DOI QR코드

DOI QR Code

Charge Transfer Complexing Between Indole Derivatives and Methylviologen and Effects of Sodium Dodecyl Sulfate on It

  • Joon Woo Park (Department of Chemistry, College of Natural Sciences, Ewha Womans University) ;
  • Sung-Jin Kim (Department of Chemistry, College of Natural Sciences, Ewha Womans University)
  • Published : 1984.06.20

Abstract

The charge transfer complex formations between indole derivatives and methylviologen were investigated spectroscopically. In aqueous solutions near room temperature, the order of complex stability was tryptamine < tryptophan < indole < indole acetate, which is the reverse order of the magnitude of molar absorptivities. This was interpreted as involvement of contact charge transfer. The decrease of enthalpy of complex formation (-${\Delta}$H) was highest in tryptamine, and lowest in indole acetate. ${\Delta}$H and entropy of complex formation (${Delta}$S) varied nearly in a linear fashion with isokinetic temperature $242^{\circ}$K. These results were attributed to the hydration-dehydration properties of the side chains in indole derivatives. Except indole acetate, the complex formations were greatly enhanced by the addition of sodium dodecyl sulfate(SDS). However, the direct relationship between the enhanced complex formation and SDS micelle formation was not found. The enhanced charge transfer interaction inSDS solutions was attributed to the increased ${\Delta}$S by interaction between methylviologen and SDS in premicellar level. The order of complex stability in SDS solutions was indole acetate < tryptophan < trypamine < indole, which reflects the hydrophobicity of indole derivatives as well as electrostatic interaction between indole derivatives and methylviologen associated with SDS.

Keywords

References

  1. J. Amer. Chem. Soc. v.74 R. S. Mulliken
  2. J. Phys. Chem. v.85 F. M. Martens;J. W. Verhoeven
  3. Helv. Chim. Acta v.57 J. W. Verhoeven;A. M. Verhoeven-Schoff;A. M. Masson;R. Schwyzer
  4. Spectrochim. Acta v.38A A. S. N. Murthy;A. P. Bhardwaj
  5. The Bipyridinium Herbicides L. A. Summers
  6. J. Poly. Sci. v.20 M. Kaneko;M. Ochiai;K. Kinosita;A. Yamada
  7. J. Chem. Soc. Farad. Trens. I v.65 B. G. White
  8. Catalysis by Electron Donor-Acceptor Complexes: Their general behaviors and biologcal roles K. Tamaru;M. Ichikawa
  9. J. Amer. Chem. Soc. v.79 L. E. Orgel;M. S. Mulliken
  10. J. Amer. Chem. Soc. v.71 H. A. Benesi;J. H. Hildebrand
  11. Catalysis in Micellar and Macromolecular Systems J. H. Fendler;E. J. Fendler
  12. The Bipyridinium Herbicides L. A. Summers
  13. The Bipyridinium Herbicides L. A. Summers
  14. J. Kor. Chem. Soc. v.27 Y.-T. Park
  15. J. Amer. Chem. Soc. v.96 C. R. Bock;T. J. Meyer;D. G. Whitten
  16. Biochemistry v.9 R. A. Bradshaw;D. A. Deranleau
  17. J. Phys. Chem. v.86 J. H. Baxendale;M. A. J. Rodgers
  18. J. Biol. Chem. v.236 G. Cilento;P. Giusti
  19. J. Chem. Soc. Farad. Trans. I v.74 A. Cipiciani;S. Santini;G. Savelli
  20. J. Chem. Soc. Farad. Trens. I v.71 G. G. Aloisi;S. Santini;G. Savelli
  21. Bull. Chem. Soc. Jap. v.48 S. Shinkai;K. Tamaki;T. Kunitake
  22. J. Phys. Chem. v.79 T. Okubo;T. Ishiwatari;K. Mita;N. Ise
  23. J. Amer. Chem. Soc. v.96 L. M. Hinman;C. R. Coan;D. A. Deranleau
  24. J. Biol. Chem. v.247 F. M. Robbins;L. G. Holmes
  25. J. Phys. Chem. v.71 M. F. Emerson;A. Holtzer

Cited by

  1. Molecular Anion Binding and Substrate Photooxidation in Visible Light by 2,7-Diazapyrenium Cations vol.70, pp.1, 1984, https://doi.org/10.1002/hlca.19870700102
  2. Classical and non-classical melatonin receptor agonist-directed micellization of bipyridinium-based supramolecular amphiphiles in water vol.16, pp.20, 1984, https://doi.org/10.1039/d0sm00424c