Origin of the Gauche Effect in substituted ethanes and ethenes

1,2-Disubstituted ethanes having strongly electronegative substituents prefer the gauche conformation over the usual trans form. This is not the result of an attractive interaction in the gauche form, but rather a destabilizing interaction in the trans rotamer. The interaction appears to be the resu...

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Bibliographic Details
Published in:Journal of physical chemistry (1952) 1990-09, Vol.94 (18), p.6956-6959
Main Authors: Wiberg, Kenneth B, Murcko, Mark A, Laidig, Keith E, MacDougall, Preston J
Format: Article
Language:English
Subjects:
02 PETROLEUM
023000 - Petroleum- Properties & Composition
ALKANES
ALKENES
BONDING
CALCULATION METHODS
Chemistry
CONFORMATIONAL CHANGES
ELECTRONEGATIVITY
ETHANE
Exact sciences and technology
FABRICATION
General and physical chemistry
HYDROCARBONS
JOINING
MOLECULAR STRUCTURE
ORGANIC COMPOUNDS
STEREOCHEMISTRY
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Summary:1,2-Disubstituted ethanes having strongly electronegative substituents prefer the gauche conformation over the usual trans form. This is not the result of an attractive interaction in the gauche form, but rather a destabilizing interaction in the trans rotamer. The interaction appears to be the result of the formation of bent bonds, and the lower stability of a twist bent bond over that of syn bent bond. The lower energy of cis-1,2-difluoroethene as compared to its trans form may be explained in the same way.
ISSN:0022-3654
1541-5740
DOI:10.1021/j100381a008