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Charge-transfer absorption of olefins with nitrosonium. Structural relevance to the dimethylbutene complex with dinitrogen tetraoxide

Abstract

The transient electron donor-acceptor (EDA) complexes of various olefins (dimethylbutene, etc.) with the nitrosonium acceptor (NO+) show diagnostic charge-transfer absorption bands in dichloromethane solutions at low temperatures. Since the same charge-transfer absorption bands are observed when olefins are exposed to dinitrogen tetraoxide, they are ascribed to analogous EDA complexes [olefin, NO+] NO3 that are derived from the ionic disproportionation of nitrogen dioxide.

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References

  1. H. Shechter, Rec. Chem. Prog. 25, 55 (1964). b) H.O. Larson. In: The Chemistry of the Nitro and Nitroso Groups, H. Feuer (Ed.), Interscience, New York, 1969, pp. 319 ff.

    CAS  Google Scholar 

  2. W.A. Pryor, J.W. Lightsey, and D.F. Church, J. Am. Chem. Soc. 104, 6685 (1982). b) D.H. Giamalva, G.B. Kenion, D.F. Church, and W.A. Pryor, J. Am. Chem. Soc. 109, 7059 (1987).

    Article  CAS  Google Scholar 

  3. J. Chatterjee, R.G. Coombes, J.R. Barnes, and M.J. Fildes, J. Chem. Soc., Perkin Trans. 1, 1031 (1995).

    Google Scholar 

  4. T.F. Redmond and B.B. Wayland, J. Phys. Chem. 72, 1626 (1968). b) D.W. James and R.C. Marshall, J. Phys. Chem. 72, 2963 (1968). c) J. Brunning, M.J. Frost, and I.W.M. Smith, Int. J. Chem. Kinet. 20, 957 (1988). d) A.J. Vosper, J. Chem. Soc. (A), 2191 (1970).

    Article  CAS  Google Scholar 

  5. See Pryor et al. in Ref 2..

    Article  CAS  Google Scholar 

  6. E.F. Schoenbrunn and J.H. Gardner, J. Am. Chem. Soc. 82, 4905 (1960). b) B.T. Ustavshchikov, V.A. Podgornova, N.V. Dormidontova, and M.I. Farberov, Dokl. Akad. Nauk SSSR 157, 143 (1964).

    Article  CAS  Google Scholar 

  7. J.B. Wilkes and R.G. Wall, J. Org. Chem. 45, 247 (1980).

    Article  CAS  Google Scholar 

  8. L. Parts and J.T. Miller, Jr. J. Phys. Chem. 73, 3088 (1969).

    Article  CAS  Google Scholar 

  9. L. Parts and J.T. Miller, Jr. J. Chem. Phys. 43, 136 (1965).

    Article  CAS  Google Scholar 

  10. A. Givan and A. Loewenschuss, J. Chem. Phys. 94, 7562 (1991).

    Article  CAS  Google Scholar 

  11. M. Nakata and H. Frei, J. Phys. Chem. 93, 7670 (1989). b) M. Nakata and H. Frei, J. Am. Chem. Soc. 111, 5240 (1989). c) M. Nakata, K. Shibuya, and H. Frei, J. Phys. Chem. 94, 8168 (1990).

    Article  CAS  Google Scholar 

  12. D.J. Fitzmaurice and H. Frei, J. Phys. Chem. 95, 2652 (1991). b) M. Nakata and H. Frei, J. Am. Chem. Soc. 114, 1363 (1992). c) D.J. Fitzmaurice and H. Frei, J. Phys. Chem. 96, 10308 (1992). See also: H. Frei, Chimia 45, 175 (1991). d) M. Nakata, Spectrochim. Acta 50A, 1455 (1994). e) J.C. Loison, C. Dedonder-Lardeux, C. Jouvet, and D. Solgadi, J. Phys. Chem. 95, 9192 (1991).

    Article  CAS  Google Scholar 

  13. F. Blatter and H. Frei, J. Phys. Chem. 97, 1178 (1993).

    Article  CAS  Google Scholar 

  14. E. Bosch and J.K. Kochi, Res. Chem. Intermed. 19, 811 (1993).

    Article  CAS  Google Scholar 

  15. M.L. Scheinbaum and M.B. Dines, Tetrahedron Lett. 2205 (1971). b) G.H. Lee, J.M. Lee, W.B. Jeong, and K. Kim, Tetrahedron Lett. 29, 4437 (1988). c) G.A. Olah, P. Schilling, P.W. Westerman, and H.C. Lin, J. Am. Chem. Soc. 96, 3581 (1974).

  16. E. Iglesias, L. Garcia-Rio, J.R. Leis, M.E. Pena, and D.L.H. Williams, J. Chem. Soc. Perkin Trans. 2, 1673 (1992).

    Google Scholar 

  17. For the generation of NO+ from octyl nitrite with trifluoroacetic acid, see Iglesias et al. in Ref. 16..

    Google Scholar 

  18. Y. Tapuhi and E. Grushka. In: The Chemistry of Amino, Nitroso and Nitro Compounds and their Derivatives, S. Patai (Ed.), Wiley, New York, 1982, Supplement F, Part 2, p. 909.

    Google Scholar 

  19. D.I. Makhonkov, A.V. Cheprakov, M.A. Rodkin, and I.P. Beletskaya, Zh. Org. Khim. 24, 241 (1988).

    CAS  Google Scholar 

  20. S. Brownstein, E. Gabe, F. Lee, and L. Tan, J. Chem. Soc., Chem. Commun. 1567 (1984). b) S. Brownstein, E. Gabe, F. Lee, and A. Piotrowski, Can. J. Chem. 64, 1661 (1986).

  21. E. Bosch and J.K. Kochi, J. Org. Chem. 59, 3314 (1994).

    Article  CAS  Google Scholar 

  22. R. Foster, Organic Change-Transfer Complexes, Academic, New York, 1969.

    Google Scholar 

  23. E.K. Kim and J.K. Kochi, J. Am. Chem. Soc. 113, 4962 (1991).

    Article  CAS  Google Scholar 

  24. R.M. Minyaev, M.E. Kletskii, and V.I. Minkin, Zh. Org. Khim. 23, 2508 (1987).

    CAS  Google Scholar 

  25. S.G. Lias, Chem. Phys. Lett. 54, 147 (1978).

    Article  CAS  Google Scholar 

  26. E. Bosch and J.K. Kochi, J. Org. Chem. 60, 3172 (1995). b) S. Ricard, P. Audet, and R. Savoie, J. Molec. Struct. 178, 135 (1988).

    Article  CAS  Google Scholar 

  27. M. Tsuchiya, R. Akaba, S. Aihara, H. Sakuragi, and K. Tokumaru, Chem. Lett. 1727 (1986).

  28. R.S. Mulliken, J. Am. Chem. Soc. 72, 600 (1950). b) R.S. Mulliken and W.B. Person, Molecular Complexes, Wiley, New York, 1969.

    Article  CAS  Google Scholar 

  29. M.W. Hanna and J.L. Lippert, In: Molecular Complexes, Vol. 1, R. Foster (Ed.), Crane Russak, New York, 1973, p. 2 ff.

    Google Scholar 

  30. T.M. Bockman, Z. Karpinski, S. Sankararaman, and J.K. Kochi, J. Am. Chem. Soc. 114, 1970 (1992).

    Article  CAS  Google Scholar 

  31. E. Bosch and J.K. Kochi, submitted for publication. See also M. Nakata, in Ref. 12 d).

    Google Scholar 

  32. K.Y. Lee and J.K. Kochi, J. Chem. Soc., Perkin Trans. 2, 237 (1994).

    Google Scholar 

  33. C.C. Addison and D. Sutton, Prog. Inorg. Chem. 8, 195 (1967). b) C.C. Addison, Chemistry in Liquid Dinitrogen Tetroxide, Vieweg, Braunschweig, 1967.

    Article  CAS  Google Scholar 

  34. W.A. Noyes, Org. Syntheses Coll. Vol. 2, 2, 108 (1961).

    Google Scholar 

  35. J.R. Morton and H.W. Wilcox, Inorg. Synth. 4, 48 (1953).

    Article  CAS  Google Scholar 

  36. E.W. Meijer and H. Wynberg, J. Chem. Ed. 59, 1071, (1982).

    Article  CAS  Google Scholar 

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Bosch, E., Kochi, J.K. Charge-transfer absorption of olefins with nitrosonium. Structural relevance to the dimethylbutene complex with dinitrogen tetraoxide. Res. Chem. Intermed. 22, 209–224 (1996). https://doi.org/10.1163/156856796X00412

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  • DOI: https://doi.org/10.1163/156856796X00412

Keywords

  • Nitrogen Dioxide
  • Nitrosonium
  • Dimethylbutene
  • Nitrosyl Chloride
  • Antimony Pentachloride