Abstract
The increment scheme for calculating chemical shifts of polysubstituted naphthalenes is based on 1- and 2-substituted heterosubgraphs which describe the main part of the substituent effect. The influence of several substituents on13C NMR chemical shifts have been described by two-particle increments corresponding to 1,2- and 2,3-ortho-disubstituted heterosubgraphs (the steric interaction of substituents in the same ring) and also to 1,4-conjugation of the substituents. Conjugation of two benzene rings required the introduction of a two-particle 1,8-heterosubgraph to the increment system. The systems of two-particle increments were obtained for polychlorinated naphthalenes, oxynaphthalenes, and polychlorinated oxynaphthalenes. Predicted13C NMR spectra of polychlorinated naphthalenes not included in the increment analysis proved to be in good agreement with independent measurements.
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L. A. Fedorov and V. I. Dostovalova,Tezdokl. VIII Vsesoyuz. konf. Ispol'zovanie vychisliteinykh mashin v spektroskopii molekul i khimicheskikh issledovaniyakh [The VIII-th All-union Conf. on Computer Applications in the Spectroscopy of Molecules and Chemical Studies, Abstracts.], Novosibirsk, 1989, 99 (in Russian).
V. I. Dostovalova and L. A. Fedorov,Zh. Strukt. Khim., 1991,32, 62 [J. Struct. Chem., 1991,32 (Engl. Transl.).]
V. I. Dostovalova, L. A. Fedorov, and J. Paasivirta,Magn. Reson. Chem., 1991,29, 830.
V. I. Dostovalova and L. A. Fedorov,Magn. Reson. Chem., 1992,30, 1203.
V. I. Dostovalova, F. K. Velichko, R. Kh. Freidlina,Izv. Akad. Nauk SSSR, Ser. Khim., 1987, 773 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1987,36, 701 (Engl. Transl.)].
V. I. Dostovalova, F. K. Velichko, R. A. Amriev, O. P. Bondarenko, and R. Kh. Freidlina,Izv. Akad. Nauk SSSR, Ser. Khim., 1987, 2719 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1987,36, 2521 (Engl. Transl.)].
V. I. Dostovalova, T. T. Vasil'eva, and F. K. Velichko.Izv. Akad. Nauk SSSR, Ser. Khim., 1988, 2770 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1988,37, 2494 (Engl. Transl.)].
N. K. Wilson and R. D. Zehr,J. Org. Chem., 1978,43, 1768.
V. A. Nikiforov, R. H. Wightmen, P. Auger, M. Malaiyandi and D. Williams,Extended abstracts of 12th International Symposium on dioxins and related compounds, Tampere, Finland, 1992,8, 123.
L. Ernst,Chem. Ber., 1975,108, 2030.
J. Seita, J. Sandstrom, and T. Drakenberg,Org. Magn. Reson., 1978,11, 239.
A. N. Tikhonov and I. Ya. Arsenin,Metody Resheniya Nekorrektnykh Zadach [Methods for Solving Incorrect Problems], Nauka, Moscow, 1974, 224 p.
V. I. Dostovalova, L. A. Fedorov, and J. Paasivirta,Extended abstracts of 12th International Symposium on dioxins and related compounds, Tampere, Finland, 1992,8, 39.
V. I. Dostovalova and L. A. Fedorov,Short papers of the 10th International Meeting on chlorinated dioxins and related compounds, Bayreuth, FRG, 1990,2, 125.
V. I. Dostovalova, L. A. Fedorov, O. V. Arapov, and O. Yu. Malov,Abstracts of the 11th International Symposium on chlorinated dioxins and related compounds, Research Triangle Park, USA, 1991, Rep. P176.
V. I. Dostovalova, L. A. Fedorov, Yu. Knuutinen, E. Kolekhmainen, and Ya. Paasivirta,Izv. Akad. Nauk, Ser. Khim., 1994, 617 [Rus. Chem. Bull, 1994,43 (Engl. Transl.)].
L. Ernst,J. Magn. Res., 1976,22, 279.
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp.625–628, April, 1994.
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Dostovalova, V.I., Fedorov, L.A. Structures of polychlorinated naphthalenes and oxynaphthalenes and their13C NMR chemical shifts. Russ Chem Bull 43, 574–577 (1994). https://doi.org/10.1007/BF00699826
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DOI: https://doi.org/10.1007/BF00699826