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. https://resolver.caltech.edu/CaltechAUTHORS:20151008-070943698
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Abstract
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.
| Item Type: | Article | |||||||||
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| Additional Information: | © 1978 American Chemical Society. Received March 7, 1977. Supported by the National Science Foundation. | |||||||||
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| Issue or Number: | 7 | |||||||||
| DOI: | 10.1021/jo00401a009 | |||||||||
| Record Number: | CaltechAUTHORS:20151008-070943698 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20151008-070943698 | |||||||||
| 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 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | Ruth Sustaita | |||||||||
| Deposited On: | 08 Oct 2015 18:10 | |||||||||
| Last Modified: | 10 Nov 2021 22:41 |
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