Valence tautomerism and recyclisation of type B mesoionic tetrazoles: a computational study

Abstract The energy profiles for ring opening of representative type B mesoionic 2,3-diphenyl-1,2,3,4-tetrazolium-5-olates, -thiolates, -aminides and –methylides alternative recyclisation pathways are investigated using ab initio MP2 calculations. energetics initial found to be comparable all systems, but the tetrazolium-5-olates anomalous in that no reaction pathway is accessible. influence solvent explored polarised continuum model (PCM) method simulate aqueous solvation. only significant effect solvation precursors. This correlates with dipole moment disfavours valence tautomerism both kinetically thermodynamically.