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The structure and conformation ofcis-2-phenylcyclobutanecarboxylic acid andcis-3-(p-fluorophenyl)cyclobutanecarboxylic acid

 

作者: George M. Reisner,   James D. Korp,   Ivan Bernal,   Richard Fuchs,  

 

期刊: Canadian Journal of Chemistry  (NRC Available online 1983)
卷期: Volume 61, issue 7  

页码: 1422-1427

 

ISSN:0008-4042

 

年代: 1983

 

DOI:10.1139/v83-249

 

出版商: NRC Research Press

 

数据来源: NRC

 

摘要:

The structure ofcis-2-phenylcyclobutanecarboxylic acid (1) andcis-3-(p-fluorophenyl)cyclobutanecarboxylic acid (2) have been determined by X-ray diffraction methods. Crystals of1are monoclinic, space groupC2/cwitha = 15.420(8),b = 11.687(6),c = 11.226(5) Å, β = 112.45(4)°, and eight molecules in the unit cell. Crystals of2are monoclinic, space groupP21/n,a = 8.038(5),b = 5.405(4),c = 22.69(1) Å, and β = 97.30(4)°, with four molecules in the unit cell. In both compounds the cyclobutane ring is puckered, with dihedral angles of 27° and 31°. The bond joining the substituted ring atoms in1is significantly longer (1.581(2) Å) than the other three (average 1.535(2) Å), due to crowding of substituents. In2both the carboxyl and phenyl substituents are close to the bisecting geometry, whereas in1both substituents deviate from this conformation, the carboxyl more than the phenyl.

 

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