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A theoretical study of solvent effects on the characteristics of the intramolecular hydrogen bond in Droxidopa

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Abstract

The molecular structures and intramolecular hydrogen bond of Droxidopa have been investigated with density functional theory. It is found that strong hydrogen bonds (O–H...N and O...H–O) exist in the title compound. These hydrogen bonds play essential roles in determining conformational preferences and energy, which would have important effects in biological activity mechanisms that will strongly influence its characteristics in solution. A computational study of a representative number of actual and model structures was carried out in five solvents with different polarities and different types of interactions with solute molecules: water, ethanol, carbon tetrachloride, dimethyl sulfoxide, and tetrahydrofuran, utilizing the polarizable continuum model (PCM) model. The calculations were performed at the B3LYP/6-311 ++G(d,p) level of theory. In addition, the topological properties of the electron density distributions for O–H...N(O) intramolecular hydrogen bond were analyzed in terms of the Bader’s theory of atoms in molecules. Furthermore, the analyses of different hydrogen bonds in this molecule by quantum theory of natural bond orbital (NBO) methods support the density functional theory (DFT) results.

The molecular structures of Droxidopa have been investigated with density functional theory. A computational study of a representative number of actual and model structures was carried out in five solvents with different polarities: water, ethanol, carbon tetrachloride, dimethyl sulfoxide, and tetrahydrofuran, utilizing the polarizable continuum model.

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References

  1. Raissi H, Yoosefian M and Khoshkhou S 2012 Comput. Theor. Chem. 983 1

    Article  CAS  Google Scholar 

  2. Raissi H, Yoosefian M, Zamani S and Farzad F 2012 J. Sulfur Chem. 33 75

    Article  CAS  Google Scholar 

  3. Raissi H, Yoosefian M, Mollania F, Farzad F and Nowroozi A R 2011 Comput. Theor. Chem. 966 299

    Article  CAS  Google Scholar 

  4. Raissi H, Yoosefian M and Mollania F 2012 Int. J. Quantum Chem. 112 2782

    Article  CAS  Google Scholar 

  5. Dunitz J D, In X-ray Analysis and the Structure of Organic Molecules (London: Cornell University Press) (1979)

  6. Nadim E S, Raissi H, Yoosefian M, Farzad F and Nowroozi A R 2010 J. Sulfur Chem. 31 275

    Article  CAS  Google Scholar 

  7. Raissi H, Khanmohammadi A, Yoosefian M and Mollania F 2013 Struct. Chem. 24 1121

    Article  CAS  Google Scholar 

  8. Raissi H, Yoosefian M, Mollania F and Khoshkhou S 2013 Struct. Chem. 24 123

    Article  CAS  Google Scholar 

  9. Yoosefian M, Raissi H, Davamdar E, Esmaeili A and Azaroon M 2012 Chin. J. Chem. 30 779

    Article  CAS  Google Scholar 

  10. Yoosefian M, Raissi H, Nadim E S, Farzad F, Fazli M, Karimzade E and Nowroozi A 2011 Int. J. Quantum Chem. 111 3505

    CAS  Google Scholar 

  11. Raissi H, Jalbout A, Nasseria M, Yoosefian M, Ghiassi H and Hameed A 2008 Int. J. Quantum Chem. 108 1444

    Article  CAS  Google Scholar 

  12. Raissi H, Yoosefian M, Hajizadeh A, Karimi M and Farzad F 2012 Bull. Chem. Soc. Jpn. 85 87

    Article  CAS  Google Scholar 

  13. Raissi H, Nadim E S, Yoosefian M, Farzad F, Ghiamati E, Nowroozi A R, Fazli M and Amoozadeh A 2010 J. Mol. Struct. Theochem. 960 1

    Article  CAS  Google Scholar 

  14. Meng-Xia X and Yuan L 2002 Spectrochim. Acta, Part A 58 2817

    Article  Google Scholar 

  15. Schlücker S, Singh R K, Asthana B, Popp J and Kiefer W 2001 J. Phys. Chem. A 105 9983

    Article  Google Scholar 

  16. Bonaccorsi R, Palla P and Tomasi J 1984 J. Am. Chem. Soc. 106 1945

    Article  CAS  Google Scholar 

  17. Del Valle F and Tomasi J 1987 Chem. Phys. 114 231

    Article  Google Scholar 

  18. Mammino L and Kabanda M M 2009 J. Phys. Chem. A 113 15064

    Article  CAS  Google Scholar 

  19. Alagona G, Ghio C, Igual J and Tomasi J 1990 J. Mol. Struct. Theochem 204 253

    Article  Google Scholar 

  20. Barone V, Cossi M and Tomasi J 1997 J. Chem. Phys. 107 3210

    Article  CAS  Google Scholar 

  21. Cossi M, Scalmani G, Rega N and Barone V 2002 J. Chem. Phys. 117 43

    Article  CAS  Google Scholar 

  22. Holmquist M, Hæffner F, Norin T and Hult K 1996 Protein Sci. 5 83

    Article  CAS  Google Scholar 

  23. Bonaccorsi R, Hodošček M and Tomasi J 1988 J. Mol. Struct. THEOCHEM. 164 105

    Article  Google Scholar 

  24. Nogrady T and Weaver D F 2005 In Medicinal Chemistry: A molecular and biochemical approach (New York: Oxford University Press)

  25. Goldstein D S 2006 Cardiovasc. Drug Rev. 24 189

    Article  CAS  Google Scholar 

  26. Mathias C J 2008 Clin. Auton. Res. 18 25

    Article  Google Scholar 

  27. Tomasi J and Persico M 1994 Chem. Rev. 94 2027

    Article  CAS  Google Scholar 

  28. Tomasi J, Mennucci B and Cammi R 2005 Chem. Rev. 105 2999

    Article  CAS  Google Scholar 

  29. Frisch M, Trucks G, Schlegel H, Scuseria G, Robb M, Cheeseman J, Montgomery Jr. J, Vreven T, Kudin K and Burant J, Gaussian 03, Rev B. 03. (Gaussian Inc, Pittsburgh, PA) (2003)

  30. Biegler-Konig F 1998 In AIM 2000 (Germany: University of Applied Science)

  31. Glendening E, Reed A, Carpenter J and Weinhold F, NBO, version 3.1. (Pittsburgh PA) (1988)

  32. Schuster P, Zundel G and Sandorfy C (Eds.) 1976 Hydrogen bond; recent developments in theory and experiments (Amsterdam: North-Holland Publishing Company)

  33. Espinosa E, Molins E and Lecomte C 1998 Chem. Phys. Lett. 285 170

    Article  CAS  Google Scholar 

  34. Abramov Y A 1997 Acta Crystallogr. Sect. A 53 264

    Article  Google Scholar 

  35. Bader R F 1990 In Atoms in Molecules: A Quantum Theory (Oxford: Oxford University Press)

    Google Scholar 

  36. Popelier P, Aicken F and O’Brien S 2000 Chemical Modelling: Applications and Theory 1 143

    Article  CAS  Google Scholar 

Download references

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Authors and Affiliations

  1. Department of Chemistry, Graduate University of Advanced Technology, Kerman, Iran

    MEHDI YOOSEFIAN, HASSAN KARIMI-MALEH & AFSANEH L SANATI

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  1. MEHDI YOOSEFIAN
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  2. HASSAN KARIMI-MALEH
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YOOSEFIAN, M., KARIMI-MALEH, H. & SANATI, A.L. A theoretical study of solvent effects on the characteristics of the intramolecular hydrogen bond in Droxidopa. J Chem Sci 127, 1007–1013 (2015). https://doi.org/10.1007/s12039-015-0858-2

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