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The structure and conformation of 1-phenyl-2-methylcyclopropene-3-carboxylic acid andcis­2-(m-nitrophenyl)cyclopropanecarboxylic acid

 

作者: James D. Korp,   Ivan Bernal,   Richard Fuchs,  

 

期刊: Canadian Journal of Chemistry  (NRC Available online 1983)
卷期: Volume 61, issue 1  

页码: 50-56

 

ISSN:0008-4042

 

年代: 1983

 

DOI:10.1139/v83-009

 

出版商: NRC Research Press

 

数据来源: NRC

 

摘要:

The structures ofcis-2-(m-nitrophenyl)cyclopropanecarboxylic acid (1) and 1-phenyl-2-methylcyclopropene-3-carboxylic acid (2) have been determined by X-ray methods. Crystals of1are triclinic, space group, witha = 7.422,b = 8.615,c = 9.499 Å, α = 60.24, β = 63.76, γ = 71.36°, and two molecules in the unit cell. Crystals of2are monoclinic, space groupP21/c, with four molecules in a unit cell of dimensionsa = 9.345,b = 13.286,c = 8.187 Å, and β = 98.22°. The carboxyl group of1approaches the bisecting conformation. The phenyl group is 37° from this conformation, by contrast with the unhindered compound 2-(p-nitrophenyl) cyclopropyl methyl ketone. In2the carboxyl group bisects the three-membered ring, indicating that carbonyl-cyclopropene π interactions can occur if sterically allowed. The two rings are essentially coplanar, permitting maximum interaction of the phenyl group and the double bond. In both compounds, the carbonyl oxygen of the carboxyl is the nearer oxygen to the three-membered ring.

 

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