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Ab initio study of the electronic properties of potential antagonists of the glycine receptor: 1. Transition state of the 2‐pyridone · H 2 O/2‐hydroxypyridine · H 2 O tautomeric equilibrium
Author(s) -
Michel Andrég.,
Trudel Yolaine,
Dion Claude
Publication year - 1993
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.560460118
Subject(s) - tautomer , ab initio , chemistry , glycine , molecule , computational chemistry , hydrogen bond , ab initio quantum chemistry methods , stereochemistry , organic chemistry , biochemistry , amino acid
Glycine receptor substrates are molecules potentially involved in tautomerism phenomena. This study is expected to provide information that might help understand their intrinsic reactivities; such physicochemical data would allow us to establish predictive models in a search for better antagonists. Ab initio molecular orbital studies, using 3‐21 G and 6‐31 G * basis sets, are reported for the tautomeric equilibrium of 2‐pyridone · H 2 O/2‐hydroxypyridine · H 2 O. The geometry of the transition state has also been optimized. The results show the important effect of the water molecule through the formation of hydrogen bonds. This system will be used as a prototype for the design of antagonists of the glycine receptor, a potential site for the action of new antiepileptic drugs and compounds preventing ischemic brain damage. © 1993 John Wiley & Sons, Inc.