Abstract
The electronic structure of the phenol molecule in the gas phase was studied by X-ray emission spectroscopy (using the O-Kα and C-Kα spectra). MNDO calculations were performed, which made it possible to construct theoretical spectra and interpret experimental spectra. The structure of the molecular orbitals of phenol was compared with those of benzene and water. The π-interaction of the phenyl fragment with the oxygen-containing substituent was investigated. The contribution of the 2p atomic orbital of the oxygen atom to the π-HOMO of phenol is considerably less than that to lower-lying orbitals.
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V. D. Yumatov, A. V. Okotrub, G. G. Furin, and N. F. Salakhutdinov,Izv. Akad. Nauk, Ser. Khim., 1997, 1454 [Russ. Chem. Bull., 1997,46, 1389 (Engl. Transl.)].
L. N. Mazalov and V. D. Yumatov,Elektronnoe stroenie ekstragenov [Electron Structure Of Extragenes], Nauka, Novosibirsk, 1984, 200 pp. (in Russian).
V. D. Yumatov and N. F. Salakhutdinov,Izv. Akad. Nauk, Ser. Khim., 1994, 1033 [Russ. Chem. Bull., 1994,43, 968 (Engl. Transl.)].
G. G. Furin, A. V. Zibarev, L. N. Mazalov, and V. D. Yumatov,Elektronnaya struktura ftorororganicheskikh soedinenii [Electronic Structure of Organofluorine Compounds], Nauka, Novosibirsk, 1988, 264 pp. (in Russian).
K. Kimura, S. Katsumata, Y. Achiba, T. Yamazaki, and S. Iwata,Handbook of He(i)Photoelectron Spectra of Fundamental Organic Molecules, Japan Scientific Societies Press, Tokyo, Halsted Press, New York, 1981, 270 pp.
V. D. Yumatov, D. Sc. (Chemistry) Thesis, Institute of Inorganic Chemistry of Siberian Branch of the Russian Academy of Sciences, Novosibirsk, 1995, 74 pp. (in Russian).
A. V. Okotrub, V. D. Yumatov, and L. N. Mazalov,Dokl. Akad. Nauk SSSR, 1984,275, 1456 [Dokl. Chem., 1984 (Engl. Transl.)].
A. V. Okotrub, L. N. Mazalov, and V. D. Yumatov,Zh. Strukt. Khim., 1984,25, No. 6, 66 [J. Struct. Chem., 1984,25, No. 6 (Engl. Transl.)].
J. Nordgren, L. O. Werme, H. Agren, K. Nordling, and K. Siegbahn,J. Phys., B: Atom. and Mol. Phys., 1975,8, L18.
J.-E. Rubensson, L. Pettersson, N. Wassdahl, M. Bäckström, and J. Nordgren,J. Chem. Phys., 1985,82, 4486.
W. L. Jolly, K. D. Bomben, and C. J. Eyermann,Atom. Data and Nucl. Data Tables, 1984,31, 433.
T. P. Debies and J. W. Rabalais,J. Electron Spectrosc. and Relat. Phenom., 1972/73,1, 355.
M. H. Palmer, W. Moyes, and M. Spiers,J. Mol. Struct., 1979,52, 293.
H. Agren and P. S. Bagus,J. Am. Chem. Soc., 1985,107, 134.
D. Nordforst, A. Nilsson, N. Mårtensson, S. Svensson, U. Gelius, and S. Lunell,J. Chem. Phys., 1988,88, 2630.
D. Nordforst, A. Nilsson, N. Mårtensson, S. Svensson, U. Gelius, and H. Agren,J. Electron. Spectrosc. Relat. Phenom., 1991,56, 117.
A. D. Baker, D. P. May, and D. W. Turner,J. Chem. Soc., B, 1968, 22.
D. W. Turner, C. Baker, A. D. Baker, and C. R. Brundle,Molecular Photoelectron Spectroscopy, Wiley-Interscience, London-New York-Sydney-Toronto, 1970, 270.
J. P. Maier and D. W. Turner,J. Chem. Soc., Faraday Trans. 2, 1973,69, 521.
T. Kobayashi and S. Nagakura,Bull. Chem. Soc. Jpn., 1974,47, 2563.
T. Kobayashi,Phys. Lett., A, 1978,69, 105.
L. Klasinc, B. Kovač, and H. Güsten,Pure and Appl. Chem., 1983,55, 289.
T. Ohta, T. Fujikawa, and H. Kuroda,Bull. Chem. Soc. Jpn., 1975,48, 2017.
V. D. Yumatov, A. V. Okotrub, L. N. Mazalov, G. G. Furin, and G. Yakobson,J. Fluor. Chem., 1985,28, 257.
E. Gilberg, M. J. Hanus, and B. Foltz,J. Chem. Phys., 1982,76, 5093.
N. Kosuch, E. Tegeler, G. Wiech, and A. Faessler,Chem. Phys. Lett., 1977,47, 96.
C. K. Ingold,Structure and Mechanism in Organic Chemistry, 2nd Ed., Cornell University Press, Ithaca and London, 1969.
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For Part 3, see Ref. 1.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2187–2193, December, 1997.
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Yumatov, V.D., Okotrub, A.V., Furin, G.G. et al. Electronic structure of monosubstituted benzenes and X-ray emission spectroscopy. Russ Chem Bull 46, 2074–2081 (1997). https://doi.org/10.1007/BF02495254
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DOI: https://doi.org/10.1007/BF02495254