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Long-range bonding/nonbonding interactions: a donor-acceptor resonance studied by dynamic NMR.
- Source :
-
Organic letters [Org Lett] 2015 Jun 05; Vol. 17 (11), pp. 2740-3. Date of Electronic Publication: 2015 May 14. - Publication Year :
- 2015
-
Abstract
- Long-range bonding interactions were evaluated using variable-temperature NMR spectroscopy and suitable 2'-CH2X-substituted phenylpyridines (X = Me, NMe2, OMe, F). It was found that the arylpyridyl rotational barriers were lower when electronegative atoms were bound to the α carbon of the 2' moiety. This effect was ascribed to a stabilizing interaction in the transition state due to the lone pair of the heterocyclic nitrogen with the α carbon. Computational support for this hypothesis came from CCSD(T)/6-31+G(d) calculations. Steric effects of the X moiety were ruled out by comparison of the rotational barriers of analogous biphenyls.
Details
- Language :
- English
- ISSN :
- 1523-7052
- Volume :
- 17
- Issue :
- 11
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 25974178
- Full Text :
- https://doi.org/10.1021/acs.orglett.5b01152