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Regioselectivity in the Addition of Nucleophilic Reagents to 1-Alkylthio-2-polyfluoroalkylacetylenes

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Abstract

Calculations for HC≡CH, HC≡CCF3, and H3CSC≡CCF3 were carried out using the MP2(f)/6-31G(d) nonempiric quantum-chemical method. The electronic structure and charge density distribution were examined using natural bond orbitals and the results account for the differences in the direction of nucleophilic attack of the triple bond in HC≡CCF3 and H3CSC≡CCF3.

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Authors and Affiliations

  1. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanskaya ul., Kiev, 02094, Ukraine

    E. G. Kapustin, V. M. Bzhezovskii, R. Ya. Musyanovich & Yu. G. Shermolovich

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  1. E. G. Kapustin
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  2. V. M. Bzhezovskii
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  3. R. Ya. Musyanovich
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  4. Yu. G. Shermolovich
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Kapustin, E.G., Bzhezovskii, V.M., Musyanovich, R.Y. et al. Regioselectivity in the Addition of Nucleophilic Reagents to 1-Alkylthio-2-polyfluoroalkylacetylenes. Theoretical and Experimental Chemistry 36, 331–333 (2000). https://doi.org/10.1023/A:1005268528044

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