The structure of cyclopentene oxide determined by gas phase electron diffraction

Abstract

The r g structure of cyclopentene oxide has been determined by the simultaneous least squares analysis of electron diffraction and microwave spectroscopic data. The investigation has reaffirmed previous studies indicating that the molecule prefers a boat conformation. The methylene and epoxide flap angles obtained are 152.3±2.1° and 104.7±1.0° respectively. Other structural parameters determined are: r g (C-H avg.) = 1.120±0.004 Å; r g (C-C avg.) = 1.538±0.002 Å; r g (C-O) = 1.443±0.003 Å, and r g (C-C) = 1.482±0.004 Å for the carbon-carbon bond in the three membered epoxide ring. These results compare favorably with the reported structures of ethylene oxide and cyclohexene oxide. A tentative rationalization of the unusual boat conformation is also offered.