| Abstract: | Quantum chemical analysis (MP2/6‐31+G*) of the pyrrole anions addition to carbon disulfide and the substitution effects therein shows that pyrrole‐2 (5)‐carbodithioates are thermodynamically the most stable compounds, while 1‐isomer obtained from the unsubstituted pyrrole is likely a kinetic product. Steric hindrances destabilize N‐adducts when a methyl substituent appears in a 2(5) position and the 2,5‐dimethyl‐1‐pyrrolecarbodithioate anion turns out to be even less stable than the 2,5‐dimethyl‐3‐pyrrolecarbodithioate anion. By contrast, pyrrole‐1‐carboxylates are calculated to be the most stable adducts of CO2 with pyrrole anions. © 2002 Wiley Periodicals, Inc. Int J Quantum Chem, 2002 |
