Synthesis, spectral studies of salicylidine-pyridines: Crystal and molecular structure of 2-[(1E)-2-aza-2-(5-methyl (2-pyridyl)ethenyl)]-4-bromobenzen-1-ol

Dal H., Suzen Y., Sahin E.

SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, vol.67, no.3-4, pp.808-814, 2007 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 67 Issue: 3-4
  • Publication Date: 2007
  • Doi Number: 10.1016/j.saa.2006.08.037
  • Journal Name: SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.808-814
  • Keywords: Schiff bases, tautomerism, HETCOR, HMBC, crystal structure, SCHIFF-BASES, ANTIMICROBIAL ACTIVITY, TAUTOMERISM, DERIVATIVES, COMPLEXES, COPPER
  • Anadolu University Affiliated: Yes

Abstract

Schiff bases derived from different meta-substituted salicylaldehyde and 5-methylaminopyridine have been synthesized and characterized by elemental analysis, FT-IR, NMR and UV-vis techniques. NMR assignments were made using H-1, C-13 NMR and aided by 2D HETCOR and HMBC heteronuclear correlation techniques. The UV-vis spectra of the compounds were found useful in understanding the existence of tautomeric equilibria [phenol-imine (O-H center dot center dot center dot N) and keto-amine (O center dot center dot center dot H-N) forms] in polar and non-polar solvents. In order to rationalize the stabilization of tautomer in solid state, X-ray structure of 2-[(1E)-2-aza-2-(5-methyl(2-pyridyl)ethenyl)]-4-bromobenzen-1-ol (6) was determined. According to our crystallographic result, it has enol-imine tautomeric form. (c) 2006 Elsevier B.V. All rights reserved.