represent the most important category in dyes used for dyeing texture and leather. Furthermore, Azo pigments are cost-effective, desirable and easy to use [3]. The scientific revolution in the dye industry began in 1859 when scientist William Henry Birkin attended the first aromatic dyes when he tried to prepare a drug for malaria and noticed that the sediment had become colored [4]. H N=N- Ar

4. Abstract 4 The new Azo is prepared from the reaction of 2-amino-3 (4-hydroxyphenyl) propanoic acid with 4-aminobenzoate ethyl for the preparation of a new Azo (J25 )= ethyl(E)–4-((3– formyl –4–hydroxyl–5-methoxyphenyl) diazenyl ) .The compound was purified and recycled and then performed diagnostic and analytical techniques. The compound was diagnosed with infrared light and mass spectrometry. Spectrometry was performed with pH values in pH 2-12. Spectrometry of the compound (J25) was diagnosed, the biological effectiveness of the azo (J25) was studied against two types of bacteria Escherichia Coli and Staphylococcus Aureuse . The results showed the apparent effect of the compounds in inhibiting the growth of bacteria where the effect was measured by measuring the diameter of the inhibition area ethyl(E)–4-((3– formyl –4–hydroxyl–5-methoxyphenyl) diazenyl )

5. Materials and Method 5 Raw materials for interaction, solvents and reagents were obtained from Aldrichand Merck. Infrared spectrometers were recorded using KBR tablets with a SHIMADZU FT-IR-8400S device. Also visual spectrums measured by GENWAY 6305 spectrometer. Mass spectrum measured by electronic collision techniques pH measurements were performed using pH scale

6. Preparation of compound azo 6 The azo compound was prepared according to the recommended procedure [7] by taking (0.991) grams equivalent to (0.006) mol of ethyl 4-aminobenzoate and (1.086) grams equivalent to (0.006) mol of 2-amino-3 (4-hydroxyphenyl) propanoic acid and using 1.8% ww /sodium hydrodynamic. As shown in the mechanical suggestions below Scheme 1. Preparation of Azo compound (J25)

7. Acid– base properties at different pH values 7 A series of solutions were prepared for different pH values (2-12) for the concentration of Azo (0.8x10-4 M). The absorption of these solutions was recorded (using pH value in the range (320-470) nm [8].

8. Solvent effect of different polarities 8 A series of Azo solutions was prepared with a total concentration of 0.8x10-4 M with Ethanol , Methanol , Water , Acetone , DMSO , Chloroform , 1,4-Dioxane and n-Hexane , the absorbance of these solutions were recorded at range of (330-460 nm) using the solvent as blank solution Ethanol Methanol Water Acetone DMSO Chloroform 1,4-Dioxane n-Hexane

9. Results and discussion 9 The Azo is stable in normal temperature and soluble in DMF, DMSO and acetone at room temperature. Table 1 summarizes the physical properties of the prepared compound. compound Molecular formula Molecular weight (g.mol -1 ) M.P ºC Yield % Color J25 C 18 H 19 O 5 N 3 357.38 195-197 80 dark red Table 1. Physical properties for novel azo compound(J25)

10. IR- Analysis 10 The most important infrared absorption peaks matching the most important aggregates in the new Azo are displayed in Table 2. Peak at range (1450.74) cm-1 reverts to a group (N = N) of the compound (J25). Sharp peak at range (1514.12) cm -1 is due to ν (C = C ). The rest of the important totals are below.[ 9]. Table 2. Selected infrared data of azo compound (J25) compound ν(O-H)cm -1 ν(C=O)cm -1 ν(C=C)cm -1 ν(N=N)cm -1 ν(C-N)cm -1 ν(C-O)cm -1 J25 3381.21 1604.77 1514.12 1450.47 1394.53 1276.88

11. 11 Figure 1. IR spectrum of (J25). IR- Analysis

12. Mass spectrum 12 Structural diagnosis of organic molecules depends heavily on mass spectrometry [10]. For AZOs at 70 volts. Mass spectrums of the Azo at m/z = 357.3, which correspond to the molecular weight of the prepared compound [C18H19O5N3] +. Base ion peaks can be seen at m/z = 120.2 as shown in (figure 2)

13. 13 Figure 2. Mass spectra of (J25). Mass spectrum

14. Acid-Base properties 14 A series of different pH values (2-12) of the prepared compound (J25) was formed to study the acid and base effects of the solutions on the prepared compound [11] and measure the ionizing constant and the horn in the absorption range (330-470) nm. The absorption spectrum of the (0.8x10 -4 )M solution of the prepared compound is measured by different pH values (2-12) in graphical form (figure 4). Peak absorption (360 nm) in pH range (4-8), (380) nm in pH range (9-11) and (410) nm in pH range (12) representing the proton shape of the compound (J25), presence of isopsty point at (385 nm)

15. 15 Figure 3. Absorption spectra of azo compound (J25) at different pH values Acid-Base properties

16. 16 The absorption curves - the pH of the Azo (J25) are drawn to determine the constants of ionization and the horn of the Azo (J25) at a certain wavelength (360nm), as in figure (figure 4). Figure 4. The Absorbance – pH curves of Azo compound (J25 ) Acid-Base properties

17. 17 Ionization and protonation constants have been calculated (table 3). From the pH absorption curve and with the help of the half-height method, pK values were obtained by this relationship ( pK = pH at A 1/2 ) [12 ] where; A 1/2 = (AL + Amin.) / 2, AL and Amin maximum and minimum curve height respectively   Azo comp. (J25) at λ = 360 nm   A m A L A 1/2 pK 0.224 0.999 0.611 2.4 p1 0.492 1.238 0.865 11. 5 a1 0.842 0.888 0.865 9.7 a2 Table 3. The protonation and ionization constants of azo compound . p = protonation constant of H for nitrogen atom of phenol molecule, a = The ionization constant of H for hydroxyl group in phenol molecule .The suggested chemical mechanism of protonation and ionization was shown in Scheme 2 Acid-Base properties

18. 18 Scheme 2. Suggested mechanism of protonation and ionization of azo compound (J 5) Acid-Base properties

19. Effect of Solvents of Different Polarities 19 (Figure 5) displays the spectrums of the AZO (J25) in various solvents with different polarizations [13] (ethanol, methanol, water, acetone, DMSO, chloroform, 1,4-Dioxane, n-Hexane) maximum wavelength (370 nm) and ionometry and horn. From (figure 5), compound (J25). There is a blue shift at (360nm) with solvents (water). The transformation is blue (370 nm) with solvent (ethanol, methanol, acetone, chloroform and hexane). Different solvent absorption spectrums are influenced by the reciprocal effect between solvent and solvent. Table 3 presents the results

20. 20 Figure 5. Electronic spectra of azo compound J at different solvents Effect of Solvents of Different Polarities

21. 21 From the shape of the spectrum of the azo compound (J25) in different polar solvents, the results recorded in (Tables.4) were found. From the results, the maximum wavelength of the compound, the red-shift, and the blue-shift were determined. The great wavelengths and molary absorption coefficient azo compound (J25) were also recorded in all solvents as shown in the (table.5) compound (J5) λ max to 1,4-Dioxane λ max Blue shift Red shift Notes shift 380 Methanol Ethanol, , Acetone, Chloroform, and n-Hexane ------- Medium shift Table 4. Information obtained from the use of different polar solvents Solvent n-Hexane 1,4-Dioxane Chloroform Acetone Ethanol Methanol DMSO Water λ max 370 380 370 370 370 370 380 360 4 1.58 1.60 1.62 1.68 1.73 1.80 1.69 0.85 Solvent n-Hexane 1,4-Dioxane Chloroform Acetone Ethanol Methanol DMSO Water λ max 370 380 370 370 370 370 380 360 1.58 1.60 1.62 1.68 1.73 1.80 1.69 0.85 Effect of Solvents of Different Polarities

22. 22 The absorption spectrum of the compound is compared in a solvent with a low electrical insulation constant such as 1,4-dioxane to know the type of displacement λ max comp. (J25) (D-1)/(D+1)   D[18]   symbol   Solvent 370s 0.308 1.89 1 n-Hexane 380s 0.394 2.30 2 1,4-Dioxane 370s 0.655 4.80 3 Chloroform 370s 0.907 20.60 4 Acetone 370s 0.920 24.00 5 Ethanol 370s 0.942 33.60 6 Methanol 380s 0.958 46.67 7 DMSO 360w 0.975 78.30 8 Water Table 4. Solvent effect on spectra of (J25) Effect of Solvents of Different Polarities

23. 23 The plot of (D-1)/(D+1) against the λmax of azo compound (J25) gives more or less high linear relation with solvents of moderate polarities Fig. 6 Figure 6 .The relation between λ max and (D-1)/(D+1) for azo compound (J25) Effect of Solvents of Different Polarities

24. Biological effectiveness 24 The biological effectiveness of Azo (J25) against the negative Staphylococcus Aureuse and Escherichia Coli are studied. The effect of Azo (J25) is evident in inhibiting the growth of staphylococcus aureus , and has not affected Echerichia . The effect of Azo (J25) was measured by measuring the diameter of the inhibition area, which was (17) mm and which was within range (10-25) mm

25. 25 Inhibition 17 mm Non-inhibition Staphylococcus Aureuse Escherichia Coli Biological effectiveness

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27. 27 Thank you for your listening THE FIRST SCIENTIFIC CONFERENCE FOR POSTGRADUATE STUDIES College of Education for Pure Sciences/University of Basrah 17-18 April 2024