Stable Cis and Trans Rotational Isomers of 1,8-Di-o-tolylnaphthalene
- Creators
- Clough, Roger L.
- Roberts, John D.
Abstract
Studies of CPK (Corey-Pauling-Koltun) or similar space-filling models suggest that there should be a very substantial barrier to a 180° rotation about the phenyl-naphthy bonds in 1,8-diphenylnaphthalene derivatives. This leads to the expectation that such compounds with a substituent at one meta position of each phenyl ring should be expected to exist as stable cis and trans isomer pairs. However, House and co-workers have shown that several such derivatives, including 1,8-bis(3-chlorophenyl)naphthalene and 1,8-bis(3-methylcarboxyphenyl)naphthalene cannot be resolved into stable configurational isomers. Further, proton NMR studies of these derivatives indicate that ΔG^≠ for rotation is 15-16 kcal/mol, which corresponds to rather rapid rotation in solution at room temperatures.
Additional Information
© 1976 American Chemical Society. Received October 17, 1975. Supported by the National Science Foundation.Additional details
- Eprint ID
- 60917
- DOI
- 10.1021/ja00420a028
- Resolver ID
- CaltechAUTHORS:20151008-115813245
- NSF
- Created
-
2015-10-09Created 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
- 5263