Origin of the gauche effect in substituted ethanes and ethenes
Journal Article
·
· Journal of Physical Chemistry; (United States)
- Yale Univ., New Haven, CT (USA)
- McMaster Univ., Hamilton, Ontario (Canada)
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.
- OSTI ID:
- 5383034
- Journal Information:
- Journal of Physical Chemistry; (United States), Journal Name: Journal of Physical Chemistry; (United States) Vol. 94:18; ISSN 0022-3654; ISSN JPCHA
- Country of Publication:
- United States
- Language:
- English
Similar Records
Rotational barriers. 2. Energies of alkane rotamers. An examination of gauche interactions
Steric structure of some 1,2-diaryl-substituted ethanes
Rotational barriers. 1. 1,2-dihaloethanes
Journal Article
·
Tue Nov 22 23:00:00 EST 1988
· Journal of the American Chemical Society; (USA)
·
OSTI ID:5053157
Steric structure of some 1,2-diaryl-substituted ethanes
Journal Article
·
Fri Jul 10 00:00:00 EDT 1987
· Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.); (United States)
·
OSTI ID:5736660
Rotational barriers. 1. 1,2-dihaloethanes
Journal Article
·
Thu Jun 18 00:00:00 EDT 1987
· J. Phys. Chem.; (United States)
·
OSTI ID:6137651