Conclusions
-
1.
The predominant direction of the reaction of acetylene with a molecule of lithium hydroxide in both the dissociated and undissociated states is the formation of the molecular π complex C2H2· LiOH.
-
2.
The formation of the complex C2H2· LiOH is accompanied by significant lowering of the energy levels of the vacant π orbitals of acetylene, which creates favorable conditions for nucleophilic attack on the triple bond.
Similar content being viewed by others
Literature cited
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).
B. A. Trofimov, Z. Chem.,26, 41 (1986).
N. M. Vitkovskaya, T É. Moskovskaya, and B. A. Trofimov, Izv. Akad. Nauk SSSR, Ser. Khim., 109 (1987).
M. J. S. Dewar and W. Thiel, J. Am. Chem. Soc.,99, 4899 (1977).
M. J. S. Dewar, Chem. Brit.,11, No. 3, 97 (1975).
T. É. Moskovskaya, N. M. Vitkovskaya, and B. A. Trofimov, Izv. Akad. Nauk SSSR, Ser. Khim., 891 (1982).
R. J. Tedeschi, J. Org. Chem.,30, 3045 (1965).
R. J. Tedeschi, Acetylene-Based Chemicals from Coal and Other Natural Resources, Marcel Dekker, New York (1982).
K. N. Houk, N. G. Rondan, P. R. von Schleyer, et al., J. Am. Chera. Soc.107, 2821 (1985).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2056–2060, September, 1988.
Rights and permissions
About this article
Cite this article
Dolgunicheva, O.Y., Dubnikova, F.S., Vitkovskaya, N.M. et al. Quantum-chemical investigation of the mechanisms of reactions involving nucleophilic addition to acetylene. 4. Study of reactions in the acetylene-LIOH system. Russ Chem Bull 37, 1841–1846 (1988). https://doi.org/10.1007/BF00962500
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00962500