Abstract
A stepwise mechanism for the formation of benzene as a secondary product of a nucleophilic addition reaction to acetylene in media with increased basicity has been proposed. The cyclotrimerization of acetylene takes place as a result of the successive addition of acetylene molecules to an ethynide ion followed by cyclization of the adduct formed. The activation barriers and heats of reaction have been calculated for each of the steps in the framework of the MNDO method. The maximum barrier belongs to the step leading to the formation of a C6H6 − ring from the open-chain isomer and has a height of ∼79 kJ/mole.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1797–1800, August, 1989.
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Dolgunicheva, O.Y., Vitkovskaya, N.M., Dubnikova, F.S. et al. Quantum-chemical investigation of the mechanisms of nucleophilic addition reactions to acetylene. Russ Chem Bull 38, 1645–1648 (1989). https://doi.org/10.1007/BF00956948
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DOI: https://doi.org/10.1007/BF00956948