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Theoretical analysis of pyrrole anions addition to carbon disulfide and carbon dioxide
Author(s) -
Kobychev Vladimir B.,
Vitkovskaya Nadezhda M.,
Zaytseva Irina L.,
Larionova Elena Yu.,
Trofimov Boris A.
Publication year - 2002
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.10206
Subject(s) - pyrrole , chemistry , steric effects , carbon disulfide , substituent , adduct , ion , medicinal chemistry , carbon fibers , photochemistry , organic chemistry , materials science , composite number , composite material
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 CO 2 with pyrrole anions. © 2002 Wiley Periodicals, Inc. Int J Quantum Chem, 2002