Thermochemical and theoretical study of 2-oxazolidinone and 3-acetyl-2-oxazolidinone

Abstract

In this paper, standard molar energies of combustion of 2-oxazolidinone and 3-acetyl-2-oxazolidinone are reported. The experimental values, obtained from static-bomb combustion calorimetry, are −(1465.42±0.52)kJ·mol−1 and −(2350.86±0.84)kJ·mol−1, respectively.Using these combustion energy values, the standard molar enthalpies of formation, in crystalline phase, for the aforesaid compounds were calculated. These values were also determined, and the corresponding values are −(430.30±0.96)kJ·mol−1 and −(617.72±1.58)kJ·mol−1, respectively.The standard molar enthalpies of sublimation at T=298.15K were experimentally obtained by using the well-known Knudsen effusion method. The obtained values are (84.20±3.22)kJ·mol−1 and (82.36±1.84)kJ·mol−1, respectively.From the above experimental results, the standard molar enthalpies of formation in gas-phase of the compounds were derived. The values are: −(346.10±3.36)kJ·mol−1 and −(535.36±2.43)kJ·mol−1, respectively.To support the consistency of the experimental results presented here, enthalpies of formation in gas-phase, using the G4 composite method, were carried out as well.Experimental results suggest that the formation of intermolecular hydrogen bonds between the nitrogen (at ring’s position 3, see Fig. 1) with the oxygen (at ring’s position 2, see Fig. 1) contributes to the values of temperature and enthalpy of fusion, enthalpy of sublimation, and enthalpy of formation in solid phase.