Skip to main content
SpringerLink
Log in
Book cover

Fundamental World of Quantum Chemistry pp 581–599Cite as

Hydrogen Bonding and the Energetics of Homolytic Dissociation in Solution

A Sequential Monte Carlo/Quantum Mechanics Approach

  • Chapter

  • 469 Accesses

Abstract

We discuss recent applications of microsolvation modeling and statistical mechanics Monte Carlo simulations to the energetics of homolytic bond dissociation in solution. This process, which generates free radical species in liquid phase is ubiquitous in many reactions of fundamental interest in chemistry and biochemistry including green plant photosynthesis and biocatalysis. Basic concepts of the microsolvation and Monte Carlo approaches to the energetics of homolytic bond dissociation in solution are reviewed and fundamentals of the sequential Monte Carlo/Quantum mechanics methodology are presented. By carrying out sequential Monte Carlo/Quantum mechanics calculations we stress the limitations of gas phase calculations based on local models such as microsolvation or hydrogen-bond-only and the importance of the statistical analysis of the solvation process for the understanding of the homolytic bond cleavage in solution. We give special emphasis to the relationship between solutesolvent hydrogen bonding, long-ranged interactions in polar solvents, and the energetics of homolytic bond dissociation.

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

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   299.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   379.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD   379.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. B. Halliwel and J. H. C. Gutteridge, Free Radicals in Biologygy and Medicine (Oxford University Press, Oxford, 1989).

    Google Scholar 

  2. E. C. Weaver, Annu. Rev. Plant. Physiol., 19, 426 (1968).

    Article  Google Scholar 

  3. S. Itoh, M. Taki, S. Fukuzumi, Coord. Chem. Rev., 198, 3 (2000).

    Article  CAS  Google Scholar 

  4. V. E. Kagan and Y. Y. Tyurina, Ann. N. Y. Acad. Sci., 854 (1998).

    Google Scholar 

  5. W. H. Kopenol, Free Radical Biol. Med., 10, 85 (1991).

    Article  Google Scholar 

  6. E. R. Stadman, Annu. Rev. Biochem., 62, 797 (1993).

    Article  Google Scholar 

  7. B. Aydogan, D. T. Marshall, S. G. Swarts, J. E. Turner, A. J. Boone, N. G. Richards, and W. E. Bolch, Radiat. Res. 157, 38 (2002).

    Article  CAS  Google Scholar 

  8. J. Foosey, D. Lefort, and J. Sorba, Free Radicals in Organic Chemistry (Wiley, New York, 1995).

    Google Scholar 

  9. R. M. Borges dos Santos and J. A. Martinho Simôes, J. Phys. Chem. Ref. Data, 27, 707 (1998).

    Article  CAS  Google Scholar 

  10. J. M. Kanabus-Kaminska, B. C. Gilbert, and D. J. Griller, J. Am. Chem. Soc., 111, 3311 (1989)

    Article  CAS  Google Scholar 

  11. F. G. Bordwell and L. J. Wei-Zhang, J. Am. Chem. Soc., 118, 10819 (1996).

    Article  CAS  Google Scholar 

  12. D. D. M. Wayner, E. Lusztyk, D. Pagé, K. U. Ingold, P. Mulder, L. J. J. Laarhoven, and H. S. Aldrich, J. Am. Chem. Soc., 117, 8737 (1995).

    Article  CAS  Google Scholar 

  13. R. C. Guedes, K. Coutinho, B. J. Costa Cabral, and S. Canuto, J. Phys. Chem. B, 107, 4304 (2003).

    Article  Google Scholar 

  14. R. C. Guedes, K. Coutinho, B. J. Costa Cabral, S. Canuto, C. F. Correia, R. M. Borges dos Santos, and J. A. Martinho Simões, J. Phys. Chem. A, 107, 9197 (2003).

    Article  CAS  Google Scholar 

  15. J. S. Wright, D. J. Carpenter, D. J. McKay, and K. U. Ingold, J. Am. Chem. Soc., 119, 4245 (1997).

    Article  CAS  Google Scholar 

  16. J. S. Wright, E. R. Johnson, and G. A. DiLabio, J. Am. Chem. Soc., 123, 1173 (2001).

    Article  CAS  Google Scholar 

  17. T. Brinck, M. Haeberlein, and M. Jonsson, J. Am. Chem. Soc., 119, 4239 (1997).

    Article  CAS  Google Scholar 

  18. Y.-D. Wu and D. K. W. Lai, J. Org. Chem., 61, 7904 (1996).

    Article  CAS  Google Scholar 

  19. A. K. Chandra and T. Uchimaru, Int. J. Mol. Sci., 3, 407 (2002).

    Article  CAS  Google Scholar 

  20. P. C. do Couto, R. C. Guedes, B. J. Costa Cabral, and J. A. Martinho Simões, Int. J. Quant. Chem., 86, 297 (2002).

    Article  Google Scholar 

  21. A. K. Chandra, P. C. Nam, and M. T. Nguyen, J. Phys. Chem. A, 107, 9182 (2003).

    Article  CAS  Google Scholar 

  22. E. R. Johnson, O. J. Clarkin, and G. A. DiLabio, J. Phys. Chem. A, 107, 9953 (2003).

    Article  CAS  Google Scholar 

  23. X. Q. Yao, X. J. Hou, H. J. Jiao, H. W. Xiang, and Y. W. Li, J. Phys. Chem. A, 107, 9991 (2003).

    Article  CAS  Google Scholar 

  24. N. Matsunaga, D. W. Rogers, and A. A. Zavitsas, J. Org. Chem., 68, 3158 (2003).

    Article  CAS  Google Scholar 

  25. R. S. Drago, A. P. Dadmun, and G. C. Vogel, Inorg. Chem., 32, 2473 (1993).

    Article  CAS  Google Scholar 

  26. G. C. Vogel and R. S. Drago, J. Chem. Educ., 73, 701 (1996).

    Article  CAS  Google Scholar 

  27. R. S. Drago, Applications of Electrostatic-Covalent Models in Chemistry (Surfside: Gainesville, FL, 1994).

    Google Scholar 

  28. R. C. Guedes, B. J. Costa Cabral, J. A. Martinho Simões, and H. P. Diogo, J. Phys. Chem. A, 104, 6062 (2000).

    Article  CAS  Google Scholar 

  29. J. A. Fernandez, J. Yao, and E. R. Bernstein, J. Chem. Phys., 107, 3363 (1997).

    Article  CAS  Google Scholar 

  30. J. A. Fernandez, J. Yao, and E. R. Bernstein, J. Chem. Phys., 110, 5159 (1999).

    Article  CAS  Google Scholar 

  31. J. Yao, J. A. Fernandez, and E. R. Bernstein, J. Chem. Phys., 110, 5174 (1999).

    Article  CAS  Google Scholar 

  32. J. A. Fernandez, J. Yao, and E. R. Bernstein, J. Chem. Phys., 110, 5183 (1999).

    Article  CAS  Google Scholar 

  33. D. M. Chipman, J. Phys. Chem. A, 103, 11181 (1999).

    CAS  Google Scholar 

  34. D. Sicinska, P. Paneth, and D. G. Truhlar, J. Phys. Chem. B, 106, 2708 (2002).

    Article  CAS  Google Scholar 

  35. O. Tapia and O. Goscinsky, Mol. Phys., 29, 1653 (1975).

    Article  CAS  Google Scholar 

  36. J. L. Rivail and D. Rinaldi, Chem. Phys., 18, 233(1976).

    Article  CAS  Google Scholar 

  37. S. Miertus, E. Scrocco, and J. Tomasi, Chem. Phys., 55, 117 (1981).

    Article  CAS  Google Scholar 

  38. C. J. Cramer and D. G. Truhlar, J. Am. Chem. Soc., 113, 8305 (1991); ibid, Chem. Rev., 99, 2161 (1999).

    Article  CAS  Google Scholar 

  39. E. G. Bakalbassis, A. T. Lithoxoidon, and A. P. Vafladis, J. Phys. Chem. A, 107, 8594 (2003).

    Article  CAS  Google Scholar 

  40. D. Frenkel and B. Smit, Understanding Molecular Simulation (Academic Press: San Diego, CA, 1996).

    Google Scholar 

  41. M. T. Nguyen, E. S. Kryachko, and L. G. Vanquickenborne in The Chemistry of Phenols, Patai’s Series, Ed. by Z. Rappoport (Wiley: London, 2003, pg. 1–198).

    Chapter  Google Scholar 

  42. B. J. Costa Cabral, R. G. Bakker Fonseca, and J. A. Martinho Simões, Chem. Phys. Lett., 258, 436 (1996).

    Article  CAS  Google Scholar 

  43. O. Tishchenko, E. S. Kryachko, and M. T. Nguyen, Spectrochim. Acta A, 58, 1951 (2002).

    Article  Google Scholar 

  44. O. Tishchenko, N. N. Pham-Tran, E. S. Kryachko, and M. T. Nguyen, J. Phys. Chem. A, 105, 8709 (2001).

    Article  CAS  Google Scholar 

  45. O. Tishchenko, E. S. Kryachko, and M. T. Nguyen, J. Mol. Struct., 615, 247 (2002).

    Article  CAS  Google Scholar 

  46. B. Silvi, E. S. Kryachko, O. Tishchenko, F. Fuster, and M. T. Nguyen, Mol. Phys., 100, 1659 (2002).

    Article  CAS  Google Scholar 

  47. Y. Qin and R. A. Wheeler, J. Chem. Phys., 102, 1689 (1995).

    Article  CAS  Google Scholar 

  48. V. B. Luzhkov and A. S. Zyubin, J. Mol. Struct. (Theochem), 47, 33 (1988).

    Article  CAS  Google Scholar 

  49. M. Foti, K. U. Ingold, and J. Lusztyk, J. Am. Chem. Soc., 116, 9440 (1994).

    Article  CAS  Google Scholar 

  50. R. F. Liu, K. Morokuma, A. M. Mebel, and M. C. Liu, J. Phys. Chem., 100, 9314 (1996).

    Article  CAS  Google Scholar 

  51. S. Canuto and K. Coutinho, Adv. Quantum Chem., 28, 90 (1997).

    Google Scholar 

  52. S. Canuto, K. Coutinho and D. Trzesniak, Adv. Quantum Chem., 41, 161 (2002).

    Article  CAS  Google Scholar 

  53. K. Coutinho and S. Canuto, J. Mol. Structure (Theochem), 632, 235 (2003).

    Article  CAS  Google Scholar 

  54. D. Feller and M. W. Feyereisen, J. Comput. Chem., 14, 1027 (1993).

    Article  CAS  Google Scholar 

  55. H. Watanabe and S. Iwata, J. Chem. Phys., 105, 420 (1996).

    Article  CAS  Google Scholar 

  56. M. Sodupe, A. Oliva, and J. Bertran, J. Phys. Chem. A, 101, 9142 (1997).

    Article  CAS  Google Scholar 

  57. Y. Dimitrova, J. Mol. Struct. (Theochem), 455, 9 (1998).

    Article  CAS  Google Scholar 

  58. D. M. Benoit and D. C. Clary, J. Phys. Chem. A, 104, 5590 (2000).

    Article  CAS  Google Scholar 

  59. H. H. Y. Tsui and T. van Mourik, Chem. Phys. Lett., 350, 565 (2001).

    Article  CAS  Google Scholar 

  60. A. L. Sobolewski and W. Domcke, J. Phys. Chem. A, 105, 9275 (2001).

    Article  CAS  Google Scholar 

  61. E. S. Kryachko and H. Nakatsuji, J. Phys. Chem. A, 106, 731 (2002).

    Article  CAS  Google Scholar 

  62. N. Yamamoto, N. Shida, and E. Miyoshi, Chem. Phys. Lett., 371, 724 (2003).

    Article  CAS  Google Scholar 

  63. P. C. do Couto, R. C. Guedes, B. J. Costa Cabral, and J. A. Martinho Simões, J. Chem. Phys., 119, 7344 (2003).

    Article  Google Scholar 

  64. 64 S. G. Estácio, P. C. do Couto, R. C. Guedes, B. J. Costa Cabral, and J. A. Martinho Simões, Theor. Chem. Accounts (in press).

    Google Scholar 

  65. V. N. Levchuk, I. I. Sheyket, and B. Ya. Simkin, Chem. Phys. Lett., 185, 339 (1991).

    Article  CAS  Google Scholar 

  66. T. Lazaridis, J. Phys. Chem. B, 104, 4964 (2000).

    Article  CAS  Google Scholar 

  67. P. A. Steiner and W. Gordy, J. Mol. Spectrosc., 21, 291 (1966).

    Article  CAS  Google Scholar 

  68. S. Scheiner, Hydrogen Bonding: A Theoretical Perspective (Oxford University Press, New York, 1997).

    Google Scholar 

  69. S. Scheiner, T. Kar and Y. Gu, J. Biol. Chem. 276, 9832 (2001)

    Article  CAS  Google Scholar 

  70. S. Scheiner, T. Kar, and J. Pattanayak, J. Am. Chem. Soc., 124, 13257 (2002).

    Article  CAS  Google Scholar 

  71. A. A. Stolov, D. I. Kamalova, M. D. Barisover, and B. N. Solomonov, Spectrochim. Acta A, 50, 145 (1994).

    Article  Google Scholar 

  72. E. S. Kryachko and M. T. Nguyen, J. Phys. Chem. A, 105, 153 (2001).

    Article  CAS  Google Scholar 

  73. R. M. B. dos Santos, V. S. F. Muralha, C. F. Correia, and J. A. Martinho Simões, J. Am. Chem. Soc., 123, 12670 (2001).

    Article  Google Scholar 

  74. J. B. Foresman, T. A. Keith, K. B. Wiberg, J. Snoonian, and M. J. Frisch, J. Phys. Chem., 100, 16098 (1996).

    Article  CAS  Google Scholar 

  75. J. Tomasi, R. Cammi, B. Menucci, C. Capella, and S. Corni, Phys.Chem.Chem.Phys., 4, 5697 (2002).

    Article  CAS  Google Scholar 

  76. T. Malaspina, K. Coutinho and S. Canuto, J. Chem. Phys. 117, 1692 (2002).

    Article  CAS  Google Scholar 

  77. E. E. Flleti, K. Coutinho, T. Malaspina and S. Canuto, Phys. Rev. E 67, 61504 (2003).

    Article  Google Scholar 

  78. E. E. Fileti, K. Coutinho and S. Canuto, Adv. Quantum Chem., in press.

    Google Scholar 

  79. H. J. C. Berendsen, J. P. M. Postma, W. F. van Gusteren, and J. Hermans. In Intermolecular Forces, Ed. B. Pullman. (Reidel: Dordrecht, The Netherlands, 1981, pg. 331).

    Google Scholar 

  80. K. Coutinho and S. Canuto. DICE: A general Monte Carlo program for liquid simulation; University of São Paulo, São Paulo, Brazil (2000).

    Google Scholar 

  81. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratman, J. C. Burant, S. Dapprich, J. M. Millan, A. D. Daniels, K. N. Nudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Peterson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, W. Wong, J. L. Andres, M. Head-Gordon, E. S. Repogle, J. A. Pople, GAUSSIAN-98, Gaussian Inc., Pittsburgh, PA (1998).

    Google Scholar 

  82. M. Mezei and D. L. Beveridge, J. Chem. Phys., 74, 622 (1981).

    Article  CAS  Google Scholar 

  83. F. H. Stillinger, Adv. Chem. Phys. 31, 1 (1975).

    Article  CAS  Google Scholar 

  84. S. F. Boys and F. Bernardi, Mol. Phys. 19, 553 (1970).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Instituto de Física, Universidade de São Paulo, CP 66318, 05315-970, São Paulo, Brazil

    Sylvio Canuto

  2. Universidade de Mogi das Cruzes, CP 411, 0871-970, Mogi das Cruzes, SP, Brazil

    Kaline Coutinho

  3. Departamento de Química e Bioquímica and Grupo de Física Matemática, Universidade de Lisboa, Av. Prof. Gama Pinto, 2, 1649-003, Lisboa, Portugal

    Benedito J. Costa Cabral

Authors
  1. Sylvio Canuto
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Kaline Coutinho
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Benedito J. Costa Cabral
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Uppsala University, Uppsala, Sweden

    Erkki J. Brändas

  2. Bogoliubov Institute for Theoretical Physics, Kiev, Ukraine

    Eugene S. Kryachko

  3. University of Leuven, Leuven, Belgium

    Eugene S. Kryachko

Rights and permissions

Reprints and permissions

Copyright information

© 2004 Springer Science+Business Media Dordrecht

About this chapter

Cite this chapter

Canuto, S., Coutinho, K., Cabral, B.J.C. (2004). Hydrogen Bonding and the Energetics of Homolytic Dissociation in Solution. In: Brändas, E.J., Kryachko, E.S. (eds) Fundamental World of Quantum Chemistry. Springer, Dordrecht. https://doi.org/10.1007/978-94-017-0448-9_25

Download citation

  • DOI: https://doi.org/10.1007/978-94-017-0448-9_25

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-90-481-6687-9

  • Online ISBN: 978-94-017-0448-9

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation