HYDROGEN-BONDING .11. A QUANTITATIVE-EVALUATION OF THE HYDROGEN-BOND ACIDITY OF IMIDES AS SOLUTES

A reanalysis of equilibrium constants determined by Hine et al. for the 1:1 complexation of imides with various bases in tetrachloromethane has been carried out using our previously reported method. The procedure yields average log KHAvalues for the hydrogen-bond acidity of the imides that can easily be converted into our new hydrogen bond solute acidity parameters, aH2. It is shown that the hydrogen-bond acidity of activated nitrogen acids, such as imides, can be comparable to that of oxygen acids. Examples of aH2values include maleimide (0.50), 2,2,2-trichloroethanol (0.50), tetrafluorosuccinimide (0.89), and dichloroacetic acid (0.90). © 1990, American Chemical Society. All rights reserved.