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Theoretical approach to the molecular structure, chemical reactivity, molecular orbital analysis, spectroscopic properties (IR, UV, NMR), and NBO analysis of deferiprone

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Abstract

In this investigation, the structural, electronic properties, 13C and 1H NMR parameters and the first hyperpolarizability of deferiprone are computed in the gas phase and various solvents at the M062X/6-311++G(d,p) level of theory. The solvent effect on the structural parameters, frontier orbital energies, 13C and 1H NMR parameters is also explored based on a polarizable continuum model. These consequences specify that the polarity of solvents affects the structures and spectroscopic properties of deferiprone. 1H and 13C NMR chemical shifts are evaluated by employing the gauge-invariant atomic orbital method. NBO analysis is exploited to examine the hybridization of atoms, atomic charges, and their second order stabilization energy within the molecule.

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References

  1. N. Sattarahmady, H. Heli, A. Moosavi-Movahedi, and K. Karimian, Mol. Biol. Rep., 41, 1723 (2014)

    Article  CAS  Google Scholar 

  2. N. F. Olivieri, G. M. Brittenham, C. E. McLaren, D. M. Templeton, R. G. Cameron, R. A. McClelland, A. D. Burt, and K. A. Fleming, New Eng. J. Med., 339, 417 (1998)

    Article  CAS  Google Scholar 

  3. M. T. Fosburg and D. G. Nathan, Blood, 76, 435 (1990)

    CAS  Google Scholar 

  4. d)N. F. Olivieri, G. M. Brittenham, D. Matsui, M. Berkovitch, L. M. Blendis, R. G. Cameron, R. A. McClelland, P. P. Liu, D. M. Templeton, and G. Koren, New Eng. J. Med., 332, 918 (1995).

    Article  CAS  Google Scholar 

  5. a)M. S. Dorraji, V. P. Azar, and M. Rasoulifard, Eur. J. Pharm. Sci., 64, 9 (2014)

    Article  Google Scholar 

  6. b)D. Song, L. Zhao, Y. Li, M. Hadziahmetovic, Y. Song, and J. L. Dunaief, Invest. Ophthalmol. Visual Sci., 55, 415 (2014)

    Google Scholar 

  7. c)D. Song, L. Zhao, Y. Li, M. Hadziahmetovic, Y. Song, J. Connelly, M. Spino, and J. L. Dunaief, Invest. Ophthalmol. Visual Sci., 55, 4525 (2014).

    Article  CAS  Google Scholar 

  8. a)P. Harmatz, E. Butensky, K. Quirolo, R. Williams, L. Ferrell, T. Moyer, D. Golden, L. Neumayr, and E. Vichinsky, Blood, 96, 76 (2000)

    CAS  Google Scholar 

  9. b)M. A. Engle, M. Erlandson, and C. H. Smith, Circulation, 30, 698 (1964)

    Article  CAS  Google Scholar 

  10. c)A. Cohen, Hematol. Oncol. Clin. N. Am., 1, 521 (1987).

    CAS  Google Scholar 

  11. a)B. Modell, M. Khan, and M. Darlison, The Lancet., 355, 2051 (2000)

    Article  CAS  Google Scholar 

  12. b)C. Borgna-Pignatti, S. Rugolotto, P. De Stefano, H. Zhao, M. D. Cappellini, G. C. Del Vecchio, M. A. Romeo, G. L. Forni, M. R. Gamberini, and R. Ghilardi, Haematologica, 89, 1187 (2004).

    Google Scholar 

  13. a)G. J. Kontoghiorghes, Hemoglobin, 30, 183 (2006)

    Article  CAS  Google Scholar 

  14. b)D. R. Richardson, The Lancet, 360, 501 (2002)

    Article  Google Scholar 

  15. c)G. J. Kontoghiorghes, A. Efstathiou, S. Ioannou-Loucaides, and A. Kolnagou, Hemoglobin, 32, 217 (2008)

    Article  CAS  Google Scholar 

  16. d)E. Yasumoto, K. Nakano, T. Nakayachi, S. R. M. Morshed, K. Hashimoto, H. Kikuchi, H. Nishikawa, M. Kawase, and H. Sakagami, Anticancer Res., 24, 755 (2004).

    CAS  Google Scholar 

  17. N. Chenoufi, B. Drénou, O. Loréal, C. Pigeon, P. Brissot, and G. Lescoat, Biochem. Pharmacol., 56, 431 (1998).

    Article  CAS  Google Scholar 

  18. a)H. Yadegari, A. Jabbari, H. Heli, A. Moosavi-Movahedi, and S. Majdi, J. Braz. Chem. Soc., 19, 1017 (2008)

    Article  CAS  Google Scholar 

  19. b)N. A. Georgiou, T. van der Bruggen, M. Oudshoorn, H. S. Nottet, J. J. Marx, and B. S. van Asbeck, J. Infect. Dis., 181, 484 (2000).

    Article  CAS  Google Scholar 

  20. C. Sappey, J. R. Boelaert, S. Legrand-Poels, C. Forceille, A. Favier, and J. Piette, AIDS Res. Hum. Retroviruses., 11, 1049 (1995).

    Article  CAS  Google Scholar 

  21. K. Ganeshaguru, A. V. Hoffbrand, R. W. Grady, and A. Cerami, Biochem. Pharmacol., 29, 1275 (1980).

    Article  CAS  Google Scholar 

  22. J. Tomasi, B. Mennucci, and R. Cammi, Chem. Rev., 105, 2999 (2005).

    Article  CAS  Google Scholar 

  23. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalman, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Jr. Montgomery, J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, and D. J. Fox, Gaussian 09. Revision A.02, Gaussian Inc., Wallingford, CT (2009).

    Google Scholar 

  24. R. Krishnan, J. S. Binkley, R. Seeger, and A. Pople, J. Chem. Phys., 72, 650 (1980).

    Article  CAS  Google Scholar 

  25. Y. Zhao and D. G. Truhla, J. Phys. Chem., 110, 5121 (2006).

    Article  CAS  Google Scholar 

  26. A. E. Reed, L. A. Curtiss, and F. Weinhold, Chem. Rev., 88, 899 (1988).

    Article  CAS  Google Scholar 

  27. E. D. Glendening, A. E. Reed, J. E. Carpenter, and F. Weinhold, NBO, version 3.1.

  28. M. H. Jamroz, Vibrational Energy Distribution Analysis: VEDA 4 Program, Warsaw (2004).

    Google Scholar 

  29. K. Wolinski, J. F. Hinton, and P. Pulay, J. Am. Chem. Soc., 112, 8251 (1990).

    Article  CAS  Google Scholar 

  30. E. Runge and E. K. U. Gross, Phys. Rev. Lett., 52, 997 (1984).

    Article  CAS  Google Scholar 

  31. W. Nelson, I. Kappishins, E. Rettig, and C. Rvig, Can. J. Chem., 66, 123 (1988).

    Article  CAS  Google Scholar 

  32. W. Yang and W. J. Mortier, J. Am. Chem. Soc., 108, 5708 (1986).

    Article  CAS  Google Scholar 

  33. L. Onsager, J. Am. Chem. Soc., 58, 1486 (1936).

    Article  CAS  Google Scholar 

  34. a)P. C. Ray and J. Leszczynski, Chem. Phys. Lett., 339, 162 (2004)

    Article  Google Scholar 

  35. b)K. Clays and A. Persoons, Phys. Rev. Lett., 66, 2980 (1991)

    Article  CAS  Google Scholar 

  36. c)H. Lee, S.-Y. An, and M. Cho, J. Phys. Chem. B, 103, 4992 (1999).

    Article  CAS  Google Scholar 

  37. a)N. P. G. Roeges, A Guide to Complete Interpretation of IR Spectra of Organic Structures, Wiley, New York (1994)

    Google Scholar 

  38. b)N. B. Colthup, L. H. Daly, and S. E. Wiberly, Introduction to Infrared and Raman Spectroscopy, Academic Press, New York (1975).

    Google Scholar 

  39. Y. Yang, W. J. Zhang, and X. M. Gao, Int. J. Quantum Chem., 106, 1199 (2006).

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Medical Nanotechnology, Faculty of Advanced Medical Sciences, Tabriz University of Medical Sciences, Tabriz, Iran

    A. Valizadeh

  2. Student Research Committee, Tabriz University of Medical Sciences, Tabriz, Iran

    A. Valizadeh

  3. Department of Medical Nanotechnology, School of Advanced Technologies in Medicine, Tehran University of Medical Sciences, Tehran, Iran

    A. Valizadeh

  4. Department of Chemistry, East Tehran Branch, Islamic Azad University, Tehran, Iran

    R. Ghiasi

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  1. A. Valizadeh
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  2. R. Ghiasi
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Correspondence to R. Ghiasi.

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Original Russian Text © 2017 A. Valizadeh, R. Ghiasi.

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Valizadeh, A., Ghiasi, R. Theoretical approach to the molecular structure, chemical reactivity, molecular orbital analysis, spectroscopic properties (IR, UV, NMR), and NBO analysis of deferiprone. J Struct Chem 58, 1307–1317 (2017). https://doi.org/10.1134/S002247661707006X

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  • DOI: https://doi.org/10.1134/S002247661707006X

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