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Geometry of 1,3‐dihalocyclobutanes by dipole moment analysis
Author(s) -
Lampman Gary M.,
Aumiller James C.
Publication year - 2005
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.20771
Subject(s) - planarity testing , dipole , planar , chemistry , molecular geometry , moment (physics) , geometry , series (stratigraphy) , ring (chemistry) , strain (injury) , crystallography , molecular physics , computational chemistry , atomic physics , physics , mathematics , molecule , quantum mechanics , medicine , paleontology , computer graphics (images) , organic chemistry , computer science , biology
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 cis ‐series, 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. © 2005 Wiley Periodicals, Inc. Int J Quantum Chem, 2006