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Stable Cis and Trans Rotational Isomers of 1,8-Di-o-tolylnaphthalene

Clough, Roger L. and Roberts, John D. (1976) Stable Cis and Trans Rotational Isomers of 1,8-Di-o-tolylnaphthalene. Journal of the American Chemical Society, 98 (4). pp. 1018-1020. ISSN 0002-7863. doi:10.1021/ja00420a028.

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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.

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Additional Information:© 1976 American Chemical Society. Received October 17, 1975. Supported by the National Science Foundation.
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Caltech Gates and Crellin Laboratories of Chemistry5263
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Official Citation:Stable cis and trans rotational isomers of 1,8-di-o-tolylnaphthalene Roger L. Clough and John D. Roberts Journal of the American Chemical Society 1976 98 (4), 1018-1020 DOI: 10.1021/ja00420a028
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60917
Deposited By: Ruth Sustaita
Deposited On:09 Oct 2015 11:04
Last Modified:10 Nov 2021 22:41

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