Issue

Vol. 32 No. 6 (2020): Vol 32 Issue 6

Copyright (c) 2020 AJC

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Binding of Methyl Viologen and its Radical to p-Sulfonatocalix[4]arene

https://doi.org/10.14233/ajchem.2020.22516
Muktar Shaikh
Department of Chemistry, Shri Anand College, Pathardi-414102, India
Jayshree K. Khedkar
Department of Chemistry, Shri Anand College, Pathardi-414102, India

Corresponding Author(s) : Muktar Shaikh

shaikh.muktar@rediffmail.com

Asian Journal of Chemistry, Vol. 32 No. 6 (2020): Vol 32 Issue 6

Abstract

Binding of N,N′-dimethyl-4,4′-bipyridinium (methyl viologen, MV2+) and its radical (MV+•) to novel p-sulfonatocalix[n]arene (CX[4]-S,) host has been investigated using the density functional theory (DFT). The hydrogen bonded interactions between α-, β- and -CH3 protons of methyl viologen with SO3− groups of CX[4]-S render stability to their complexes. In the lowest energy structures, one of the methyl groups of MV2+ was partially penetrated within the cavity of CX[4]-S host owing to C-H···O interactions with upper rim of host while the remaining methyl group excluded from the cavity. The radical MV+• revealed qualitatively similar binding patterns to CX[4]-S host as that of MV2+. Moreover, interaction energy of methyl viologen dication was predicted to be larger than that of the corresponding radical cation.

Keywords

Calixarene Viologens Density functional theory Molecular electron density topography Hydrogen bonding
Shaikh, M., & Khedkar, J. K. (2020). Binding of Methyl Viologen and its Radical to p-Sulfonatocalix[4]arene. Asian Journal of Chemistry, 32(6), 1297–1302. https://doi.org/10.14233/ajchem.2020.22516
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. C.D. Gutsche, Monographs in Supramolecular Chemistry: Calixarenes; The Royal Society of Chemistry: Cambridge, U.K., vol. 1. (1989).
  2. C.D. Gutsche and I. Alam, Tetrahedron, 44, 4689 (1988); https://doi.org/10.1016/S0040-4020(01)86171-8
  3. C.D. Gutsche, ed.: E. Weber, Host Guest Complex Chemistry Macrocycles: Synthesis, Structures and applications, Springer: Berlin (1985).
  4. C.D. Gutsche, Calixarenes Revisited, Monographs in Supramolecular Chemistry, The Royal Society of Chemistry: Cambridge, UK (1998).
  5. N. Douteau-Guével, A.W. Coleman, J.P. Morel and N. Morel-Desrosiers, J. Phys. Org. Chem., 11, 693 (1998); https://doi.org/10.1002/(SICI)1099-1395(1998100)11:10<693::AIDPOC18>3.0.CO;2-8
  6. O.I. Kalchenko, F. Perret, N. Morel-Desrosiers and A.W.A. Coleman, J. Chem. Soc. Perkin. Trans. II, 258 (2001); https://doi.org/10.1039/b005497f
  7. A. Dondoni and A. Marra, Chem. Rev., 110, 4949 (2010); https://doi.org/10.1021/cr100027b
  8. J. Vicens and V. Bohmer, Calixarenes: A Versatile Class of Macrocyclic Compounds. Kluwer Academic Publishers: Dordrecht, Boston (1991).
  9. S. Ikeda and S. Shinkai, Chem. Rev., 97, 1713 (1997); https://doi.org/10.1021/cr960385x
  10. V. Böhmer, Angew. Chem. Int. Ed. Engl., 34, 713 (1995); https://doi.org/10.1002/anie.199507131
  11. A. Suwattanamala, A.L. Magalhães and J.A.N.F. Gomes, J. Mol. Struct. THEOCHEM, 729, 83 (2005); https://doi.org/10.1016/j.theochem.2005.03.060
  12. N. Iki, F. Narumi, T. Fujimoto, N. Morohashi and S. Miyano, J. Chem. Soc. Perkin Trans. II, 2745 (1998); https://doi.org/10.1039/a803734e
  13. S. Seiji, A. Koji, T. Takayuki, A. Takashi and M. Osamu, J. Chem. Soc. Perkin Trans. II, 2297 (1987).
  14. H. Bakirci, A.L. Koner and W.M. Nau, J. Org. Chem., 70, 9960 (2005); https://doi.org/10.1021/jo051689z
  15. S. Shinkai, K. Araki, T. Matsuda, N. Nishiyama, H. Ikeda, I. Takasu and M. Iwamoto, J. Am. Chem. Soc., 112, 9053 (1990); https://doi.org/10.1021/ja00181a004
  16. G. Arena, A. Casnati, A. Contino, F.G. Gulino, D. Sciotto and R. Ungaro, J. Chem. Soc., Perkin Trans. II, 419 (2000); https://doi.org/10.1039/a909847j
  17. K. Wang, D.S. Guo, H.Q. Zhang, D. Li, X.L. Zheng and Y. Liu, J. Med. Chem., 52, 6402 (2009); https://doi.org/10.1021/jm900811z
  18. H. Weidel and M. Russo, Monatsh. Chem., 3, 850 (1882); https://doi.org/10.1007/BF01516855
  19. E.L. Clennan, Coord. Chem. Rev., 248, 477 (2004); https://doi.org/10.1016/j.ccr.2004.01.001
  20. C.L. Bird and A.T. Kuhn, Chem. Soc. Rev., 10, 49 (1981); https://doi.org/10.1039/cs9811000049
  21. L.A. Summers, The Bipyridinium Herbicides, Academic Press: New York (1980).
  22. D. Meisel, W.A. Mulac and M.S. Matheson, J. Phys. Chem., 85, 179 (1981); https://doi.org/10.1021/j150602a015
  23. P.M.S. Monk, The Viologens. Physicochemical Properties, Synthesis and Applications of the Salts of 4,4′-Bipyridine, John Wiley & Sons: Chichester, U.K. (1998).
  24. J.M. Lu, S.V. Rosokha and J.K. Kochi, J. Am. Chem. Soc., 125, 12161 (2003); https://doi.org/10.1021/ja0364928
  25. W. Ong and A.E. Kaifer, J. Org. Chem., 69, 1383 (2004); https://doi.org/10.1021/jo035030+
  26. K. Wang, S.-Y. Xing, X.-G. Wang and H.-X. Dou, Org. Biomol. Chem., 13, 5432 (2015); https://doi.org/10.1039/C5OB00053J
  27. D.S. Guo, L.H. Wang and Y. Liu, J. Org. Chem., 72, 7775 (2007); https://doi.org/10.1021/jo701304g
  28. P. Politzer, Chemical Applications of Atomic and Molecular Electrostatic Potentials, Plenum: NewYork (1981).
  29. G. Naray-Szabo and G.G. Ferenczy, Chem. Rev., 95, 829 (1995); https://doi.org/10.1021/cr00036a002
  30. S.R. Gadre, S.A. Kulkarni and I.H. Shrivastava, J. Chem. Phys., 96, 5253 (1992); https://doi.org/10.1063/1.462710
  31. S.R. Gadre and R.N. Shirsat, Electrostatics of Atoms and Molecules. Universities Press: Hyderabad, India (2000).
  32. A.D. Becke, J. Chem. Phys., 98, 5648 (1993); https://doi.org/10.1063/1.464913
  33. C. Lee, W. Yang and R.G. Parr, Phys. Rev. B Condens. Matter, 37, 785 (1988); https://doi.org/10.1103/PhysRevB.37.785
  34. Y. Zhao and D.G. Truhlar, Theor. Chem. Acc., 120, 215 (2008); https://doi.org/10.1007/s00214-007-0310-x
  35. M.J. Frisch et al., Gaussian 09, Gaussian Inc.: Wallingford (2009).
  36. P. Balanarayan and S.R. Gadre, J. Chem. Phys., 119, 5037 (2003); https://doi.org/10.1063/1.1597652
  37. A.C. Limaye and S.R. Gadre, Curr. Sci., 80, 1296 (2001).
  38. R.F.W. Bader, Atoms in Molecules: A Quantum Theory, Oxford University Press: Oxford, U.K. (1990).
  39. D.F. Matta and R.J. Boyd, The Quantum Theory of Atoms in Molecules, An Introduction to the Quantum Theory of Atoms in Molecules, WileyVCH: Weinheim, pp. 1-34 (2007).
  40. K. Wolinski, J.F. Hinton and P. Pulay, J. Am. Chem. Soc., 112, 8251 (1990); https://doi.org/10.1021/ja00179a005
  41. S. Miertuš, E. Scrocco and J. Tomasi, Chem. Phys., 55, 117 (1981); https://doi.org/10.1016/0301-0104(81)85090-2
  42. A. Bagno, F. Rastrelli and G. Saielli, J. Org. Chem., 72, 7373 (2007); https://doi.org/10.1021/jo071129v
Read More
Author biographies is not available.
Download
PDF
Statistic
Read Counter : 4 Download : 2