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.
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 (1)H, (13)C 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...N) and keto-amine (O...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.
Dal
Hakan
H
Department of Chemistry, Faculty of Science, Anadolu University, 26470 Yenibağlar, Eskişehir, Turkey. hakandal@anadolu.edu.tr
Süzen
Yasemin
Y
Sahin
Ertan
E
D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D001969:Bromobenzenes / Q000138:chemical synthesis* / Q000737:chemistry; D003460:Crystallization; D008279:Magnetic Resonance Imaging; D015394:Molecular Structure; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry; D012545:Schiff Bases / Q000138:chemical synthesis* / Q000737:chemistry; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism; D014961:X-Ray Diffraction
D000447:Aldehydes; D001372:Aza Compounds; D001969:Bromobenzenes; D011725:Pyridines; D012545:Schiff Bases; C013243:salicylaldehyde