Abstract
Quantum-chemical calculation of the electron densities on the atoms and the Wiberg indexes in coumarin and 3-amino-3-hydroxy-, and 3-carboxycoumarin molecules within the CNDO/2 approximation was accomplished. The 13C NMR spectra of the indicated compounds were recorded. The effect of the nature of the substituent in the pyrone ring on the electron structures of 3-substituted coumarin derivatives was evaluated on the basis of the data obtained. The character and degree of the relationship between the chemical shifts and the electron densities on the carbon atoms were established by means of regression analysis.
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Literature Cited
G. A. Kuznetsova, Natural Coumarins and Furocoumarins [in Russian], Nauka, Leningrad (1967).
A. Katritzky and J. Lagowsky, The Chemistry of Heterocyclic Compounds [in Russian], IL, Moscow (1963).
V. P. Zvolinskii, M. E. Perel'son, and Yu. N. Sheinker, Teor. éksp. Khim., 5, 767 (1969).
M. E. Perel'son, V. P. Zvolinski, and Yu. N. Sheinker, Zh. Sheinker, Zh. Strukt. Khim., 14, 246 (1973).
L. M. Ryzhenko, M. L. Khidekel', and A. D. Shebaldova, Izv. Akad. Nauk SSSR, Ser. Khim., No. 6, 1418 (1974).
A. D. Shebaldova, L. M. Ryzhenko, M. L. Khidekel', and L. K. Kulikova, Khim.-Farm. Zh., 15, 72 (1981).
L. M. Ryzhenko and A. D. Shebaldova, The Chemistry and Technology of Heteroorganic Compounds and Polymers [in Russian], Izd. Kazansk. Univ., Kazan (1984), p. 14.
B. Rinaldi, Comput. Chem., 1, 109 (1976).
Yu. G. Struchkov and A. I. Kitaigorodskii, Dokl. Akad. Nauk SSSR, 93, 675 (1953).
R. Woodward and R. Hoffmann, Retention of Orbital Symmetry [Russian translation], Mir, Moscow (1971).
F. W. Wehrly and T. Wirthlin, Interpretation of Carbon-13 NMR Spectra, London (1978), p. 47.
A. S. Stanely, J. Org. Chem., 40, 1175 (1975).
O. A. Subbotin, P. I. Zakharov, V. A. Zagorevskii, and D. A. Zykov, Khim. Prirodn. Soedin., No. 4, 458 (1975).
N. I. Cussans and T. N. Huckerly, Tetrahedron, 31, 2587 (1975).
S. A. Sojka, J. Org. Chem., 40, 1179 (1975).
K. A. Brownly, Statistical Theory and Methodology in Science and Technology [in Russian], Nauka, Leningrad (1977).
D. Chakravarti and R. Das, J. Indian Chem. Soc., 48, 371 (1971).
P. N. Kurien and K. C. Pandua, J. Indian Chem. Soc., 11, 823 (1934).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1611–1614, December, 1988.
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Ryzhenko, L.M., Labunskaya, V.I., Ryzhenko, B.F. et al. Electron structures and 13C NMR spectra of 3-substituted coumarin derivatives. Chem Heterocycl Compd 24, 1330–1333 (1988). https://doi.org/10.1007/BF00486672
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DOI: https://doi.org/10.1007/BF00486672