Conclusions
-
1.
According to the data from the quantum-chemical calculation, the vinylthio anion CH2=CHS− can be observed as a result of the direct addition of an hydrosulfide ion to acetylene with a barrier having a height ≤123 kJ/mole.
-
2.
One of the intermediate products in the reaction of acetylene with hydrogen sulfide in the presence of OH− ions is HC≡C−, which adds H2S to form the complex HC≡C−·H2S without a barrier. The CH2=CSH− anion forms from this complex with practically no barrier, and the formation of the vinylthio anion takes place with a barrier not exceeding 42 kJ/mole.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
B. A. Trofimov and S. V. Amosova, Divinyl Sulfide and Its Derivatives [in Russian], Nauka, Novosibirsk (1983).
B. A. Trofimov, Heteroatomic Derivatives of Acetylene [in Russian], Nauka, Moscow (1981).
N. M. Vitkovskaya, O. Yu. Dolgunicheva, F. S. Dubnikova, and B. A. Trofimov, Izv. Akad. Nauk SSSR, Ser. Khim., 1335 (1988).
N. M. Vitkovskaya, O. Yu. Dolgunicheva, F. S. Dubnikova, and B. A. Trofimov, Izv. Akad. Nauk SSSR, Ser. Khim., 1339 (1988).
M. J. S. Dewar and W. Thiel, J. Am. Chem. Soc.,99, 4899 (1977).
N. M. Vitkovskaya, T. é. Moskovskaya, and B. A. Trofimov, Izv. Akad. Nauk SSSR, Ser. Khim., 109 (1987).
Author information
Authors and Affiliations
Additional information
For previous communications, see [3, 4].
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1343–1345, June, 1988.
Rights and permissions
About this article
Cite this article
Vitkovskaya, N.M., Dolgunicheva, O.Y., Dubnikova, F.S. et al. Quantum-chemical investigation of the mechanisms of reactions involving nucleophilic addition to acetylene. 3. Mechanism of the formation of vinylthio anions. Russ Chem Bull 37, 1180–1182 (1988). https://doi.org/10.1007/BF00961927
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00961927