Synthesis and Characterization of New Acrylamide Derivatives and Studying Their Antibacterial Activity

composites


Introduction
Acrylamide has been distinguished as a poisonous material that induces carcinogenic, reproductive, and genotoxic influences on mammalian cells.Recently, significant work has been consecrated to developing specific programs to distinguish acrylamide in the environment and drinking water.As claimed by the EU report 1 , it is determined that the total acrylamide production capacity in the EU is between 80,000-100,000 mg/year, and the cumulative amount of acrylamide from all known sources discharged toward watercourses is 0.28 mg/day.Acrylamide is the principal component of polyacrylamides, nonpoisonous polymers that have an extensive field of employment in raw oil production processes, wastewater and drinking water treatment, paper and textile production, and treatment for preserving soil degradation, cement, and mineral processing, production of colors and cosmetic supplements and other diverse uses -photographic emulsion, coatings, and adhesives, and poly(acrylamide).A water-soluble synthetic polymer, has been significant in many applications, such as medical productions, textile coating, and building industries 1,2 .Polyacrylamides are combined with insecticides as condensation agents 3 .Hugo Schiff declared Schiff's bases in the middle of the eighteenth century 4 .They are an essential discussion of organic composites attributed to a broad spectrum of biological activities, like ant tubercular 5 , antiviral 6 , proliferative 7 , antimalarial 8 , antifungal 9 , and antibacterial 10 .The general structural characteristic of the mentioned composites is the azomethine group with the general formula where R and R 1 are aryl, alkyl, cycloalkyl, or heterocyclic-group 11 .Heterocyclic composites are shown as building blocks of some biological molecules 12 ; they usually hold five-and sevenmembered rings [13][14][15] .The Schiff bases were developed by Schiff for the initial time 16 from condensation-response to either ketones or aldehyde with primary amines through refluxing the https://doi.org/ .Oxazepine is an unsaturated non-symmetric seven-membered heterocyclic that includes O and N atoms in the first and third positions, respectively.The pericyclic cycloaddition of Schiff bases with phthalic imide, succinic imide, and 3-nitophthalic anhydride 19 develops this ring.The significance of 1,3-oxazepine is attributed to its purpose as an antispasm.For instance, numerous heterocyclic composites, such as oxazepine derivatives 20 , including oxygen and nitrogen atoms, were prepared to utilize the Schiff base process 20,21 .Biological activities like anticonvulsant and antibacterial activity showed oxazepine derivatives 22,23 .

Materials and Methods
Polymerization of Acrylamide 24 In a screw-capped polymerization bottle (3g., 0.041 moles), acrylamide was dissolved in 15 ml of ethanol, and 0.05% of ammonium persulphate was added as an initiator.The bottle was flashed with nitrogen for a few minutes inside a glove box and firmly stopped.The solution was maintained at 70℃ using a water bath.After 1 hour, the solvent was evaporated under vacuum; the product was washed three times with diethyl ether and dried in a vacuum oven at 50℃, yielding 90%, Scheme 1 shows synthesis of Schiff base and self-polymerization.

Preparation
The agar diffusion approach determined the antibacterial activity of these compounds 1,2 and 3.
Utilizing Staphylococcus aureus (G-) and Pseudomonas (G+), 5mM of these compounds were seated on an agar planted with the test organism.The plate was incubated at a suitable temperature 37C° for 24 hours.

Thermal Analysis:
Thermogravimetric analysis of compound 1 ,Fig.4, displayed four weight-loss steps.The first step, at 198°C, is attributed to the water evaporation in the compound: the weight was reduced by 97.84%.At the temperature of 248 °C, the second step is attributed to the decomposition of acrylamide bonds with glutaraldehyde and the decomposition of part of glutaraldehyde with a weight loss of 58.85%.The weight percentage was relatively small, representing the proportion of the reacted glutaraldehyde.The third step showed a loss of 50.01%at 300°C, which is due to the decomposition of acrylamide bonds forming and the residual glutaraldehyde structure.Finally, the fourth step, which showed a weight loss of 15.76% at 899°C, refers to the continued degradation of Acrylamide and the release of carbon dioxide (CO2) and the residual weight of carbon waste.
Thermogravimetric analysis of compound 7 Thermogravimetric analysis of this compound 6, Fig. 6 represented three weight loss steps: The first step, at 120.02 °C, is attributed to the water evaporation in the compound, which reduced the weight by 94.28%.The second step, at 240.1 °C, is attributed to the decomposition of Schiff base 2 bonds with the compound 6 and the decomposition of part of the compound 6, with a weighting loss of 32.06%.The weight percentage was relatively small, representing the proportion of the reacted Schiff base 2 and maliec unhydried.Finally, the third step, which showed a weight loss of 10.70% at 706.2°C, refers to the continued degradation of Schiff base 2, the release of (CO2) carbon dioxide, and the residual weight of carbon waste.The Antibacterial Activity 29, 30 .
The antibacterial activities of compounds 1, 2, and 3 were resistant to two types of bacteria, Staphylococcus aureus (gram-negative) and Pseudomonas (gram-positive), using DMSO as a solvent and used gentamicin as standard 4.The results express that compound 2 expresses higher activity than two kinds of bacteria, whereas compound 1 expresses no activity against two.All the results are displayed in Table .3and Fig. 7.

Conclusion
The test of new derivatives of polymers on the antibacterial activities of two types of bacteria work describes the synthesis of 1,3-oxazepine and selfpolymerization via a cycloaddition reaction between Schiff's bases 1,2,3 and succinic, maleic anhydride.
The antibacterial activity showed intermediate results against two types of bacteria in compression with gentamicin as a standard reference.

Published
Online First: August, 2024 https://doi.org/10.21123/bsj.2024.8556P-ISSN: 2078-8665 -E-ISSN: 2411-7986 Baghdad Science Journal This work included the preparation of new polyacrylamide derivatives of Schiff bases 1-5 and then internal polymerization to give a new heterocyclic polymer.Regarding compounds 6 and 7, there were two steps for synthesizing: the first step from two moles of the acrylamide with one mole of the glyoxal in the existence of ethanol as a solvent to afford Schiff base 2. The FT-IR spectral data of compounds 1 and 2 revealed absorption bands at 2813 and 2812 cm -1 for C-H aliphatic, and absorptions at 1676, 1674, and 1612 cm -1 are attributed to C=O amide, C=N groups, Fig. 1.

Figure 1 . 1 Comp. 2 PublishedFigure 2 . 7 Comp. 6 PublishedFigure 3 .
Figure 1.Fourier transfer Infra-Red spectra of compounds C1 and C2In the second step, the oxazepine compounds 6 and 7 were prepared by the maleic and succinic anhydride reaction with Schiff base 2 in the presence of anhydrous sodium acetate.The structure of compounds 6 and 7 was proved by FT-IR spectroscopy.The FT-IR spectra of compounds 6 Fig. 5 represented three weight loss steps.The first step, at 190.1 °C, is attributed to the water evaporation in the compound: the weight was reduced by 93.06%.At the temperature of 290.7 °C, the second step belongs to the decomposition of Schiff base 2 bonds with compound 7 and the part decomposition of compound 7 with a weighting loss of 11.29%.The weight percentage was relatively small, representing the reacted Schiff base 2 and succinic anhydride proportions.Finally, the third step, which showed a weight loss of 3.53% at 699 °C, refers to the continued degradation of Schiff base 2 and the release of carbon dioxide (CO2) and the residual weight of carbon waste.
10.21123/bsj.2024.8556P-ISSN: 2078-8665 -E-ISSN: 2411-7986 Baghdad Science Journal compound in absolute ethanol, benzene, or by any different appropriate solution for one hour or more; at times, the reaction may be stimulated with acid

Table 1 . Physical properties of the starting material and the synthetic compounds.
mp: melting point; sp: softing point;