oa South African Journal of Chemistry - Synthesis, physical and antimicrobial studies of ferrocenyl-N-(pyridinylmethylene)anilines and ferrocenyl-N-(pyridinylmethyl)anilines : research article
|Article Title||Synthesis, physical and antimicrobial studies of ferrocenyl-N-(pyridinylmethylene)anilines and ferrocenyl-N-(pyridinylmethyl)anilines : research article|
|© Publisher:||South African Chemical Institute (SACI)|
|Journal||South African Journal of Chemistry|
|Affiliations||1 University of KwaZulu-Natal, 2 University of KwaZulu-Natal and 3 University of KwaZulu-Natal|
|Publication Date||Jan 2016|
|Pages||51 - 66|
|Keyword(s)||Antimicrobial activity, Ferrocenyl-N-(pyridinylmethyl)anilines, Ferrocenyl-N-(pyridinylmethylene)anilines, Mechanochemistry technique and Solvent-free synthesis|
Ferrocenyl-N-(pyridinylmethylene)anilines Schiff bases were synthesized by reaction of 3- or 4-ferrocenylaniline with either2-, 3-, or 4-pyridinecarboxaldehyde under solvent-free conditions via mechanochemistry technique. Products were obtained in excellent yields within 10 min of grinding. The reactions afforded a melt or gummy semi-solid that solidified to the desired Schiff bases within a short time. These Schiff bases were reduced to their corresponding amines, ferrocenyl-N-(pyridinylmethyl)anilines, with NaBH4 over neutral Al2O3 solid support via grinding. Amines were obtained in excellent yields after intermittent grinding for approximately 1 h. Herein, five novel ferrocenyl-N-(pyridinylmethylene)anilines (compounds 3, 4, 6-8) and six ferrocenyl- -(pyridinylmethyl)anilines (compounds 9-14) are reported. Compounds were characterized through FT-IR, 1H-NMR, 13C-NMR, HRMS and SC-XRD techniques. These compounds show visible solvatochromism, when UV-V is absorption was measured in polar and non-polar solvents. In changing solvent from polar to non-polar, the Schiff bases exhibited a blue shift while the amines portrayed a red shift. Electrochemical studies on these compounds reveal that redox behaviour of the iron centre is influenced by the position imine or amine groups. Antimicrobial properties of these compounds were studied for Escherichiacoli, Staphylococcus aureus, Salmonella typhimirium and Candida albicans. Highest activity was recorded against Gram-positive bacteria and fungi.
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