Hydrogen-bonded complexes of oxetanes and other ethers with nitric acid and with trifluoroacetic acid in [2H]trichloromethane

Abstract

Equilibrium constants for hydrogen-bonded complexation of nitric acid and trifluoroacetic acid with 3,3-pentamethyleneoxetane, oxetane, 3-phenyloxetane, tetrahydrofuran, butyl methyl ether, 3-(4-nitrophenyl)oxetane and dibenzyl ether, measured by ¹H NMR spectroscopy, are reported. Reasons for the signal broadening observed with the more strongly basic ethers with nitric acid but not with trifluoroacetic acid are discussed.