MICROWAVE SPECTRUM, STRUCTURE AND DIPOLE MOMENT OF METHYLENECYCLOPROPENE

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1986

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Ohio State University

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The microwave spectrum of the normal and two C13 isotopic species of methylenecyclopropene has been observed and analyzed. The unstable cross-conjugated hydrocarbon was prepared in a flow system by passing 2-bromomethylenecyclopropane through a heated column packed with potassium t=butoxide.1 Stark effect measurements led to a molecular electric dipole moment of 1.88±0.01 Debye, and the rotational constants yielded a heavy-atom structure as follows: C1C2=1.323±0.003,C1C3=1.441±0.006 and C3C4=1.332±0.006\AA. The structure is discussed and compared to that of cyclopropenone, which has been rederived from earlier data.2

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1 S.W. Staley and T. D. Norden, J. Am. Chem. Soc. 106, 3699 (1984). 2 J. M. Pochan, J.E. Baldwin and W. H. Flygare, J. Am. Chem. Soc. 91, 1896 (1969). Address of Taylor and Hermony: Department of Chemistry, University of Kansas, Lawrence, KS 66045 Address of Norden and Staley: Department of Chemistry, University of Nebraska, Lincoln, NE 68588


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