Electrophilic behavior of 3-methyl-2-methylthio-1,3,4-thiadiazolium salts: A multimodal theoretical approach

Abstract

The chemical reactivity of 3-methyl-2-methylthio-1,3,4-thiadiazolium salts towards a variety of nucleophiles has been examined from several theoretical points of view including thermochemical analysis of the global reactions, the evaluation of aromaticity-related parameters - ASE (Aromatic Stabilization Energy), NICS (Nucleus Independent Chemical Shift), HOMA (Harmonic Oscillator Model of Aromaticity) - for the resulting products, the qualitative application of the HSAB- (Hard- and Soft- Acid and Bases) principle, quantitative calculation of DFT- (Density Functional Theory)- derived local and group properties such as softness and philicity, as well as the estimation of interaction energies. Two well-distinguished reaction paths are characterized depending on the nucleophilicity of the reagent. ©ARKAT.