Abstract
A kinetic-thermodynamic analysis of the behavior of hydroxylamine in reactions with acetic, toluenesulfonic, diethylphosphoric, and diethylphosphonic acid 4-nitrophenyl esters was conducted. Using the Brönsted approach, it was shown that hydroxylamine is a unique α-nucleophile, and its neutral and anionic forms are powerful acyl acceptors.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
T. Bruce and S. J. Benkovic, Mechanisms of Bioorganic Reactions [Russian translation], Mir, Moscow (1970).
M. N. Hughes, H. G. Nickiin, and K. Scrimankes, J. Chem. Soc., No. 22, 3485–3487 (1971).
J. Pocker and E. Green, J. Am. Chem. Soc., 98, No. 20, 6197–6202 (1976).
N. A. Suttle and A. Williams, J. Am. Chem. Soc., Perkin Trans. 2, No. 10, 1563–1567 (1983).
M. T. Skoog and W. P. Jencks, J. Am. Chem. Soc., 106, No. 24, 7597–7607 (1984).
W. P. Jencks, Catalysis in Chemistry and Enzymology [Russian translation], Mir, Moscow (1972).
Yu. S. Simanenko, T. M. Prokop'eva, V. A. Savelova, et al., Reakts. Sposob. Org. Soedin. (Tartu), 26, No. 1, 30–54 (1989).
D. J. Hupe and W. P. Jencks, J. Am. Chem. Soc., 99, No. 2, 451–464 (1977).
L. M. Litvinenko and N. M. Oleinik, Mechanisms of Action of Organic Catalysts. Basic and Nucleophilic Catalysis [in Russian], Naukova Dumka, Kiev (1984).
A. Albert and E. P. Serjeant, Ionization Constants of Acids and Bases, Wiley, New York (1962).
Author information
Authors and Affiliations
Additional information
Translated from Teoreticheskaya i Éksperimental'naya Khimiya, Vol. 30, No. 2, pp. 75–79, March–April, 1994.
Rights and permissions
About this article
Cite this article
Simanenko, Y.S., Popov, A.F., Prokop'eva, T.M. et al. Hydroxylamine anion — an effective α-nucleophile in acyl transfer reactions. Theor Exp Chem 30, 61–64 (1994). https://doi.org/10.1007/BF00530586
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00530586