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7890165 
Journal Article 
Solvent Dependent Prototropic Tautomerism in a Schiff Base Derived from o-Vanillin and 2-Aminobenzylalcohol 
Plyuta, N; Kokozay, V; Cauchy, T; Avarvari, N; Goreshnik, E; Petrusenko, S 
2019 
ChemistrySelect
ISSN: 2365-6549 
Wiley-Blackwell 
4 
27 
7858-7865 
English 
WOS:000476767700012 
The Schiff base H2L, namely 2-(3-methoxysalicylidene-amino)-benzyl-alcohol, 1 and its two pseudo-polymorphs H2L⋅CH3OH 2 and H2L⋅H2O 3, have been synthesized by the condensation reaction of 2-aminobenzyl alcohol and o-vanillin in different solvents. X-ray crystallographic analysis revealed that the keto-enol tautomerism of H2L in solid state exists as a complex system of three different enol, keto and zwitterionic forms in equilibrium, dependent on crystal packing forces and the crystallization solvent. The enol, keto and mixed enol-zwitterionic (roughly 1:1) forms were observed in the crystal structures of 1, 2 and 3, respectively. The crystallographic results are supported by FTIR and DFT calculations. Photophysical properties were determined in acetonitrile solution and solid state and were supported by TD-DFT studies. © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 
Crystal engineering; keto-enol tautomerism; zwitterion; salicylidene Schiff base