Structure, Basicity, and Thermodynamic Properties of 3,5-Bis(trifluoromethyl)-1,2,4-triazole with Regard to 1,2,4-Triazole: The Trifluoromethylation Effect

Abstract

Thermodynamic properties (enthalpies of sublimation, gas-phasebasicity) of 3,5-bis (trifluoromethyl)- 1,2,4-triazole have been measured. These properties are discussed in the larger frame work of two o the rtriazoles, the parent compoundand 3(5)-(trifluoromethyl)-l,2,4-triazole, thanks to abinitio calculations atthe MP2/6-3lG*//6-31G* level of accuracy. The calculations provide(i) an excellent description of the vibrational frequencies of 1H-1,2,4-triazole (ii) age o metry for this compound more consistent with the microwaveresults;(iii)adescription of the trifluoromethyl group as a substituentintheazoleseries;(iv)anexcellentaccord with the experimental protonaffinity, and(v) an understanding of the interesting properties of the title compound.