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The Molecular Structures of Glyoxal and Dimethylglyoxal by the Electron Diffraction Method

LuValle, James E. and Schomaker, Verner (1939) The Molecular Structures of Glyoxal and Dimethylglyoxal by the Electron Diffraction Method. Journal of the American Chemical Society, 61 (12). pp. 3520-3525. ISSN 0002-7863. doi:10.1021/ja01267a087.

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Extension to open chain heteroatomic aliphatic compounds of the structural investigations of the constitutional effect of different bonds upon adjacent bonds should provide useful information concerning the electronic structures and the extent of resonance in these molecules. The recent electron diffraction studies of formaldehyde and acetaldehyde have given a reliable value for the carbon-oxygen double bond distance. We have now extended the investigation of compounds containing the carbonyl group to glyoxal and dimethylglyoxal, both of which contain a pair of conjugated carbon-oxygen double bonds and present the possibility of free rotation around the carbon-carbon bond connecting the adjacent carbonyl groups. Furthermore, both substances are colored, glyoxal being the simplest colored compound whose molecules have a conjugated system. Of the compounds glyoxal, dimethylglyoxal, oxalyl chloride, oxamide, and oxalic acid, it is found that glyoxal and dimethylglyoxal are colored whereas the remaining compounds are colorless. All five of these compounds may be represented by the formula RCORCO and the difference in color between the first two compounds and the remaining three compounds suggests that there may be a structural difference between the two groups of compounds. Oxalyl chloride is now under investigation in these Laboratories by the electron diffraction method, and the X-ray study of crystals of oxamide is also under way.

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Additional Information:© 1939 American Chemical Society. Received October 23, 1939. We express our thanks to Dr. Linus Pauling for his helpful criticism and discussion and to Dr. D. P. Stevenson for assistance with the calculations and helpful discussion.
Funding AgencyGrant Number
Julius Rosenwald FellowshipUNSPECIFIED
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Gates and Crellin Laboratories of Chemistry743
Issue or Number:12
Record Number:CaltechAUTHORS:20180727-101439283
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Official Citation:The Molecular Structures of Glyoxal and Dimethylglyoxal by the Electron Diffraction Method James E. LuValle and Verner Schomaker Journal of the American Chemical Society 1939 61 (12), 3520-3525 DOI: 10.1021/ja01267a087
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:88335
Deposited By: George Porter
Deposited On:30 Jul 2018 21:03
Last Modified:16 Nov 2021 00:26

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