Conclusions
-
1.
A quantum-chemical study of the structure of the active phosphorylating derivatives of N-phosphorylammonium cations and zwitterions and of the model structures of N-phosphorylazides was undertaken in the MNDO approximation with the sp and spd basis sets.
-
2.
It is shown that the inclusion of the 3d Orbitals at the phosphorus atom is essential for the production of correct values for the length of the bond between the phosphorus atom and the quaternary nitrogen atom.
-
3.
According to the agreement between the results from the MNDO calculations and15N NMR spectroscopy, the length of the phosphorylammonium bond decreases appreciably in the transition from the zwitterion to the cation.
Similar content being viewed by others
Literature cited
D. M. Hayes, G. L. Kenyon, and P. A. Kollman, J. Am. Chem. Soc.,100, No. 14, 4331 (1978).
V. F. Zarytova, Advances of Science and Technology. Bioorganic Chemistry Series [in Russian], Vol. 4, Moscow (1984), p. 55.
T. V. Mal'tseva and A. A. Voityuk, Izv. Akad. Nauk SSSR, Ser. Khim., No. 2, 315 (1989).
I. P. Beletskii and K. B. Yatsimirskii, Teor. Éksp. Khim., No. 65, 675 (1987).
T. A. Modro, H. S. Rzepa, and J. Symes, J. Chem. Soc. Perkin Trans. 2, 767 (1987).
V. F. Zarytova, E. M. Ivanova, D. G. Knorre, et al., Dokl. Akad. Nauk SSSR,248, No. 5, 1124 (1979).
T. S. Godovikova, V. F. Zarytova, and L. M. Khalimskaya, Bioorg. Khim.,12, 475 (1986).
A. A. Bliznyuk and A. A. Voityuk, Zh. Strukt. Khim.,29, No. 5, 156 (1988).
M. J. S. Dawar, M. L. McKee, and H. S. Rzepa, J. Am. Chem. Soc.,100, 3607 (1978).
A. A. Bliznyuk and A. A. Voityuk, Zh. Strukt. Khim.,27, No. 4, 190 (1986).
M. I. Zhdanova, V. N. Biyushkin, V. M. Ovritskii, and L. D. Protsenko, Dokl. Akad. Nauk SSSR,291 No. 4, 859 (1986).
G. J. Bullen and P. E. Dann, Acta Crystallogr.,29, No. 2, 331 (1973).
A. R. Katrizky (ed.), Physical Methods in the Chemistry of Organic Compounds [Russian translation], Khimiya, Moscow-Leningrad (1966), p. 658.
G. A. Witanowski and E. D. Webb, Nitrogen NMR, Plenum Press, London-New York (1973), p. 404.
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya No. 6, pp. 1292–1297, June, 1989.
Rights and permissions
About this article
Cite this article
Mal'tseva, T.V., Voityuk, A.A. Structural features of labile N-phosphorylammonium zwitterions and cations according to data from MNDO calculations and15N NMR spectroscopy. Russ Chem Bull 38, 1177–1182 (1989). https://doi.org/10.1007/BF00957149
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00957149