Conformational and related studies of α-mercuricyclohexanones by 1H, 13C, and 199Hg nuclear magnetic resonance

Kitching W. and Drew G.M. (1981) Conformational and related studies of α-mercuricyclohexanones by 1H, 13C, and 199Hg nuclear magnetic resonance. Journal of Organic Chemistry, 46 13: 2695-2706.

Author Kitching W.
Drew G.M.
Title Conformational and related studies of α-mercuricyclohexanones by 1H, 13C, and 199Hg nuclear magnetic resonance
Journal name Journal of Organic Chemistry   Check publisher's open access policy
ISSN 0022-3263
Publication date 1981-01-01
Sub-type Article (original research)
Open Access Status Not yet assessed
Volume 46
Issue 13
Start page 2695
End page 2706
Total pages 12
Subject 1605 Policy and Administration
Abstract Two series of α-mercuricyclohexanones (RHgCl and R2Hg) have been prepared, in which R is based on cyclohexanone and its 4-methyl, 4-tert-butyl, and 4,4-dimethyl derivatives. The parent systems (in which R is cyclohexanone) are concluded on several grounds to favor strongly a conformation in which the mercuri group is axial. An estimate of the stabilizing interaction of an axially disposed HgCl with the carbonyl system is given. The 13C, 1H, and 199Hg spectra have been interpreted in terms of favored conformations and the effects of interaction of the polarized C-Hg bond and the π C=O system. A syn-axial (CH3 ↔* HgCl) interaction is concluded to be unfavorable by >1.5 kcal/mol in 4,4-dimethyl-2-chloromercuricyclohexanone and supported by studies of 3,3-dimethylcyclohexylmercuric bromide.
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Unknown

Document type: Journal Article
Sub-type: Article (original research)
Collection: Scopus Import - Archived
 
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Created: Tue, 14 Jun 2016, 10:32:12 EST by System User