G. M. Reisner, J. Korp, I. Bernal
Jul 1, 1983
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0
Influential Citations
2
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Journal
Canadian Journal of Chemistry
Abstract
The structure of cis-2-phenylcyclobutanecarboxylic acid (1) and cis-3-(p-fluorophenyl)cyclobutanecarboxylic acid (2) have been determined by X-ray diffraction methods. Crystals of 1 are monoclinic, space group C2/c with a = 15.420(8), b = 11.687(6), c = 11.226(5) A, β = 112.45(4)°, and eight molecules in the unit cell. Crystals of 2 are monoclinic, space group P21/n, a = 8.038(5), b = 5.405(4), c = 22.69(1) A, 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 in 1 is significantly longer (1.581(2) A) than the other three (average 1.535(2) A), due to crowding of substituents. In 2 both the carboxyl and phenyl substituents are close to the bisecting geometry, whereas in 1 both substituents deviate from this conformation, the carboxyl more than the phenyl.