Examination of hydrogen-bonding interactions between dissolved solutes and alkylbenzene solvents based on Abraham model correlations derived from measured enthalpies of solvation

• Enthalpies of solution measured for 48 solutes dissolved in mesitylene.
• Enthalpies of solution measured for 81 solutes dissolved in p-xylene.
• Abraham model correlations derived for enthalpies of solvation of solutes in mesitylene.
• Abraham model correlations derived for enthalpies of solvation of solutes in p-xylene.
• Hydrogen-bonding enthalpies reported for interactions of aromatic hydrocarbons with hydrogen-bond acidic solutes.

Enthalpies of solution at infinite dilution of 48 organic solutes in mesitylene and 81 organic solutes in p-xylene were measured using isothermal solution calorimeter. Enthalpies of solvation for 92 organic vapors and gaseous solutes in mesitylene and for 130 gaseous compounds in p-xylene were determined from the experimental and literature data. Abraham model correlations are determined from the experimental enthalpy of solvation data. The derived correlations describe the experimental gas-to-mesitylene and gas-to-p-xylene solvation enthalpies to within average standard deviations of 1.87 kJ mol−1 and 2.08 kJ mol−1, respectively. Enthalpies of XH⋯π (XO, N, and C) hydrogen bond formation of proton donor solutes (alcohols, amines, chlorinated hydrocarbons etc.) with mesitylene and p-xylene were calculated based on the Abraham solvation equation. Obtained values are in good agreement with the results determined using conventional methods.