Studies in restricted rotation. Part I. Barrier to rotation in some 3-arylcyclohexenone derivatives

Nasipuri, Dhanonjoy ; Mukherjee, Pranab R. (1975) Studies in restricted rotation. Part I. Barrier to rotation in some 3-arylcyclohexenone derivatives Journal of the Chemical Society, Perkin Transactions 2 (5). pp. 464-467. ISSN 0300-9580

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Official URL: http://pubs.rsc.org/en/Content/ArticleLanding/1975...

Related URL: http://dx.doi.org/10.1039/P29750000464

Abstract

Temperature dependence of the n.m.r. spectra of three 2-aryl-6-oxocyclohex-1-enylacetic acid derivatives (I)-(III) has been studied and the free energy of activation of internal rotation about the aryl-cyclohexenone bond in each determined from the coalescence temperature. The 1-naphthyl derivative (I) possesses an appreciable energy barrier (ca. 22 kcal mol-1) which is lowered considerably by the introduction of a methoxy-group adjacent to the pivot bond [as in (II)]. Some plausible explanations are suggested.

Item Type:Article
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