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Internal Rotation in peri-Phenylnaphthalenes

Clough, Roger L. and Roberts, John D. (1978) Internal Rotation in peri-Phenylnaphthalenes. Journal of Organic Chemistry, 43 (7). pp. 1328-1331. ISSN 0022-3263. doi:10.1021/jo00401a009.

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A 180º rotation about a phenyl-naphthyl bond is expected to be effectively blocked for derivatives of the peridiphenylnaphthalenes, in which steric requirements force the phenyl rings to assume a face-to-face conformation. However, surprisingly low rotational energy barriers have been found. The preparation and the measurement of the barrier to phenyl ring rotation of a derivative of the highly crowded 1,4,5,8-tetraphenylnaphthalene system is described. The barrier for this substance is 14.9 kcal/mol compared with 16.4 kcal/mol determined for 1,8-diphenylnaphthalene; both of these barriers are much lower compared with the 33.5 kcal/mol reported for the stereotopically similar [3,4]paracyclophane. The differences are discussed in terms of a rotational transition state having large deformations of the naphthalene ring.

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Additional Information:© 1978 American Chemical Society. Received March 7, 1977. Supported by the National Science Foundation.
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Caltech Gates and Crellin Laboratories of Chemistry5528
Issue or Number:7
Record Number:CaltechAUTHORS:20151008-070943698
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Official Citation:Internal rotation in peri-phenylnaphthalenes Roger L. Clough and John D. Roberts The Journal of Organic Chemistry 1978 43 (7), 1328-1331 DOI: 10.1021/jo00401a009
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60888
Deposited By: Ruth Sustaita
Deposited On:08 Oct 2015 18:10
Last Modified:10 Nov 2021 22:41

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