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Peri Interactions: An X-ray Crystallographic Study of the Structure of 1,8-Bis(dimethylamino)naphthalene

Einspahr, Howard and Roberts, J. B. and Marsh, Richard E. and Roberts, John D. (1973) Peri Interactions: An X-ray Crystallographic Study of the Structure of 1,8-Bis(dimethylamino)naphthalene. Acta crystallographica. Section B, Structural science, 29 (8). pp. 1611-1617. ISSN 0108-7681. doi:10.1107/S0567740873005133.

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Crystals of 1,8-bis(dimethylamino)naphthalene, C_(14)H_(18)N_2, are orthorhombic, space group P2_12_12_1, with ɑ= 12•855 (1), b= 10•110 (1), c=9•664 (1)Å and Z=4. A complete structure determination, including refinement of the positions of the hydrogen atoms, led to an R index of 0-053 and a goodness-off-it of 2.02 for 1477 reflections. The molecule adopts a conformation in which one carbon atom of each of the dimethylamino groups is eclipsed with respect to the naphthalene ring. Hindrance between the dimethylamino groups and/or resonance interactions between the dimethylamino groups and the aromatic ring are sufficiently great to distort the ring in several ways, the most conspicuous being a sizable increase in the non-bonded C(1)••• C(8) distance (2.56 Å) compared to the C(4)••• C(5) distance (2•44 A) and a twisting of the naphthalene ring into a considerably nonplanar conformation.

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Additional Information:© 1973 International Union of Crystallography. Received 11 December 1972; accepted 21 February 1973. This work was supported in part by a grant from the National Science Foundation, and in part by grant GM 16966 from the Division of General Medical Sciences, Public Health Services. We are grateful to Dr Sten Samson for assembling and maintaining the diffraction equipment and to Miss Lillian Casler for much of the illustrative work.
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U.S. Public Health Service (USPHS)GM 16966
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Caltech Division of Chemistry and Chemical Engineering4507
Issue or Number:8
Record Number:CaltechAUTHORS:20151023-125008529
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Official Citation:Einspahr, H., Robert, J.-B., Marsh, R. E. and Roberts, J. D. (1973), Peri interactions: an X-ray crystallographic study of the structure of 1,8-bis(dimethylaminonaphthalene). Acta Cryst. B, 29: 1611–1617. doi: 10.1107/S0567740873005133
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61498
Deposited By: Ruth Sustaita
Deposited On:26 Oct 2015 21:09
Last Modified:10 Nov 2021 22:49

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