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Molecular complexes of quinones: I. π-π complexes of p-chloranil with benzene and its derivatives

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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.

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References

  1. Pryalkin, B.S., Zh. Obshch. Khim., 1982, vol. 52, no. 1, p. 139.

    CAS  Google Scholar 

  2. Pryalkin, B.S., Voprosy khimii i khimicheskogo materialovedeniya (Chemistry and Chemical Materials Science Problems), Tomsk: Tomsk. Univ., 2002, p. 122.

    Google Scholar 

  3. Pryalkin, B.S., Russ. J. Gen. Chem., 2005, vol. 75, no. 3, p. 402.

    Article  CAS  Google Scholar 

  4. Pryalkin, B.S., Russ. J. Gen. Chem., 2009, vol. 79, no. 11, p. 2359.

    Article  CAS  Google Scholar 

  5. Mulliken, R.S. and Person, W.B., Molecular Complexes, New York: Wiley, 1969.

    Google Scholar 

  6. 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.

    Google Scholar 

  7. Levin, R.D. and Lias, S.G., U.S. Dep. Commer. Nat. Bur. Stand. Nat. Stand. Ref. Data Ser., 1982, no. 71.

    Google Scholar 

  8. 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.

    Google Scholar 

  9. Vovna, V.I. and Vilesov, F.I., Usp. Foton., 1975, no. 5, p. 3.

    Google Scholar 

  10. Dwivedi, P.C., Gupta, A., and Banga, A.K., Curr. Sci., 1982, vol. 51, no. 13, p. 651.

    CAS  Google Scholar 

  11. Kuboyama, A., Tokyo Kagyo Shikensho Hokoku, 1962, vol. 57, no. 11, p. 546; Ref. Zh., Khim., 1964, no. 6 B 56.

    CAS  Google Scholar 

  12. Fukuzumi, S. and Kochi, J.K., J. Org. Chem., 1981, vol. 46, no. 21, p. 4116.

    Article  CAS  Google Scholar 

  13. Yoshida, Z. and Kobayashi, T., Tetrahedron, 1970, vol. 26, no. 1, p. 267.

    Article  CAS  Google Scholar 

  14. Briegleb, G., Czekalla, J., and Reuss, G., Z. Phys. Chem., 1961, vol. 30, nos. 5–6, p. 316.

    Article  CAS  Google Scholar 

  15. Wells, C.H.J., Tetrahedron, 1966, vol. 22, no. 7, p. 1985.

    Article  CAS  Google Scholar 

  16. Hatano, M., Tamura, N., and Kambara, S., Kogyo Kagaku Zasshi, 1967, vol. 70, no. 11, p. 2012.

    Article  CAS  Google Scholar 

  17. Nakayama, Y., Ichikawa, Y., and Matsuo, T., Bull. Chem. Soc. Jpn., 1965, vol. 38, no. 10, p. 1674.

    Article  CAS  Google Scholar 

  18. Hunter, T.E. and Norfolk, D.H., Spectrochim. Acta, Part A, 1969, vol. 25, no. 1, p. 193.

    Article  CAS  Google Scholar 

  19. Moriguchi, I., Fushimi, S., and Kaneniwa, N., Chem. Pharm. Bull., 1971, vol. 19, no. 10, p. 2132.

    Article  CAS  Google Scholar 

  20. Davis, K.M.C. and Symons, M.C.R., J. Chem. Soc., 1965, no. 3, p. 2079.

    Google Scholar 

  21. Foster, R., Hammick, D.Ll., and Placito, P.J., J. Chem. Soc., 1956, no. 10, p. 3881.

    Google Scholar 

  22. Hamed, M.M.A., El-Gyar, S.A., and El-Nady, A., Indian J. Chem., Sect. A, 1987, vol. 26, no. 9, p. 728.

    Google Scholar 

  23. Koshkin, L.V. and Filippova, T.P., Izv. Vyssh. Uchebn. Zaved., Ser. Khim. Khim. Tekhnol., 1990, vol. 33, no. 5, p. 33.

    CAS  Google Scholar 

  24. Kalnin’sh, K.K., Zh. Fiz. Khim., 1990, vol. 64, no. 8, p. 2081.

    Google Scholar 

  25. Mukherjee, D.C. and Chandra, A.K., J. Phys. Chem., 1964, vol. 68, no. 3, p. 477.

    Article  CAS  Google Scholar 

  26. Chakrabarty, S.K. and Chandra, A.K., Naturwissenschaften, 1962, vol. 49, no. 9, p. 206.

    Article  CAS  Google Scholar 

  27. 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.

    CAS  Google Scholar 

  28. Simov, D., Kamenov, L., and Stoyanov, S., Khim. Geterotsikl. Soedin., 1973, no. 4, p. 497.

    Google Scholar 

  29. Rubtsov, I.V. and Yoshihara, K., J. Phys. Chem. A, 1999, vol. 103, no. 49, p. 10 202.

    Article  CAS  Google Scholar 

  30. Core, R.H. and Wheals, B.B., Anal. Chim. Acta, 1964, vol. 30, no. 1, p. 34.

    Google Scholar 

  31. Amano, T., Kuroda, H., and Akamatu, H., Bull. Chem. Soc. Jpn., 1968, vol. 41, no. 1, p. 83.

    Article  CAS  Google Scholar 

  32. Lokmane, E.Ya. and Freimanis, Ya.F., Izv. Akad. Nauk Latv. SSR, Ser. Khim., 1979, no. 1, p. 95.

    Google Scholar 

  33. 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.

    Google Scholar 

  34. Zvonkova, Z.V. and Bulgarovskaya, I.V., Itogi Nauki Tekh. Kristallokhim., 1978, vol. 13, p. 144.

    Google Scholar 

  35. Peover, M.E., Trans. Faraday Soc., 1962, vol. 58, no. 8, p. 1656.

    Article  CAS  Google Scholar 

  36. Nogami, T., Yoshihara, K., and Nagakura, S., Bull. Chem. Soc. Jpn., 1971, vol. 44, no. 1, p. 295.

    Article  CAS  Google Scholar 

  37. Foster, R. and Thomson, T.J., Trans. Faraday Soc., 1962, vol. 58, no. 5, p. 860.

    Article  CAS  Google Scholar 

  38. Foster, R. and Morris, J.W., Recl. Trav. Chim. Pays-Bas, 1970, vol. 89, no. 6, p. 636.

    Article  CAS  Google Scholar 

  39. Aloisi, G.G. and Pignataro, S., J. Chem. Soc., Faraday Trans. 1, 1973, vol. 69, no. 3, p. 534.

    Article  CAS  Google Scholar 

  40. Landman, U., Ledwith, A., Marsh, D.G., and Williams, D.J., Macromolecules, 1976, vol. 9, no. 5, p. 833.

    Article  CAS  Google Scholar 

  41. Shudo, K., Kobayashi, T., and Utsunomiya, C., Tetrahedron, 1977, vol. 33, no. 14, p. 1721.

    Article  CAS  Google Scholar 

  42. Vokin, A.I. and Turchaninov, V.K., Izv. Akad. Nauk, Ser. Khim., 1995, no. 12, p. 2365.

    Google Scholar 

  43. Zweig, A., Lehnsen, J.E., and Murray, M.A., J. Am. Chem. Soc., 1963, vol. 85, no. 24, p. 3933.

    Article  CAS  Google Scholar 

  44. Rathore, R., Lindeman, S.V., and Kochi, J.K., J. Am. Chem. Soc., 1997, vol. 119, no. 40, p. 9393.

    Article  CAS  Google Scholar 

  45. von Meier, H., Heiss, J., Surh, H., and Müller, E., Tetrahedron, 1968, vol. 24, no. 5, p. 2307.

    Article  CAS  Google Scholar 

  46. Voigt, E.M., J. Am. Chem. Soc., 1964, vol. 86, no. 18, p. 3611.

    Article  CAS  Google Scholar 

  47. Foster, R., Organic Charge-Transfer Complexes, London: Academic, 1969.

    Google Scholar 

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Original Russian Text © B.S. Pryalkin, 2013, published in Zhurnal Obshchei Khimii, 2013, Vol. 83, No. 2, pp. 249–256.

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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

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