Abstract
Unlike theE HOMO energies, the first vertical ionization potentials (I 1) of monosubstituted ethylenes dependen not only on both the inductive and resonance effects but also on the polarizability of the substituents, which can be characterized by the σα parameters. The σ +R , σ + p , and σα parameters for 12 silicon-, germanium-, and tin-containing groups were determined using the equations relating theI 1 values and the σI, σ +R , σ + p and σα parameters of the substituents in the molecules of organic compounds. The conjugation of organoelemental substituents with the double bond is stronger than that with benzene ring; the σ +R parameters in the ethylene and benzene series are related by a linear dependence.
Similar content being viewed by others
References
A. N. Egorochkin,Usp. Khim., 1992,61, 1092 [Russ. Chem. Rev., 1992,61 (Engl. Transl.)].
A. N. Egorochkin, S. E. Skobeleva, E. T. Bogoradovsky, and T. P. Zubova,Izv. Akad. Nauk, Ser. Khim., 1994, 1041 [Russ. Chem. Bull., 1994,43, 976 (Engl. Transl.)].
A. N. Egorochkin, S. E. Skobeleva, and T. G. Mushtina,Izv. Akad. Nauk, Ser. Khim., 1995, 289 [Russ. Chem. Bull., 1995,44, 280 (Engl. Trans.)].
A. N. Egorochkin, S. E. Skobeleva, and T. G. Mushtina,Izv. Akad. Nauk, Ser. Khim., 1997, 70 [Russ. Chem. Bull., 1997,46, 65 (Engl. Transl.)].
A. N. Egorochkin, S. E., Skobeleva, T. G. Mushtina, and E. T. Bogoradovsky,Izv. Akad. Nauk, Ser. Khim., 1997, 76 [Russ. Chem. Bull., 1997,46, 71 (Engl. Transl.)].
P. S. Sennikov and A. N. Egorochkin,Usp. Khim., 1982,51, 561 [Russ. Chem. Rev., 1982,51 (Engl. Transl.)].
A. N. Egorochkin and G. A. Razuvaev,Usp. Khim., 1987,56, 1480 [Russ. Chem. Rev., 1987,56, 846 (Engl. Transl.)].
A. N. Egorochkin, M. A. Lopatin, S. E. Skobeleva, V. I. Zhun, and V. D. Sheludyakov,Metalloorg. Khim., 1988,1, 350 [Organomet. Chem. USSR, 1988,1 (Engl. Transl.)].
V. G. Barabanov, A. V. Golovin, A. A. Rodin, and A. A. Ustenko,Usp. Khim., 1992,61, 1268 [Russ. Chem. Rev., 1992,61 (Engl. Transl.)].
D. J. Nelson and P. J. Cooper,Tetrahedron Lett., 1986,27, 4693.
V. I. Nefedov and V. I. VovnaElektronnaya struktura organicheskikh i elementoorganicheskikh soedinenii [The Electronic Structure of Organic and Organoelemental Compounds], Nauka, Moscow 1989 (in Russian).
H. Bock, G. Wagner, K. Wittel, J. Saner, and D. Seebach,Chem. Ber., 1974,107, 1869.
M. M. Heaton and M. R. El-Talbi,J. Chem. Phys., 1986,85, 7198.
H. Bock and B. Solouki, inThe Chemistry of Organic Silicon Compounds, Eds. S. Patai and Z. Rappoport, Wiley, Chichester, 1989, Part 1, 555.
A. N. Egorochkin, M. A. Lopatin, and G. A. Razuvaev,Dokl. Akad. Nauk SSSR, 1988,299, 909 [Dokl. Chem., 1988 (Engl. Transl.)].
A. Schweig, U. Weidner, and G. Manuel,J. Organomet. Chem., 1973,54, 145.
A. Schweig, U. Weidner, and G. Manuel,J. Organomet. Chem., 1974,67, C4.
C. Cauletti, C. Furlani, F. Grandinetti, and D. Marton,J. Organomet Chem., 1986,315, 287.
C. G. Pitt,J. Organomet. Chem., 1973,61, 49.
V. N. Baidin, I. I. Kritskaya, M. M. Timoshenko, Yu. A. Ustynyuk, and Yu. V. Chizhov, inUspekhi fotoniki [Advances in Photonics], Izd. Leningr. Univ., Leningrad, 1983, Issue 8, 8 (in Russian).
C. Hansch, A. Leo, and R. W. Taft,Chem. Rev., 1991,91, 165.
A. N. Egorochkin, S. E. Skobeleva, and V. L. Tsvetkova,Izv. Akad. Nauk, Ser. Khim., 1993, 1383 [Russ. Chem. Bull., 1993,42, 1316 (Engl. Transl.)].
W. J. Hehre, C. -F. Pau, A. D. Headly, and R. W. Taft,J. Am. Chem. Soc., 1986,108, 1711.
R. W. Taft, I. A. Koppel, R. D. Topsom, and F. Anvia,J. Am. Chem. Soc., 1990,112, 2047.
S. Marriott and R. D. Topsom,J. Mol. Struct., 1984,106, 277.
V. I. Vovna,Elektronnaya struktura organicheskikh soedinenii po dannym fotoelektronnoi spektroskopii [The Electronic Structure of Organic Compounds According to the Photoelectron Spectroscopy Data], Nauak, Moscow, 1991 (in Russian).
J. Bromilow, R. T. C. Brownlee, R. D. Topson, and R. W. Taft,J. Am. Chem. Soc., 1976,98, 2020.
H. Bock and B. Solouki,Chem. Rev., 1995,95, 1161.
Author information
Authors and Affiliations
Additional information
Translated fromIzvestiya Akademii Nauk Seriya Khimicheskaya, No. 9, pp. 1626–1631, September, 1997.
Rights and permissions
About this article
Cite this article
Egorochkin, A.N., Skobeleva, S.E. & Mushtina, T.G. First ionization potentials and conjugation in molecules of ethylene derivatives containing organoelemental substituents of Group IV elements. Russ Chem Bull 46, 1549–1554 (1997). https://doi.org/10.1007/BF02502937
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF02502937