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1,8 Interactions in Naphthalene Derivatives. An X-Ray Structure Determination and Nuclear Magnetic Resonance Studies of 1,8-Di( bromomethyl)naphthalene

Roberts, J. B. and Sherfinski, J. S. and Marsh, Richard E. and Roberts, John D. (1974) 1,8 Interactions in Naphthalene Derivatives. An X-Ray Structure Determination and Nuclear Magnetic Resonance Studies of 1,8-Di( bromomethyl)naphthalene. Journal of Organic Chemistry, 39 (8). pp. 1152-1156. ISSN 0022-3263. http://resolver.caltech.edu/CaltechAUTHORS:20151008-153201362

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Abstract

The conformation of 1,8-di(bromomethyl)naphthalene has been determined in the crystalline state and it has been found that the molecule has essentially twofold symmetry about the C-9-C-10 bond with the bromines located above and below the plane of the ring. The carbon-bromine bonds are inclined toward one another about 10º from planes perpendicular to the naphthalene ring which contain the C-14-11 and C-8-C12 bonds. This conformation has formally nonbonded H...Br distances of 2.85 A which are substantially less than the sum of the van der Waals radii and could well indicate some degree of electrostatic binding. The strain in the molecule is largely relieved both by in-plane and out-of-plane bending of the C-1-C-11 and the C-8-C-12 bonds as well as some skeletal distortion of the ring. Low-temperature proton nmr studies of 1,8-di(bromomethyl)naphthalene and some related compounds showed no evidence of barriers to rotation about the C-1-C-11 and C-8-C-12 bonds large enough to be detectable.


Item Type:Article
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http://dx.doi.org/10.1021/jo00922a030DOIArticle
http://pubs.acs.org/doi/abs/10.1021/jo00922a030PublisherArticle
Additional Information:© 1974 American Chemical Society. Received November 13, 1973. Supported by the National Science Foundation and the Public Health Service through Research Training Grant 5T01 GM-01262-09-13CH to J. S. S.
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NSFUNSPECIFIED
U.S. Public Health Service (USPHS)5T01 GM-01262-09-13CH
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Caltech Gates and Crellin Laboratories of Chemistry4790
Record Number:CaltechAUTHORS:20151008-153201362
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20151008-153201362
Official Citation:1,8-Interactions in naphthalene derivatives. X-ray structure determination and nuclear magnetic resonance studies of 1,8-di(bromomethyl)naphthalene J. B. Robert, J. S. Sherfinski, Richard E. Marsh, and John D. Roberts The Journal of Organic Chemistry 1974 39 (8), 1152-1156 DOI: 10.1021/jo00922a030
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60931
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:10 Oct 2015 02:01
Last Modified:10 Oct 2015 02:01

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