Geometry of 1,3‐dihalocyclobutanes by dipole moment analysis

Abstract

ABSTRACT:The dipole moments of cis and trans-1,3-dichloro-, 1,3-dibromo-, and 1,3-diiodocyclobutanes were obtained. The deviation from planarity (angle of puckering) was calculated from the dipole moments. In all cases, the compounds were found to be non-planar (puckered). Although the angle strain increases slightly for a non-planar ring, the decrease in torsional strain becomes more important. For the cisseries, it was found that the angle of puckering was largest for the 1,3-diiodocyclobutane. For the trans-series the angle of puckering was the least for the 1,3-diiodocyclobutane. trans-1,3-Dibromo-1,3-dimethylcyclobutane has the least amount of puckering of all the compounds studied.

Modular chemical geometry and symbolic calculation

“…This gave the classical results reported with Wiberg 53, which included data on the dibromo compounds they had obtained, and for the other compounds that Aumiller had found (unpublished work, 1965; private communication with G. M. Lampman, May 2005). The detailed analysis in Lampman's doctoral thesis is reported in detail in this issue 54.…”