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Structural analysis of internally crowded naphthalene derivatives. peri-diphenylacenaphthene

Clough, Roger L. and Kung, W. J. and Marsh, Richard E. and Roberts, John D. (1976) Structural analysis of internally crowded naphthalene derivatives. peri-diphenylacenaphthene. Journal of Organic Chemistry, 41 (22). pp. 3603-3609. ISSN 0022-3263. https://resolver.caltech.edu/CaltechAUTHORS:20151007-073140952

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Abstract

The sterically crowded peri-diphenylacenaphthene (1) has been synthesized by an aryl-aryl coupling reaction, and its conformation in the crystal determined by x-ray diffraction. The strain induced by nonbonded interactions between the phenyl groups greatly affects the geometry of the molecule as a whole. The phenyl rings are face to face, making an angle of 57" to the naphthalene plane, and are splayed apart. The phenyl to naphthalene bonds are nearly identical in length with the interannular bonds of biphenyl and p-terphenyl, in which the aromatic rings are coplanar. A comparison is made of the structures of 1,8-diphenylnaphthalene, peri-diphenylacenaphthene, and 1,4,5,8-tetraphenylnaphthalene, which constitute a homologous series of peri-phenylnaphthalenes differing only in the arrangement of groups at one end of the molecule. Substantial deformations of angles and bond lengths in the naphthalene framework of these compounds are analyzed in terms of force vectors acting throughout the bonding skeleton. This analysis helps to explain the surprising ease of rotation about the interannular C-C bonds in these compounds. The ^1H NMR spectrum of 1 indicates that the preferred conformation in solution is analogous to that in the crystal.


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http://dx.doi.org/10.1021/jo00884a027DOIArticle
http://pubs.acs.org/doi/abs/10.1021/jo00884a027PublisherArticle
Additional Information:© 1976 American Chemical Society. Received February 3, 1976. Supported by the National Science Foundation. NDEA Title IV Fellow 1971-1974.
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Caltech Gates and Crellin Laboratories of Chemistry5243
Issue or Number:22
Record Number:CaltechAUTHORS:20151007-073140952
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20151007-073140952
Official Citation:Structural analysis of internally crowded naphthalene derivatives. peri-Diphenylacenaphthene Roger L. Clough, W. J. Kung, Richard E. Marsh, and John D. Roberts The Journal of Organic Chemistry 1976 41 (22), 3603-3609 DOI: 10.1021/jo00884a027
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60834
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:07 Oct 2015 16:17
Last Modified:03 Oct 2019 09:01

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