Substituent Effects on the Nature of Hydrogen Bonding in Organic Hydroperoxides and the Structure of Triphenylmethyl Hydroperoxide
Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science
It has been found that in the crystalline state in triphenylmethyl hydroperoxide the hydroperoxy group is involved in intermolecular hydrogen-bond formation of the type O-h...π, with one C...C π-bond in a benzene ring. Conformational analysis and comparison with the results of x-ray structural analysis leads us to conclude that there are very narrow limits on the possible conformations of the COOH group in tert-butyl, cumyl, 1,1-diphenylethyl, and triphenylmethyl hydroperoxides, independent of their aggregation state or the nature of the substituent attached to the COOH group.
Antonovskii, V. L.; Kosnikov, A. Yu.; Turovskii, N. A.; Timofeeva, T. V.; Lindeman, Sergey; Struchkov, Yuri T.; and Ganyushkin, A. V., "Substituent Effects on the Nature of Hydrogen Bonding in Organic Hydroperoxides and the Structure of Triphenylmethyl Hydroperoxide" (1990). Chemistry Faculty Research and Publications. 726.