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Cooperativity of CH/π and hydrogen bond interactions in HF···Py⊥X1benX2 complexes

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Abstract

A cooperativity is observed between CH/π and hydrogen bond interactions in HF···Py⊥X1benX2 complexes. The cooperativity is more influenced by the inductive effects in comparison with the resonance effects. Increase in the electron withdrawing nature of substituents is accompanied by decrease in the cooperativity energy (E coop). The vital effect of the reactivity centre on the E coop is determined through the good relationship between σ +para (the substituted constant estimated for the para placed reactivity center) and E coop values.

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References

  1. C.A. Hunter, K.R. Lawson, J. Perkins, C.J. Urch, J. Chem. Soc. Perkin. Trans. 2 2, 651 (2001)

    Article  Google Scholar 

  2. E.A. Meyer, R.K. Castellano, F. Diederich, Angew. Chem. Int. Ed. 42, 1210 (2003)

    Article  CAS  Google Scholar 

  3. J.C. Ma, D.A. Dougherty, Chem. Rev. 97, 1303 (1997)

    Article  CAS  Google Scholar 

  4. S.K. Burley, G.A. Petsko, Science 229, 23 (1985)

    Article  CAS  Google Scholar 

  5. J. Singh, J.M. Thornton, FEBS Lett. 191, 1 (1985)

    Article  CAS  Google Scholar 

  6. C.A. Hunter, J.K.M.J. Sanders, Am. Chem. Soc. 112, 5525 (1990)

    Article  CAS  Google Scholar 

  7. J.N.H. Reek, A.H. Priem, H. Engelkamp, A.E. Rowan, J.A.A.W. Elemans, R.J.M.J. Nolte, Am. Chem. Soc. 119, 9956 (1997)

    Article  CAS  Google Scholar 

  8. D. Ranganathan, V. Haridas, R. Gilardi, I.L.J. Karle, Am. Chem. Soc. 120, 10793 (1998)

    Article  CAS  Google Scholar 

  9. M. Asakawa, P.R. Ashton, W. Hayes, H.M. Janssen, E.W. Meijer, S. Menzer, D. Pasini, J.F. Stoddart, A.J.P. White, D.J.J. Williams, Am. Chem. Soc. 120, 920 (1998)

    Article  CAS  Google Scholar 

  10. D.B. Amabilino, P.R. Ashton, V. Balzani, S.E. Boyd, A. Credi, J.Y. Lee, S. Menzer, J.F. Stoddart, M. Venturi, D.J.J. Williams, Am. Chem. Soc. 120, 4295 (1998)

    Article  CAS  Google Scholar 

  11. M. Teale, J. Symersky, L. DeLucas, Bioconj. Chem. 13, 403 (2002)

    Article  CAS  Google Scholar 

  12. A.Y. Lau, M.D. Wyatt, B.J. Glassner, L.D. Samson, T. Ellenberger, Proc. Natl. Acad. Sci. 97, 13573 (2000)

    Article  CAS  Google Scholar 

  13. L.R. Rutledge, S.D.J. Wetmore, Chem. Theory Comput. 4, 1768 (2008)

    Article  CAS  Google Scholar 

  14. P. Mignon, S. Loverix, F. De Proft, P.J. Geerlings, Phys. Chem. A 108, 6039 (2004)

    Article  Google Scholar 

  15. L. Mao, Y. Wang, Y. Liu, X.J. Hu, Mol. Biol. 336, 787 (2004)

    Article  CAS  Google Scholar 

  16. A. Vazquez-Mayagoitia, C.D. Sherrill, E. Apra, B.G.J. Sumpter, Chem. Theory Comput. 6, 727 (2010)

    Article  CAS  Google Scholar 

  17. M. Piacenza, S. Grimme, Chem. Phys. Chem. 6, 1554 (2005)

    Article  CAS  Google Scholar 

  18. L.R. Ashley, M.S. Figgs, M.O. Sinnokrot, C.D.J. Sherrill, Phys. Chem. A 110, 10822 (2006)

    Article  Google Scholar 

  19. C. Hansch, A. Leo, R.W. Taft, Chem. Rev. 91, 165 (1991)

    Article  CAS  Google Scholar 

  20. L.P. Hammett, Chem. Rev. 17, 125 (1935)

    Article  CAS  Google Scholar 

  21. E.C. Lee, B.H. Hong, J.Y. Lee, J.C. Kim, D. Kim, Y. Kim, P. Tarakeshwar, K.S.J. Kim, Am. Chem. Soc. 127, 4530 (2005)

    Article  CAS  Google Scholar 

  22. P.J. Berti, J.A.B. McCann, Chem. Rev. 106, 506 (2006)

    Article  CAS  Google Scholar 

  23. A. Ebrahimi, M. Habibi, R.S. Neyband, A.R. Gholipour, Phys. Chem. Chem. Phys. 11, 11424 (2009)

    Article  CAS  Google Scholar 

  24. M.N. Ali Mohamed, H.D. Watts, J. Guo, J.M. Catchmark, J.D. Kubicki, Carbohydr. Res. 345, 1741 (2010)

    Article  Google Scholar 

  25. Y. Umezawa, M. Nishio, Bioorg. Med. Chem. 6, 493 (1998)

    Article  CAS  Google Scholar 

  26. Y. Umezawa, M. Nishio, Bioorg. Med. Chem. 8, 2643 (2000)

    Article  CAS  Google Scholar 

  27. Y. Umezawa, S. Tsuboyama, H. Takahashi, J. Uzawa, M. Nishio, Bioorg. Med. Chem. 7, 2021 (1999)

    Article  CAS  Google Scholar 

  28. A. Scrivanti, F. Benetollo, A. Venzo, M. Bertoldini, V. Beghetto, U.J. Matteoli, Organomet. Chem. 692, 3577 (2007)

    Article  CAS  Google Scholar 

  29. M.K. Paira, J. Dinda, T.-H. Lu, A.R. Paital, C. Sinha, Polyhedron 26, 4131 (2007)

    Article  CAS  Google Scholar 

  30. A.M. Santana, J.G. Ferreira, A.C. Moro, S.C. Lemos, A.E. Mauro, A.V.G. Netto, R.C.G. Frem, R.H.A. Santos, Inorg. Chem. Commun. 14, 83 (2011)

    Article  CAS  Google Scholar 

  31. T. Ozawa, E. Tsuji, M. Ozawa, C. Handa, H. Mukaiyama, T. Nishimura, S. Kobayashi, K. Okazaki, Bioorg. Med. Chem. 16, 10311 (2008)

    Article  CAS  Google Scholar 

  32. R. Zhao, S. Matsumoto, M. Akazome, K. Ogura, Tetrahedron 58, 10233 (2002)

    Article  CAS  Google Scholar 

  33. M.J. Palusiak, Organomet. Chem. 692, 3866 (2007)

    Article  CAS  Google Scholar 

  34. C. Møller, M.S. Plesset, Phys. Rev. 46, 618 (1934)

    Article  Google Scholar 

  35. M. Head-Gordon, J.A. Pople, M.J. Frisch, Chem. Phys. Lett. 153, 503 (1988)

    Article  CAS  Google Scholar 

  36. M.J. Frisch et al., GAUSSIAN03 (Revision B.03) (Gaussian Inc, Pittsburgh, 2003)

  37. S.B. Boys, F. Bernardi, Mol. Phys. 19, 553 (1970)

    Article  CAS  Google Scholar 

  38. F.W. Biegler König, J. Schönbohm, D.J. Bayles, Comput. Chem. 22, 545 (2001)

    Article  Google Scholar 

  39. C.M. Breneman, K.B.J. Wiberg, Comput. Chem. 11, 361 (1990)

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, University of Sistan and Baluchestan, P.O. Box 98135-674, Zahedan, Iran

    Pouya Karimi, Ali Ebrahimi & Sophia Bazzi

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  1. Pouya Karimi
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  2. Ali Ebrahimi
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  3. Sophia Bazzi
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Correspondence to Sophia Bazzi.

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Karimi, P., Ebrahimi, A. & Bazzi, S. Cooperativity of CH/π and hydrogen bond interactions in HF···Py⊥X1benX2 complexes. J IRAN CHEM SOC 9, 991–998 (2012). https://doi.org/10.1007/s13738-012-0117-0

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  • DOI: https://doi.org/10.1007/s13738-012-0117-0

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