ABSTRACT
This research contains the Green synthesis and characterization of some Schiff base from croton aldehyde with aniline derivatives and evaluation of their antimicrobial activity. The reaction of N-((E)-but-2-en-1-ylidene)-2,4-dinitroaniline (SSB1) and N-((E)-but-2-en-1-ylidene)- 4-nitroaniline (SSB2) were synthesized by solvent free method using mortar and pestle, with the percentage yield of 87% and 79% respectively. The percentage atom economy of the compounds (SSB1) and (SSB2) were found to be 63.26% and 52% respectively .The synthesized compounds were characterized using FT-IR and UV spectroscopic techniques .The compounds showed absorption band for C=N and C=C 1625.1 cm-1 and 1584.5 cm-1 which are characteristic of Schiff base and the UV absorption maxima indicating the electronic characteristics 335.0- 2300nm and 381.00-2.483nm The compounds were also screened for antimicrobial activities. The compound N-((E)-but-2-en-1-ylidene)-2,4-dinitroaniline (SSB1) is resistances to Staphylococcus aureus while N-((E)-but-2-en-1-ylidene)- 4-nitroaniline (SSB2) is resistances to Pseudomonas aeruginosa. The compound (SSB1) was found to be more effective against (Aspergillus furmigatus) with the zone of inhibition 28mm, 25mm, 20mm, 18mm, and 10mm than (SSB2) with respect to antifungal activity. In conclusion the methods used are simple, efficient, economical, environmentally benign and also, the Schiff base possesses antifungal properties.
TABLE OF CONTENTS
TITLE PAGE…………………………………………………………………...i
DECLARATION ii
DEDICATION iv
ACKNOWLEDGEMENT v
ABSTRACT vi
TABLE OF CONTENTS vii
LIST OF TABLES xi
LIST OF FIGURES xii
CHAPTER ONE
1.0 INTRODUCTION
1.1 Background of the Study 1
1.4. Statement of Research Problem 2
1.5. Justification 3
1.6. Aim of Research 3
1.7. Objectives 3
CHAPTER TWO
2.0 LITERATURE REVIEW
2.1 Methods of Schiff Base Synthesis 4
2.2 Conventional Method 4
2.3 Green Chemistry Method 5
2 .4 Principles of Green Chemistry 6
2.5. Schiff bases 7
2.5.1 Synthesis of Schiff bases 7
2. 6 Biological Activity of Schiff bases 7
2.7 FT IR 8
2.8 Spectrophotometer 8
2.9 UV-Visible Spectrophotometer 9
CHAPTER THREE
MATERIALS AND METHOD
3.0. Methodology 10
3.1 Materials 10
3.2 Reagents 10
3.3 Equipment 11
3.3.1 Procedure for the synthesis of N-((E)-but-2-en-1-ylidene)-2,4-dinitroaniline(SSB1) 11
3.3.2 Procedure for the synthesis of N-((E)-but-2-en-1-ylidene)-4-nitroaniline (SSB2) 12
3.4 Characterization 13
3.4.1 Thin layer chromatography (TLC) 13
3.4.3 FT-IR 14
3.5 Antimicrobial activities 14
3.5.1 The Antibacterial screening 14
3.5.2 Test for Organism 15
3.5.3 Culture Media 15
3.5.4 Determination of minimum inhibitory concentration 15
CHAPTER FOUR
4.0 Results and Discussion
4.1 Results 17
4.4 Antimicrobial Activity 19
4.5 Minimum Inhibitory Concentration (MIC) and Minimum Bactericidal Concentration (MBC) OF SSB1 20
4.6 Minimum Inhibitory Concentration (MIC) and Minimum Bactericidal Concentration (MBC) SSB2 20
4.7 Discussion of Results 21
4.8 Synthesis and Characterization 21
4.9 Antibacterial Activity 21
CHAPTER FIVE
5.0 Summary, Conclusion, and Recommendation
5.2 Conclusion 23
5.3 Recommendation 23
REFERENCES 24
APPENDICES 29
LIST OF TABLES
Table4. 1…………………………………………………………………………………….17
Table4. 2 ……………………………………………………………………………………18
Table 4.3 ………………………………………………..18
Table 4 .4 ………………………………………………………………………19
Table 4.5 ………………………………………………………..20
Table4. 6 ………………………………………………………..21
LIST OF FIGURES
Figure 1………………………………………………………………………………35
Figure 2………………………………………………………………………………35
Figure 3………………………………………………………………………………36
Figure 4………………………………………………………………………………36
CHAPTER ONE
1.0 INTRODUCTION
1.1 Background of the Study
Infectious diseases have been a major health issue for decades especially in the developing and underdeveloped countries (VanDoren. 2023). Furthermore, the ability of microorganisms to develop resistance to antibiotics make it necessary to develop newer drugs (Terreni et al., 2021). Some of the promising molecules that are proven to be effective against antibiotic resistant microorganisms are the Schiff bases (Mohammed et al., 2023).
Schiff base are compounds containing carbon-nitrogen double bond generally known as azomethine or imine linkage and are named after their discovery in 1864 by an Italian naturalized chemist, Hugo Joseph Schiff (Abubakar et al., 2022).They are structure-based compounds in which the oxygen atom of the carbonyl group (C=O) of an aldehyde or ketone is replaced by nitrogen of primary amine (Mathenjwa et al., 2018 ).Was after this discovery that the knowledge on Schiff base spread all around the world (Xiong et al., 2020). Schiff bases foam a class of important organic compounds and represent the most utilized group of organic molecules. Carbon-nitrogen double bond containing compounds have contributed significantly to progress made in science and potentially used as a fine chemicals and medical substrate. They found interest in day to day life because of the unlimited potency of the azomethine group and ease in their formation.
They are used as pigments, dyes, catalysts, intermediates in organic synthesis, and as polymer stabilizers. Schiff bases have also been shown to exhibit a broad range of biological activities, including antifungal, antibacterial, antimalarial, anticancer, anti-inflammatory, antiviral, and antipyretic properties (Oyeniyi et al., 2023). The imine (-CH=N-) group present in such compound has been shown to be critical to the biological activity, (Ashfaq et al., 2022). The mode of interaction and inhibition effectiveness of Schiff base with bacteria and fungi depends on the molecular structure of the compound (Aljahadi,et al.,2020).
Green chemistry is the utilization of a set of principles that reduces or eliminates the use or generation of hazardous substances in the design, manufacture and application of chemical products. It’s all about waste minimization of source, use of catalyst in place of reagents, using nontoxic reagents, use of renewable resources and improved atom efficiency (Abdussalam, 2020).
Green chemistry has been adopted for the well-being of human health through identification of alternative reaction conditions and solvents for much improved selectivity, energy conservation and less or no toxic waste generation, and inherently safer chemical products which may lead to the synthesis of novel and simple environmentally safe chemical processes for selective synthesis (Kar et al., 2021). The operational simplicity, environmentally friendly conditions and higher yield achieved are major benefits that meet the requirements of green chemistry, including saving energy and high efficiency (Ardila‐Fierro et al., 2021).
Therefore the green method which requires relatively less amount of solvent and energy consumption was adopted for this study.
1.4. Statement of Research Problem
The increasing prevalence of antimicrobial resistance in microorganism, such as bacteria, poses a significant threat to global public health (Uddin, et al., 2021).
. The study aims to investigate the mechanisms, factors, and patterns of resistance development among microorganisms, with a focus on understanding the genetic, environmental, and evolutionary factors contributing to this resistance. (Peterson et al., 2018 ).
1.5. Justification
Due to increase in the resistance of microbial activity to current drugs in developing countries, there is need to developed new and more potent antimicrobial drugs which help to fight and handle microbial resistance.
Schiff base are reported to possess a lot of biological activities such as antifungal, antibacterial, anticancer, and antituberculosis. (kaya et al.,2021).
1.6. Aim of Research
The aim of this research is to synthesize and characterize Schiff bases from croton aldehyde with aniline derivatives using solvents free reactions, and evaluate their antimicrobial activity.
1.7. Objectives
The objectives will be achieved through the following to:
i. Synthesize Schiff bases using croton aldehyde with aniline derivatives by solvent free method.
ii. Characterize the Schiff bases using FT-IR (Fourier Transform Infrared Spectroscopy) and UV/Visible spectrophotometry.
iii. Determine the efficiency of synthesized Schiff bases against selected bacterial pathogens.
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