Internal Rotation in peri-Phenylnaphthalenes
- Creators
- Clough, Roger L.
- Roberts, John D.
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.
Additional Information
© 1978 American Chemical Society. Received March 7, 1977. Supported by the National Science Foundation.Additional details
- Eprint ID
- 60888
- DOI
- 10.1021/jo00401a009
- Resolver ID
- CaltechAUTHORS:20151008-070943698
- NSF
- Created
-
2015-10-08Created from EPrint's datestamp field
- Updated
-
2021-11-10Created from EPrint's last_modified field
- Other Numbering System Name
- Caltech Gates and Crellin Laboratories of Chemistry
- Other Numbering System Identifier
- 5528