Table of Contents Author Guidelines Submit a Manuscript
Journal of Chemistry
Volume 2013, Article ID 265958, 8 pages
http://dx.doi.org/10.1155/2013/265958
Research Article

Thermodynamic Study of Hydrolysis Reactions in Aqueous Solution from Ab Initio Potential and Molecular Dynamics Simulations

Departamento de Ingeniería Química y Química Física, Universidad de Extremadura, 06071 Badajoz, Spain

Received 28 June 2012; Accepted 1 August 2012

Academic Editor: Jose Corchado

Copyright © 2013 S. Tolosa et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. C. J. Cramer and D. G. Truhlar, Structure and Reactivity in Aqueous Solution, American Chemical Society, Washington, DC, USA, 1994.
  2. A. Warshel, Computer Modeling of Chemical Reactions in Enzymes and Solutions, John Wiley & Sons, New York, NY, USA, 1991.
  3. M. Moreau and P. Turq, Chemical Reactivity in Liquids. Fundamental Aspects, Plenum Press, New York, NY, USA, 1988.
  4. D. G. Truhlar, A. D. Isaacson, and B. C. Garret, The Theory of Chemical Reaction Dynamics, vol. 4, CRC Press, Boca Raton, Fla, USA, 1985.
  5. Bala, P. Grocowski, P. Lesyg B, and J. A. McCammon, in Quantum Mechanical Simulation Methods for Studying Biological Systems, D. Bicout and M. Field, Eds., Springer, Berlin, Germany, 1995.
  6. J. Gao, “Methods and aplications of combined quantum mechanical and molecular mechanical potentials,” in Review in Computational Chemistry, K. B. Lipkowitz and B. D. Boyd, Eds., vol. 7, VCH, New York, NY, USA, 1996. View at Google Scholar
  7. C. J. Cramer and D. G. Truhlar, “Continuum solvation models,” in Solvent Effects and Chemical Reactivity, O. Tapia and J. Bertran, Eds., Kluwer, Dordrecht, The Netherlands, 1996. View at Google Scholar
  8. D. Truhlar, “Direct dynamics method for the calculation of reaction rates,” in The Reaction Path in Chemistry: Current Approaches and Perspectives, D. Heidrich, Ed., Kluwer, Dordrecht, The Netherlands, 1995. View at Google Scholar
  9. R. Car and M. Parrinello, “Unified approach for molecular dynamics and density-functional theory,” Physical Review Letters, vol. 55, no. 22, pp. 2471–2474, 1985. View at Publisher · View at Google Scholar · View at Scopus
  10. S. Miertus, E. Scrocco, and J. Tomasi, “Electrostatic interaction of a solute with a continuum. A direct utilizaion of Ab initio molecular potentials for the prevision of solvent effects,” Chemical Physics, vol. 55, no. 1, pp. 117–129, 1981. View at Google Scholar · View at Scopus
  11. J. Gao, “Absolute free energy of solvation from Monte Carlo simulations using combined quantum and molecular mechanical potentials,” The Journal of Physical Chemistry, vol. 96, no. 2, pp. 537–540, 1992. View at Google Scholar · View at Scopus
  12. B. J. Alder and T. E. Wainwright, “Studies in molecular dynamics. I. General method,” Journal of Chemical Physics, vol. 31, no. 2, article 459, 8 pages, 1959. View at Google Scholar · View at Scopus
  13. S. Tolosa, J. A. Sansón, and A. Hidalgo, “The N-H O=C proton transfer in aqueous solution: a suitable procedure for extracting atomic charges,” Chemical Physics Letters, vol. 357, no. 3-4, pp. 279–286, 2002. View at Publisher · View at Google Scholar · View at Scopus
  14. S. Tolosa, J. A. Sansón, and A. Hidalgo, Recent Research Developments in Chemical Physics, Transworld Research Network, Trivandrum, India, 2002.
  15. S. Tolosa, J. A. Sansón, and A. Hidalgo, “Thermodynamic and dielectric properties of aqueous solutions using ESIE charges to describe small solutes,” Chemical Physics, vol. 293, no. 2, pp. 193–202, 2003. View at Publisher · View at Google Scholar · View at Scopus
  16. S. Tolosa, J. A. Sansón, and A. Hidalgo, “Theoretical-experimental study of the solvation enthalpy of acetone in dilute aqueous solution,” Chemical Physics, vol. 315, no. 1-2, pp. 76–80, 2005. View at Publisher · View at Google Scholar · View at Scopus
  17. S. Tolosa, J. A. Sansón, and A. Hidalgo, “Molecular dynamics simulation of acetamide solvation using interaction energy components: application to structural and energy properties,” Chemical Physics, vol. 327, no. 1, pp. 187–192, 2006. View at Publisher · View at Google Scholar · View at Scopus
  18. R. A. Marcus, “On the theory of oxidation-reduction reactions involving electron transfer. I,” Journal of Chemical Physics, vol. 24, no. 5, pp. 966–978, 1956. View at Google Scholar · View at Scopus
  19. R. Marcus, “Chemical and electrochemical electron-transfer theory,” Annual Review of Physical Chemistry, vol. 15, pp. 155–196, 1964. View at Publisher · View at Google Scholar
  20. R. A. Marcus, “Theoretical relations among rate constants, barriers, and Brønsted slopes of chemical reactions,” The Journal of Physical Chemistry, vol. 72, no. 3, pp. 891–899, 1968. View at Google Scholar · View at Scopus
  21. R. A. Marcus and N. Sutin, “The relation between the barriers for thermal and optical electron transfer reactions in solution,” Comments on Inorganic Chemistry, vol. 5, no. 3, pp. 119–133, 1986. View at Publisher · View at Google Scholar
  22. E. A. Carter and J. T. Hynes, “Solute-dependent solvent force constants for ion pairs and neutral pairs in a polar solvent,” The Journal of Physical Chemistry, vol. 93, no. 6, pp. 2184–2187, 1989. View at Google Scholar · View at Scopus
  23. H. Slebocka-Tilk, F. Sauriol, M. Monette, and R. S. Brown, “Aspects of the hydrolysis of formamide: revisitation of the water reaction and determination of the solvent deuterium kinetic isotope effect in base,” Canadian Journal of Chemistry, vol. 80, no. 10, pp. 1343–1350, 2002. View at Publisher · View at Google Scholar · View at Scopus
  24. M. H. Almatarneh, C. G. Flinn, and R. A. Poirier, “Ab initio study of the decomposition of formamidine,” Canadian Journal of Chemistry, vol. 83, no. 12, pp. 2082–2090, 2005. View at Publisher · View at Google Scholar · View at Scopus
  25. M. Nagaoka, Y. Okuno, and T. Yamabe, “The chemical reaction molecular dynamics method and the dynamic transition state: proton transfer reaction in the formamidine and water solvent system,” Journal of the American Chemical Society, vol. 113, no. 3, pp. 769–778, 1991. View at Google Scholar · View at Scopus
  26. J. P. Guthrie, “Hydration of carboxylic acids and esters. Evaluation of the free energy change for addition of water to acetic and formic acids and their methyl esters,” Journal of the American Chemical Society, vol. 95, no. 21, pp. 6999–7003, 1973. View at Google Scholar · View at Scopus
  27. J. P. Guthrie, “Hydration of thioesters. Evaluation of the free-energy changes for the addition of water to some thioesters, rate-equilibrium correlations over very wide ranges in equilibrium constants, and a new mechanistic criterion,” Journal of the American Chemical Society, vol. 100, no. 18, pp. 5892–5904, 1978. View at Google Scholar · View at Scopus
  28. G. Raspoet, M. T. Nguyen, M. McGarraghy, and A. F. Hegarty, “Experimental and theoretical evidence for a concerted catalysis by water clusters in the hydrolysis of isocyanates,” Journal of Organic Chemistry, vol. 63, no. 20, pp. 6867–6877, 1998. View at Publisher · View at Google Scholar · View at Scopus
  29. R. Ditchfield, W. J. Hehre, and J. A. Pople, “Self-consistent molecular-orbital methods. IX. An extended gaussian-type basis for molecular-orbital studies of organic molecules,” Journal of Chemical Physics, vol. 54, no. 2, article 724, 5 pages, 1971. View at Google Scholar · View at Scopus
  30. W. J. Hehre, K. Ditchfield, and J. A. Pople, “Self-consistent molecular orbital methods. XII. Further extensions of gaussian-type basis sets for use in molecular orbital studies of organic molecules,” Journal of Chemical Physics, vol. 56, no. 5, pp. 2257–2261, 1972. View at Google Scholar · View at Scopus
  31. K. Kitaura and K. Morokuma, “A new energy decomposition scheme for molecular interactions within the Hartree-Fock approximation,” International Journal of Quantum Chemistry, vol. 10, no. 2, pp. 325–340, 1976. View at Publisher · View at Google Scholar
  32. H. Umeyama and K. Morokuma, “The origin of hydrogen bonding. An energy decomposition study,” Journal of the American Chemical Society, vol. 99, no. 5, pp. 1316–1332, 1977. View at Google Scholar · View at Scopus
  33. W. L. Jorgensen and J. Tirado-Rives, “The OPLS potential functions for proteins. Energy minimizations for crystals of cyclic peptides and crambin,” Journal of the American Chemical Society, vol. 110, no. 6, pp. 1657–1666, 1988. View at Google Scholar · View at Scopus
  34. D. A. Case, T. A. Darden, I. T. E. Cheatham et al., AMBER 8, University of California, San Francisco, Calif, USA, 2004.
  35. P. Ewald, “Die Berechnung optischer und elektrostatischer Gitterpotentiale,” Annalen der Physik, vol. 64, no. 3, pp. 253–287, 1921. View at Publisher · View at Google Scholar
  36. J.-P. Ryckaert, G. Ciccotti, and H. J. C. Berendsen, “Numerical integration of the cartesian equations of motion of a system with constraints: molecular dynamics of n-alkanes,” Journal of Computational Physics, vol. 23, no. 3, pp. 327–341, 1977. View at Google Scholar · View at Scopus
  37. M. J. Frisch, G. W. Trucks, H. B. Schlegel et al., Gaussian 98, Revision A. 11. 3, Gaussian, Pittsburgh, Pa, USA, 2002.
  38. M. Dupuis, D. Spangler, and J. Wendoloski, GAMESS Program QG01, National Resource for Computations in Chemistry Software Catalog, University of California, Berkeley, Calif, USA, 1980.
  39. G. I. Almerindo and J. R. Pliego Jr., “Ab initio investigation of the kinetics and mechanism of the neutral hydrolysis of formamide in aqueous solution,” Journal of the Brazilian Chemical Society, vol. 18, no. 4, pp. 696–702, 2007. View at Google Scholar · View at Scopus
  40. S. Antonczak, M. Ruiz-López, and J.-L. Rivail, “The hydrolysis mechanism of formamide revisited: comparison between ab initio, semiempirical and DFT results,” Journal of Molecular Modeling, vol. 3, no. 10, pp. 434–442, 1997. View at Google Scholar · View at Scopus
  41. G. Estiu and K. M. Merz, “The hydrolysis of amides and the proficiency of amidohydrolases. The burden borne by kw,” The Journal of Physical Chemistry B, vol. 111, no. 23, pp. 6507–6519, 2007. View at Publisher · View at Google Scholar · View at Scopus
  42. L. Gorb, A. Asensio, I. Tuñón, and M. F. Ruiz-López, “The mechanism of formamide hydrolysis in water from Ab initio calculations and simulations,” Chemistry—A European Journal, vol. 11, no. 22, pp. 6743–6753, 2005. View at Publisher · View at Google Scholar · View at Scopus
  43. H. Ulrich, The Chemistry and Technology of Isocyanates, Wiley, New York, NY, USA, 1996.
  44. N. L. Poon and D. P. N. Satchell, “A comparison of the mechanisms of hydrolysis of diphenylketene and dimethylketene in diethyl ether solution,” Journal of the Chemical Society, Perkin Transactions 2, no. 9, pp. 1381–1383, 1983. View at Google Scholar · View at Scopus
  45. P. M. Mader, “Hydrolysis kinetics for p-dimethylaminophenyl isocyanate in aqueous solutions,” Journal of Organic Chemistry, vol. 33, no. 6, pp. 2253–2260, 1968. View at Google Scholar · View at Scopus
  46. T. D. J. D'Silva, A. Lopes, R. L. Jones, S. Singhawangcha, and J. K. Chan, “Studies of methyl isocyanate chemistry in the Bhopal incident,” Journal of Organic Chemistry, vol. 51, no. 20, pp. 3781–3788, 1986. View at Google Scholar · View at Scopus
  47. I. H. Williams, D. Spangler, D. A. Femec, G. M. Maggiora, and R. L. Schowen, “Theoretical models for solvation and catalysis in carbonyl addition,” Journal of the American Chemical Society, vol. 105, no. 1, pp. 31–40, 1983. View at Google Scholar · View at Scopus
  48. J. Barker, M. Jones, and M. Kilner, “Amidine mass spectral fragmentation patterns,” Organic Mass Spectrometry, vol. 20, no. 10, pp. 619–623, 1985. View at Publisher · View at Google Scholar
  49. J. Andres, J. Krechl, M. Carda, and E. Silla, “An Ab initio study of the unimolecular decomposition mechanism of formamidine. 4-31G Characterization of potential energy hypersurface,” International Journal of Quantum Chemistry, vol. 50, no. 1, pp. 127–137, 1991. View at Google Scholar
  50. J. Andrés, A. Beltran, M. Carda, J. Krechl, J. Monterde, and E. Silla, “Amidine decomposition mechanism. A theoretical study,” Journal of Molecular Structure, vol. 254, pp. 465–472, 1992. View at Google Scholar · View at Scopus
  51. R. Kaushik, R. C. Rastogi, and N. K. Ray, “Density functional study of the reaction paths of formamidine,” Indian Journal of Chemistry, vol. 35, no. 8, pp. 629–632, 1996. View at Google Scholar · View at Scopus
  52. J. F. Marlier, T. G. Frey, J. A. Mallory, and W. W. Cleland, “Multiple isotope effect study of the acid-catalyzed hydrolysis of methyl formate,” Journal of Organic Chemistry, vol. 70, no. 5, pp. 1737–1744, 2005. View at Publisher · View at Google Scholar · View at Scopus
  53. T. D. Vu, A. Seidel-Morgenstern, S. Grüner, and A. Kienle, “Analysis of ester hydrolysis reactions in a chromatographic reactor using equilibrium theory and a rate model,” Industrial and Engineering Chemistry Research, vol. 44, no. 25, pp. 9565–9574, 2005. View at Publisher · View at Google Scholar · View at Scopus
  54. C.-G. Zhan, D. W. Landry, and R. L. Ornstein, “Reaction pathways and energy barriers for alkaline hydrolysis of carboxylic acid esters in water studied by a hybrid supermolecule-polarizable continuum approach,” Journal of the American Chemical Society, vol. 122, no. 11, pp. 2621–2627, 2000. View at Publisher · View at Google Scholar · View at Scopus
  55. J. R. Pliego Jr. and J. M. Riveros, “A theoretical analysis of the free-energy profile of the different pathways in the alkaline hydrolysis of methyl formate in aqueous solution,” Chemistry—A European Journal, vol. 8, no. 8, pp. 1945–1953, 2002. View at Publisher · View at Google Scholar · View at Scopus
  56. H. Gunaydin and K. N. Houk, “Molecular dynamics prediction of the mechanism of ester hydrolysis in water,” Journal of the American Chemical Society, vol. 130, no. 46, pp. 15232–15233, 2008. View at Publisher · View at Google Scholar · View at Scopus
  57. K. Ando and J. T. Hynes, “Molecular mechanism of HCl acid ionization in water: Ab initio potential energy surfaces and Monte Carlo simulations,” The Journal of Physical Chemistry B, vol. 101, no. 49, pp. 10464–10478, 1997. View at Google Scholar · View at Scopus
  58. K. Ando and J. T. Hynes, “Molecular mechanism of HF acid ionization in water: an electronic structure-Monte Carlo study,” The Journal of Physical Chemistry A, vol. 103, no. 49, pp. 10398–10408, 1999. View at Google Scholar · View at Scopus
  59. M. Tachiya, “Relation between the electron-transfer rate and the free energy change of reaction,” The Journal of Physical Chemistry, vol. 93, no. 20, pp. 7050–7052, 1989. View at Google Scholar · View at Scopus