Solvent effect on acid–base clustering between acetic acid and pyridine

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Yoshikatsu Akiyama, Akihiro Wakisaka, Fujio Mizukami and Kengo Sakaguchi


Abstract

The solvent effect on the acid–base interaction between acetic acid and pyridine has been studied by the mass spectrometric analysis of clusters isolated from liquid droplets. The clusters resulting from the acetic acid–pyridine, acid–base, interaction in water are quite different from those in acetonitrile solvent. In water (acetic acid∶pyridine∶water = 1∶1∶10) the acid–base interaction occurs through the intercluster interaction between acetic acid and pyridine clusters. On the other hand, in acetonitrile (acetic acid∶pyridine∶acetonitrile = 1∶1∶10), the acid–base interaction proceeds through an intermonomer interaction between an acetic acid molecule and pyridine molecule, and the clusters are produced through the aggregation of a polar (acetic acid)δ–(pyridine)δ+ complex. This solvent effect is mainly attributed to the cluster structure of acetic acid and pyridine in water and acetonitrile solvent.


References

  1. A. Wakisaka, S. Takahashi and N. Nishi, J. Chem. Soc., Faraday Trans., 1995, 91, 4063 RSC.
  2. (a) A. Wakisaka, Y. Akiyama, Y. Yamamoto, T. Engst, H. Takeo, F. Mizukami, K. Sakaguchi and H. Jones, J. Chem. Soc., Faraday Trans., 1996, 92, 3539 RSC; (b) A. Wakisaka, Y. Yamamoto, Y. Akiyama, F. Mizukami and K. Sakaguchi, J. Chem. Soc., Faraday Trans., 1996, 92, 3339 RSC; (c) T. Arai, T. Koyama and A. Wakisaka, Chem. Lett., 1997, 123 CrossRef CAS.
  3. Z. Dega-Szafran and E. Dulewicz, J. Chem. Soc., Perkin Trans. 2, 1983, 345 RSC.
  4. Z. Dega-Szafran, M. Grundwaid-Xyspianska and M. Szafran, J. Chem. Soc., Faraday Trans., 1991, 87, 3825 RSC.
  5. P. Barczynski, Z. Dega-Szafran and M. Szafran, J. Chem. Soc., Perkin Trans. 2, 1987, 901 RSC.
  6. R. Kramer and G. Zundel, J. Chem. Soc., Faraday Trans., 1990, 86, 301 RSC.
  7. M. Iiczyszyn and H. Ratajczak, J. Chem. Soc., Faraday Trans., 1995, 91, 1611 RSC.
  8. T. Ikenoue and N. Yoshida, J. Phys. Chem., 1987, 91, 6440 CrossRef CAS.
  9. T. Ikenoue and N. Yoshida, J. Phys. Chem., 1988, 92, 4883 CrossRef CAS.
  10. N. Yoshida, J. Phys. Chem., 1990, 94, 6536 CrossRef CAS.
  11. N. S. Golubev, S. N. Smirnov, V. A. Gindin, G. S. Denisov, H. Benedict and H. Limbach, J. Am. Chem. Soc., 1994, 116, 12 055 CrossRef CAS.
  12. K. Yamamoto and N. Nishi, J. Am. Chem. Soc., 1990, 12, 549 CrossRef.
  13. M. Tsuchiya, S. Teshima, T. Kaneko and T. Hirano, J. Chem. Soc. Jpn., Chem. Ind. Chem., 1993, 6, 687.
  14. N. Nishi and K. Yamamoto, J. Am. Chem. Soc., 1987, 109, 7353 CrossRef CAS.
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