Nasipuri, Dhanonjoy ; Konar, Samir K. (1979) Restricted rotation. Part 3. Barrier to rotation in methyl 2-(8-quinolyl)-6-oxocyclohex-1-enylacetate: comparative study of the effective bulk of a nitrogen lone pair in quinoline and of a naphthalene hydrogen Journal of the Chemical Society, Perkin Transactions 2 (3). pp. 269-271. ISSN 0300-9580
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Official URL: http://pubs.rsc.org/en/Content/ArticleLanding/1979...
Related URL: http://dx.doi.org/10.1039/P29790000269
Abstract
The rotational free energy barrier of methyl 2-(8-quinolyl)-6-oxocyclohex-1-enylacetate (2) about the aryl-cyclohexenone bond is found to be 75.7 kJ mol-1 by dynamic n.m.r. The value is lower than that (95.4 kJ mol-1) for the corresponding 1-naphthyl derivative (1) indicating that the effective bulk of the nitrogen lone pair in quinoline is less than that of a naphthalene hydrogen. A similar study with methyl 2-(1-naphthyl)-5-oxocyclopent-1-enylacetate (4) shows that the energy barrier in this case is lower than 37.0 kJ mol-1.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Royal Society of Chemistry. |
| ID Code: | 27104 |
| Deposited On: | 08 Dec 2010 12:42 |
| Last Modified: | 08 Dec 2010 12:42 |
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