The Microwave Spectrum, Structure and Dipole Moment of Cyclobutene Ozonide (2,3,7-trioxabicyclo[2.2.1]heptane)

Authors

Donald G. Borseth, University of Michigan, Ann Arbor
Primož Lorenčak, University of Michigan, Ann Arbor
Hassan M. Badawi, University of Michigan, Ann Arbor
Kurt W. Hillig, University of Michigan, Ann Arbor
R. L. Kuczkowski, University of Michigan, Ann Arbor
G. David Mendenhall, Michigan Technological University

Document Type

Article

Publication Date

11-1988

Department

Department of Chemical Engineering; Department of Chemistry

Abstract

Cyclobutene ozonide containing deuterium, ¹³C and ¹⁸O enrichment was prepared by ozonolysis of cyclobutene and via singlet molecular oxygen addition to furan. It was established that the ozonide has C_s symmetry. The structure was determined from the assignment of the microwave spectra of eight isotopic species. The peroxy bond distance of 1.492(5) Å is increased by about 0.03 Å compared with less strained monocyclic ozonides. The ring strain is also evident in several other bond distances and angles when compared with cyclopentene ozonide. The dipole moment is 2.857(2) debye.

Publisher's Statement

© 1988

Publication Title

Journal of Molecular Structure

Recommended Citation

Borseth, D., Lorenčak, P., Badawi, H., Hillig, K., Kuczkowski, R., & Mendenhall, G. (1988). The Microwave Spectrum, Structure and Dipole Moment of Cyclobutene Ozonide (2,3,7-trioxabicyclo[2.2.1]heptane). Journal of Molecular Structure, 190, 125-133. http://doi.org/10.1016/0022-2860(88)80277-1
Retrieved from: https://digitalcommons.mtu.edu/michigantech-p/5353