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An Electron Diffraction Investigation of Biphenylene

Waser, Jurg and Schomaker, Verner (1943) An Electron Diffraction Investigation of Biphenylene. Journal of the American Chemical Society, 65 (8). pp. 1451-1455. ISSN 0002-7863. doi:10.1021/ja01248a003.

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W. C. Lothrop has synthesized an aromatic hydrocarbon C_(12)H_8 to which he assigns the structure (I) and the name biphenylene. It was thought worth while to establish the structure of Lothrop's biphenylene by other than chemical means. In this we have succeeded, mainly by the electron diffraction investigation described below. Our work confirms structure (I) and in particular rules out structure (II) [chemical structure] which has been proposed by W. Baker and supported by C. A. Coulson . Biphenylene and its derivatives synthesized by Lothrop are thus the first molecules of definitely established structure to contain the interesting aromatic four-ring. They should prove very valuable for studies of orientation effects due to conjugation and to strains of the bond angles (Mills-Nixon effect). Our investigations were carried out with a 1.5-g. sample of the compound, kindly given to us by Dr. Lothrop.

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Additional Information:© 1943 American Chemical Society. Received March 26, 1943. We are indebted to Dr. Linus Pauling for helpful discussion and criticism, and to Dr. W. C. Lothrop for the sample of biphenylene.
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Gates and Crellin Laboratories of Chemistry927
Issue or Number:8
Record Number:CaltechAUTHORS:20180727-101437664
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Official Citation:An Electron Diffraction Investigation of Biphenylene Jurg Waser and Verner Schomaker Journal of the American Chemical Society 1943 65 (8), 1451-1455 DOI: 10.1021/ja01248a003
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:88321
Deposited By: George Porter
Deposited On:30 Jul 2018 20:46
Last Modified:16 Nov 2021 00:25

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