Kinetics of quaternization and conformational analysis of some substituted NN-dimethylcyclohexylamines

Ramalingam, K. ; Balasubramanian , M. ; Baliah, V. (1971) Kinetics of quaternization and conformational analysis of some substituted NN-dimethylcyclohexylamines Journal of the Chemical Society B: Physical Organic . 2287- 2290. ISSN 0045-6470

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Official URL: http://www.rsc.org/Publishing/Journals/J2/article....

Related URL: http://dx.doi.org/10.1039/J29710002287

Abstract

The rates of quaternization of a number of substituted NN-dimethylcyclohexylamines with methyl iodide in methanol have been measured at 30 and 40°C, and the conformations of these compounds are analysed from the kinetic data. The conformational free-energy difference for the dimethylamino-group is found to be -2·3 kcal mol-1 at 30°C and that for the phenyl group -3·0 kcal mol-1. The kinetic data indicate that trans-3,3,5-trimethyl- and 3,3,5,5-tetramethyl-NN-dimethylcyclohexylamine exist in the non-chair conformation.

Item Type:Article
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ID Code:5111
Deposited On:18 Oct 2010 05:58
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