Computational investigation of catalytic effects of CX₃COOH (X = F,Cl,H) on the three-component cyclocondensation reaction

The mechanism of acetic acid (AA), trifluoroacetic acid (TFA), and trichloroacetic acid (TCA) catalyzed three-component cyclocondensation reaction to (4S,6S)-4,6-diphenyl-1,3,5-triazinane-2-thione was determined via density functional calculations. Based on the potential energy surface diagram, TCA was found to be a reasonable catalyst [energy span (δG) is 2 kcal mol⁻¹ less than TFA and AA] for the reaction. An energetic span model implies that TFA and AA show the same catalytic performance. The impact of the presence of halogen atoms in TFA and TCA catalysts is quantified via energy barriers. [Figure not available: see fulltext.].