Skip to main content
SpringerLink
Log in

Interaction of atenolol with iodine: a novel structural formula of charge transfer complexes

  • Original Paper
  • Published:
Journal of the Iranian Chemical Society Aims and scope Submit manuscript

Abstract

Interaction of atenolol (ATE), as an electron donor, with iodine (I2), as a typical σ-electron acceptor, has been studied. This interaction occurs in several remarkable steps. The first step is the initial formation of the ATE–I2 outer charge transfer (CT) complex, meanwhile this interaction ends with the formation of the solid CT complex which has the stoichiometric ratio 4:2 (ATE:I2). The synthesized solid CT complex has a novel and amazing structural formula in which hydrogen bonds exist side by side with the CT binding. Formation constants, molar absorption coefficients, and thermodynamic properties, ΔH, ΔS, and ΔG, of this ATE/I2 interaction have been determined and discussed. The different structural forms of the ATE/I2 complexes which occur in each of the different formation steps, involving their stoichiometric ratios, have been determined and confirmed. Several techniques involving UV/Visible, FT-IR, 1H NMR, and Mass spectra have been used in this study. In addition, morphology of the synthesized solid complex has been investigated by the scanning electron microscope.

Graphical Abstract

The charge transfer (CT) interaction between atenolol (ATE) and iodine (I2) occurs in several remarkable steps starting with an initial formation of the ATE–I2 outer CT complex and ending by formation of the solid CT complex having the stoichiometric ratio 4:2 (ATE:I2). The synthesized solid CT complex has a novel and amazing structural formula in which hydrogen bonds exist side by side with the CT binding. Several techniques involving UV/Visible, FT-IR, 1H NMR, and Mass spectra have been used in this study. In addition, morphology of the synthesized solid complex has been investigated by the scanning electron microscope (SEM).

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. U.M. Rabie, M.H. Abou-El-Wafa, H. Nassar, Spectrochim. Acta 78A, 512 (2011)

    CAS  Google Scholar 

  2. U.M. Rabie, M.H. Abou-El-Wafa, H. Nassar, Spectrochim. Acta 79A, 1411 (2011)

    Google Scholar 

  3. U.M. Rabie, M.H. Abou-El-Wafa, H. Nassar, Spectrochim. Acta 86A, 252 (2011)

    Google Scholar 

  4. R.A.E. de Castro, J. Canotilho, R.M. Barbosa, J.S. Redinha, Spectrochim. Acta 67A, 1194 (2007)

    Google Scholar 

  5. G.S. Schneider, J. Emerg. Med. 38, e49 (2010)

    Article  Google Scholar 

  6. E. Moltzer, F.U.R. Mattace, Y. Karamermer, E. Boersma, G.D. Webb, M.L. Simoons, A.H. Danser, A.H. van den Meiracker, J.W. Roos-Hesselink, Am. J. Cardiol. 105, 217 (2010)

    Article  CAS  Google Scholar 

  7. I. Kikic, P. Alessi, F. Eva, M. Moneghini, B. Perissutti, J. Supercrit. Fluids 38, 434 (2006)

    Article  CAS  Google Scholar 

  8. O. Cozar, L. Szabó, I.B. Cozar, N. Leopold, L. David, C. Cãinap, V. Chiş, J. Mol. Struct. 993, 357 (2011)

    Article  CAS  Google Scholar 

  9. S. Pruneanu, F. Pogacean, C. Grosan, E.M. Pica, L.C. Bolundut, A.S. Biris, Chem. Phys. Lett. 504, 56 (2011)

    Article  CAS  Google Scholar 

  10. R.N. Goyal, V.K. Gupta, M. Oyama, N. Bachheti, Electrochem. Commun. 8, 65 (2006)

    Article  CAS  Google Scholar 

  11. R.N. Goyal, S.P. Singh, Talanta 69, 932 (2006)

    Article  CAS  Google Scholar 

  12. M. Behpour, E. Honarmand, S.M. Ghoreishi, Bull. Korean Chem. Soc. 31, 845 (2010)

    Article  CAS  Google Scholar 

  13. M.A. Gotardo, R. Sequinel, L. Pezza, H.R. Pezza, Ecl. Quím., São Paulo 33, 7 (2008)

    Article  Google Scholar 

  14. M. Arvand, M. Vaziri, M. Vejdani, Mater. Sci. Eng. C30, 709 (2010)

    Google Scholar 

  15. H. Salem, J. Pharm. Biomed. Anal. 29, 527 (2002)

    Article  CAS  Google Scholar 

  16. M. Pandeeswaran, K.P. Elango, Int. J. Chem. Kinet. 40, 559 (2008)

    Article  CAS  Google Scholar 

  17. M. Pandeeswaran, K.P. Elango. J. Solut. Chem. 38, 1558 (2009)

    Article  CAS  Google Scholar 

  18. H.A. Benesi, J.H. Hildebrand, J. Am. Chem. Soc. 71, 2703 (1949)

    Article  CAS  Google Scholar 

  19. R.L. Scott, Recl. Trav. Chim. Pays-Bas 75, 787 (1956)

    Article  CAS  Google Scholar 

  20. G.N. Lewis, M. Randall, Thermodynamics, 2nd Edn. (revised by K.S. Pitzed, L. Brewer) (McGraw-Hill, New York, 1961)

  21. R.S. Mulliken, J. Am. Chem. Soc. 74, 811 (1952)

    Article  CAS  Google Scholar 

  22. R.S. Mulliken, J. Phys. Chem. 56, 801 (1952)

    Article  CAS  Google Scholar 

  23. R.S. Mulliken, Recl. Trav. Chim. Pays-Bas 57, 845 (1956)

    Google Scholar 

  24. R.S. Mulliken, W.B. Pearson, Molecular Complexes—A Lecture and Reprint Volume (Wiley Interscience, New York, 1969)

    Google Scholar 

  25. V.G. Krishna, M. Chowdhury, J. Phys. Chem. 67, 1067 (1963)

    Article  CAS  Google Scholar 

  26. G.G. Aloisi, S. Pignataro, J. Chem. Soc., Faraday Trans.1 69, 534 (1973)

    Article  CAS  Google Scholar 

  27. D.R. Lide, Handbook of Chemistry and Physics, 77th edn. (CRC Press, Boca Raton, 1996)

    Google Scholar 

  28. P. Job, Ann. Chem. Phys. 2, 113 (1928)

    Google Scholar 

  29. H.M.A. Salman, M.R. Mahmoud, M.H.M. Abou-El-Wafa, U.M. Rabie, R.H. Crabtree, Inorg. Chem. Commun. 7, 1209 (2004)

    Article  CAS  Google Scholar 

  30. I. Uruska, Spectrochim. Acta 36A, 639 (1980)

    CAS  Google Scholar 

  31. R. Abu-Eittah, M.M. Hamed, Can. J. Chem. 57, 2337 (1979)

    Article  CAS  Google Scholar 

  32. H.M.A. Salman, U.M. Rabie, E.M. Abd-Alla, Can. J. Anal. Sci. Spectrosc. 49, 1 (2004)

    CAS  Google Scholar 

  33. R. Abdel-Hamid, A.A. El-Samahy, A.H. El-Taher, H. El-Sagher, Can. J. Chem. 65, 468 (1987)

    Article  CAS  Google Scholar 

  34. R.S. Becker, A.B.F. Duncan, F.A. Masten, D.R. Scott, W. West, Chemical Applications of Spectroscopy (Wiley, New York, 1968)

    Google Scholar 

  35. U.M. Rabie, R.A. Mohamed, M.H.M. Abou-El-Wafa, Spectrochim. Acta 68A, 605 (2007)

    CAS  Google Scholar 

  36. E.M. Kosower, J. Org. Chem. 20, 956 (1964)

    Article  Google Scholar 

  37. E. Le Goff, R.B. LaCount, J. Am. Chem. Soc. 85, 1354 (1963)

    Article  Google Scholar 

  38. P.M. Echenique, R. Berndt, E.V. Chulkov, T. Fauster, A. Goldmann, U. Höfer, Surf. Sci. Rep. 54, 219 (2004)

    Article  Google Scholar 

  39. A. Föhlisch, P. Feulner, F. Hennies, A. Fink, D. Menzel, A. Sanchez-Portal, P.M. Echenique, W. Wurth, Nature 436, 373 (2005)

    Article  Google Scholar 

  40. A. Föhlisch, S. Vijayalakshmi, A. Pietzsch, M. Nagasono, W. Wurth, P.S. Kirchmann, P.A. Loukakos, U. Bovensiepen, M. Wolf, M. Tchaplyguine, F. Hennies, Surf. Sci. 606, 881 (2012)

    Article  Google Scholar 

  41. E.M. Nour, L.H. Chen, J. Laane, J. Phys. Chem. 90, 2841 (1986)

    Article  CAS  Google Scholar 

  42. R. Foster, Organic Charge-Transfer Complexes (Academic Press, London, 1969)

    Google Scholar 

  43. S.N. Bhat, C.N.R. Rao, J. Am. Chem. Soc. 88, 3216 (1966)

    Article  CAS  Google Scholar 

  44. M.M.A. Hamed, E.M. Abdalla, M.R. Mahmoud, Can. J. Appl. Spectrosc. 39, 24 (1994)

    CAS  Google Scholar 

  45. N.S. Rao, G.B. Rao, D. Ziessow, Spectrochim. Acta 46A, 1107 (1990)

    CAS  Google Scholar 

  46. M. Hasani, M. Shamsipur, J. Inclusion Phenom, Macromol. Chem. 48, 135 (2004)

    CAS  Google Scholar 

  47. U.M. Rabie, J. Mol. Struct., Accepted. doi:10.1016/j.molstruc.2012.08.032, and references therein

  48. H. Liu, Q. Zhao, Y. Li, Y. Liu, F. Lu, J. Zhuang, S. Wang, L. Jiang, D. Zhu, D. Yu, L. Chi, J. Am. Chem. Soc. 127, 1120 (2005)

    Article  CAS  Google Scholar 

  49. S. Cui, H. Liu, L. Gan, Y. Li, D. Zhu, Adv. Mater. 20, 2918 (2008)

    Article  CAS  Google Scholar 

  50. L. Yang, C. Guan, W. Yue, J.Y. Wu, H. Yan, X. Zhang, Z. Wang, X. Zhan, Y. Li, D. Wang, Acc. Chem. Res. 43, 1496 (2010)

    Article  Google Scholar 

  51. H. Zheng, Yo Li, H. Liu, X. Yin, Y. Li, Chem. Soc. Rev. 40, 4506 (2011)

    Article  CAS  Google Scholar 

  52. R.A.E. de Castro, J. Canotilho, R.M. Barbosa, M.R. Silva, A.M. Beja, J.A. Paixao, J.S. Redinha, Cryst. Growth Des. 7, 496 (2007)

    Article  Google Scholar 

  53. O. Cozar, V. Chiş, L. David, M. Baias, J. Optoelectron. Adv. Mater. 8, 164 (2006)

    CAS  Google Scholar 

  54. M. Picquart, L. Grajcar, M.H. Baron, Z. Abedinzadeh, Biospectroscopy 5, 328 (1999)

    Article  CAS  Google Scholar 

  55. D.L. Pavia, G.M. Lampman, G.S. Kriz, Introduction to Spectroscopy, 3rd edn. (Harcourt College, Orlando, 2001)

    Google Scholar 

  56. Th Emmler, S. Gieschler, H.H. Limbach, G. Buntkowsky, J. Mol. Struct. 700, 29 (2004)

    Article  CAS  Google Scholar 

  57. J.B. Lambert, H.F. Shurvell, D.A. Lightner, R.G. Cooks, Introduction to Organic Spectroscopy (Macmillan Publishing Company, New York, 1987)

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Chemistry Department, Faculty of Science at Qena, South Valley University, Qena, 83523, Egypt

    Usama M. Rabie, Moustafa H. Abou-El-Wafa & Ramadan A. Mohamed

Authors
  1. Usama M. Rabie
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Moustafa H. Abou-El-Wafa
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ramadan A. Mohamed
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Usama M. Rabie.

Electronic supplementary material

Rights and permissions

Reprints and permissions

About this article

Cite this article

Rabie, U.M., Abou-El-Wafa, M.H. & Mohamed, R.A. Interaction of atenolol with iodine: a novel structural formula of charge transfer complexes. J IRAN CHEM SOC 10, 889–896 (2013). https://doi.org/10.1007/s13738-013-0225-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-013-0225-5

Keywords

Search

Navigation