Abstract
The structure and the relative stability of the N-, Cα-, and Cβ-anions of pyrrole, its mono- and dimethyl derivatives, and their adducts with carbon disulfide were studied by the ab initio method (MP2/6-31+G*//RHF/6-31+G*). The substituent effect on the reaction path is considered. For unsubstituted pyrrole, the stability of the adducts decreases in the series Cα > N > Cβ. The stability of the N-adducts decreases considerably in the presence of the methyl groups introduced into the α-position in view of steric interactions. Possible reasons for the experimentally observed formation of the thermodynamically less stable N-adduct of the unsubstituted pyrrole and for the absence of N-adducts in reactions of the methyl derivatives with CS2 are discussed.
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Kobychev, V.B., Vitkovskaya, N.M., Zaitseva, I.L. et al. Ab initio Study of the Reaction of Pyrrole Anions with Carbon Disulfide. Journal of Structural Chemistry 42, 536–543 (2001). https://doi.org/10.1023/A:1013173321887
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DOI: https://doi.org/10.1023/A:1013173321887