Abstract
The relation between the position of the charge transfer band of molecular complexes formed by p-chloranil with benzene derivatives and ionization potentials of the donor molecule was analyzed. Electronic absorption spectra of p-chloranil complexes with donor molecules possessing degenerate molecular orbitals were examined. Unlike complexes with other acceptors, such as 1,3,5-trinitrobenzene and 1,3-dinitrobenzenea, molecular complexes of p-chloranil with analogous donors were classed within a single group.
Similar content being viewed by others
References
Pryalkin, B.S., Zh. Obshch. Khim., 1982, vol. 52, no. 1, p. 139.
Pryalkin, B.S., Voprosy khimii i khimicheskogo materialovedeniya (Chemistry and Chemical Materials Science Problems), Tomsk: Tomsk. Univ., 2002, p. 122.
Pryalkin, B.S., Russ. J. Gen. Chem., 2005, vol. 75, no. 3, p. 402.
Pryalkin, B.S., Russ. J. Gen. Chem., 2009, vol. 79, no. 11, p. 2359.
Mulliken, R.S. and Person, W.B., Molecular Complexes, New York: Wiley, 1969.
Energii razryvov khimicheskikh svyazei. Potentsialy ionizatsii i srodstvo k elektronu (Dissociation Energies of Chemical Bonds. Ionization Potentials and Electron Affinities), Kondrat’ev, V.N., Ed., Moscow: Nauka, 1974.
Levin, R.D. and Lias, S.G., U.S. Dep. Commer. Nat. Bur. Stand. Nat. Stand. Ref. Data Ser., 1982, no. 71.
Vovna, V.I., Elektronnaya struktura organicheskikh soedinenii po dannym fotoelektronnoi spektroskopii (Electronic Structure of Organic Compounds according to the Data of Photoelectron Spectroscopy), Moscow: Nauka, 1991.
Vovna, V.I. and Vilesov, F.I., Usp. Foton., 1975, no. 5, p. 3.
Dwivedi, P.C., Gupta, A., and Banga, A.K., Curr. Sci., 1982, vol. 51, no. 13, p. 651.
Kuboyama, A., Tokyo Kagyo Shikensho Hokoku, 1962, vol. 57, no. 11, p. 546; Ref. Zh., Khim., 1964, no. 6 B 56.
Fukuzumi, S. and Kochi, J.K., J. Org. Chem., 1981, vol. 46, no. 21, p. 4116.
Yoshida, Z. and Kobayashi, T., Tetrahedron, 1970, vol. 26, no. 1, p. 267.
Briegleb, G., Czekalla, J., and Reuss, G., Z. Phys. Chem., 1961, vol. 30, nos. 5–6, p. 316.
Wells, C.H.J., Tetrahedron, 1966, vol. 22, no. 7, p. 1985.
Hatano, M., Tamura, N., and Kambara, S., Kogyo Kagaku Zasshi, 1967, vol. 70, no. 11, p. 2012.
Nakayama, Y., Ichikawa, Y., and Matsuo, T., Bull. Chem. Soc. Jpn., 1965, vol. 38, no. 10, p. 1674.
Hunter, T.E. and Norfolk, D.H., Spectrochim. Acta, Part A, 1969, vol. 25, no. 1, p. 193.
Moriguchi, I., Fushimi, S., and Kaneniwa, N., Chem. Pharm. Bull., 1971, vol. 19, no. 10, p. 2132.
Davis, K.M.C. and Symons, M.C.R., J. Chem. Soc., 1965, no. 3, p. 2079.
Foster, R., Hammick, D.Ll., and Placito, P.J., J. Chem. Soc., 1956, no. 10, p. 3881.
Hamed, M.M.A., El-Gyar, S.A., and El-Nady, A., Indian J. Chem., Sect. A, 1987, vol. 26, no. 9, p. 728.
Koshkin, L.V. and Filippova, T.P., Izv. Vyssh. Uchebn. Zaved., Ser. Khim. Khim. Tekhnol., 1990, vol. 33, no. 5, p. 33.
Kalnin’sh, K.K., Zh. Fiz. Khim., 1990, vol. 64, no. 8, p. 2081.
Mukherjee, D.C. and Chandra, A.K., J. Phys. Chem., 1964, vol. 68, no. 3, p. 477.
Chakrabarty, S.K. and Chandra, A.K., Naturwissenschaften, 1962, vol. 49, no. 9, p. 206.
Koshkin, L.V., Rzhevskaya, N.N., Nazarova, I.A., and Rodionova, I.M., Izv. Vyssh. Uchebn. Zaved., Ser. Khim. Khim. Tekhnol., 1982, vol. 25, no. 6, p. 686.
Simov, D., Kamenov, L., and Stoyanov, S., Khim. Geterotsikl. Soedin., 1973, no. 4, p. 497.
Rubtsov, I.V. and Yoshihara, K., J. Phys. Chem. A, 1999, vol. 103, no. 49, p. 10 202.
Core, R.H. and Wheals, B.B., Anal. Chim. Acta, 1964, vol. 30, no. 1, p. 34.
Amano, T., Kuroda, H., and Akamatu, H., Bull. Chem. Soc. Jpn., 1968, vol. 41, no. 1, p. 83.
Lokmane, E.Ya. and Freimanis, Ya.F., Izv. Akad. Nauk Latv. SSR, Ser. Khim., 1979, no. 1, p. 95.
Mikubaeva, E.V., Svarovskaya, N.V., Kobotaeva, N.S., Sirotkina, E.E., and Koval’, E.O., Materialy nauchnoprakticheskoi konferentsii “Khimiya i khimicheskaya tekhnologiya na rubezhe tysyacheletii” (Proc. Scientific-Practical Conf. “Chemistry and Chemical Technology at the Turn of Millennium), Tomsk: Tomsk. Politekh. Univ., 2000, p. 248.
Zvonkova, Z.V. and Bulgarovskaya, I.V., Itogi Nauki Tekh. Kristallokhim., 1978, vol. 13, p. 144.
Peover, M.E., Trans. Faraday Soc., 1962, vol. 58, no. 8, p. 1656.
Nogami, T., Yoshihara, K., and Nagakura, S., Bull. Chem. Soc. Jpn., 1971, vol. 44, no. 1, p. 295.
Foster, R. and Thomson, T.J., Trans. Faraday Soc., 1962, vol. 58, no. 5, p. 860.
Foster, R. and Morris, J.W., Recl. Trav. Chim. Pays-Bas, 1970, vol. 89, no. 6, p. 636.
Aloisi, G.G. and Pignataro, S., J. Chem. Soc., Faraday Trans. 1, 1973, vol. 69, no. 3, p. 534.
Landman, U., Ledwith, A., Marsh, D.G., and Williams, D.J., Macromolecules, 1976, vol. 9, no. 5, p. 833.
Shudo, K., Kobayashi, T., and Utsunomiya, C., Tetrahedron, 1977, vol. 33, no. 14, p. 1721.
Vokin, A.I. and Turchaninov, V.K., Izv. Akad. Nauk, Ser. Khim., 1995, no. 12, p. 2365.
Zweig, A., Lehnsen, J.E., and Murray, M.A., J. Am. Chem. Soc., 1963, vol. 85, no. 24, p. 3933.
Rathore, R., Lindeman, S.V., and Kochi, J.K., J. Am. Chem. Soc., 1997, vol. 119, no. 40, p. 9393.
von Meier, H., Heiss, J., Surh, H., and Müller, E., Tetrahedron, 1968, vol. 24, no. 5, p. 2307.
Voigt, E.M., J. Am. Chem. Soc., 1964, vol. 86, no. 18, p. 3611.
Foster, R., Organic Charge-Transfer Complexes, London: Academic, 1969.
Author information
Authors and Affiliations
Additional information
Original Russian Text © B.S. Pryalkin, 2013, published in Zhurnal Obshchei Khimii, 2013, Vol. 83, No. 2, pp. 249–256.
Rights and permissions
About this article
Cite this article
Pryalkin, B.S. Molecular complexes of quinones: I. π-π complexes of p-chloranil with benzene and its derivatives. Russ J Gen Chem 83, 303–310 (2013). https://doi.org/10.1134/S1070363213020126
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363213020126