Synthesis and characterization of higher amino acid Schiff bases, as monosodium salts and neutral forms. Investigation of the intramolecular hydrogen bonding in all Schiff bases, antibacterial and antifungal activities of neutral forms

• Higher amino acid Schiff bases were synthesized both as monosodium salts and neutral forms.
• Phenol-imine keto-amine tautomeric equilibria was investigated by UV–vis and 1H NMR spectra.
• Antimicrobial activity of the neutral-Schiff bases was studied.

Schiff bases derived from 5-nitro-salicylaldehyde and 4-aminobutyric acid, 5-aminopentanoic acid and 6-aminohexanoic acid were synthesized both as monosodium salts (1a–3a) and neutral forms (1b–3b). The monosodium-Schiff bases were characterized by elemental analysis, 1H/13C NMR, IR, powder XRD, UV–vis spectra and conductivity measurements. The neutral-Schiff bases were characterized by elemental analysis, 1H/13C NMR, 2D NMR (HMQC), mass, IR, powder XRD, UV–vis spectra and conductivity measurements. The intramolecular hydrogen bonding and related tautomeric equilibria in all the Schiff bases were studied by UV–vis and 1H NMR spectra in solution. Additionally, the neutral-Schiff bases were screened against Staphylococcus aureus-EB18, S. aureus-ATCC 25923, Escherichia coli-ATCC 11230, Candida albicans-M3 and C. albicans-ATCC 16231.

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