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Ab initio study of the effect of CH ··· O hydrogen bonding on the exo/endo stereoselectivity of Diels‐Alder reactions of 2‐substituted‐1,3‐dienes with sulfur dioxide
Author(s) -
Suárez D.,
López R.,
González J.,
Sordo T. L.,
Sordo J. A.
Publication year - 1996
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/(sici)1097-461x(1996)57:3<493::aid-qua23>3.0.co;2-3
Subject(s) - chemistry , stereoselectivity , ab initio , sulfur dioxide , computational chemistry , ab initio quantum chemistry methods , diels–alder reaction , sulfur , gaussian orbital , hydrogen bond , transition state , hydrogen , medicinal chemistry , organic chemistry , catalysis , molecule
Ab initio calculations at the MP 2/6‐31 G *// HF /3‐21 G * level have been carried out to study Diels‐Alder reactions of 2‐substituted‐1,3‐dienes with sulfur dioxide. The CH ··· O electrostatic interaction detected in some of the transition structures located could be decisive in the control of the exo / endo stereoselectivity of this type of reaction. © 1996 John Wiley & Sons, Inc.