Intramolecular hydrogen bonding in o-hydroxyaryl Schiff bases

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 pape...

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Bibliographic Details
Published in:Journal of physical organic chemistry 2005-08, Vol.18 (8), p.686-698
Main Author: Filarowski, Aleksander
Format: Article
Language:English
Subjects:
aromaticity
intramolecular hydrogen bonding
ketimine
o-hydroxyaryl Schiff base
proton transfer
steric effect
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Summary: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. This review features the structural, spectroscopic and quantum‐mechanical researches on the sterically modified Schiff bases.
ISSN:0894-3230
1099-1395
DOI:10.1002/poc.940