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Intramolecular hydrogen bonding in o ‐hydroxyaryl Schiff bases
Author(s) -
Filarowski Aleksander
Publication year - 2005
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.940
Subject(s) - tautomer , steric effects , chemistry , intramolecular force , hydrogen bond , computational chemistry , proton , molecule , stereochemistry , organic chemistry , physics , quantum mechanics
Abstract This review deals with selected aspects of research on o ‐hydroxyaryl Schiff bases. Special attention is given to results obtained by x‐ray, IR, UV and NMR spectroscopic methods and quantum‐mechanical calculations that allow a better understanding of the nature of o ‐hydroxyaryl Schiff bases. The paper reports on studies of sterically modified o ‐hydroxyaryl Schiff bases with an intramolecular hydrogen bond made short owing to steric repulsion. The following points are focused upon: structural and energetic analysis of the steric effect and its influence on the hydrogen bond length; proton localization and the proton transfer process; the impact of proton transfer on the chelate and phenol rings in the intramolecular hydrogen bond; a generalized scheme of tautomer equilibrium and its study with the use of experimental and theoretical methods; some discrepancies found in standard parameters for a particular tautomeric form; calculations of the potential energy curve for basic tautomer forms; influence of the steric effect on the potential curve shape; and a review of semi‐empirical and quantum‐mechanical calculations of molecular structures in the ground state. Copyright © 2005 John Wiley & Sons, Ltd.