Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Multiconfiguration Molecular Mechanics Studies for the Potential Energy Surfaces of the Excited State Double Proton Transfer in the 1:1 7-Azaindole:H2O Complex

  • Han, Jeong-A (Department of Chemistry, Kyung Hee University) ;
  • Kim, Yong-Ho (Department of Chemistry, Kyung Hee University)
  • Published : 2010.02.20
Download PDF
⟨ Previous Next ⟩

Abstract

The multiconfiguration molecular mechanics (MCMM) algorithm was used to generate potential and vibrationally adiabatic energy surfaces for excited-state tautomerization in the 1:1 7-azaindole:$H_2O$ complex. Electronic structures and energies for reactant, product, transition state were computed at the CIS/6-31G(d,p) level of theory. The potential and vibrationally adiabatic energies along the reaction coordinate were generated step by step by using 16 high-level Shepard points, which were computed at the CIS/6-31G(d,p) level. This study shows that the MCMM method was applied successfully to make quite reasonable potential and adiabatic energy curves for the excited-state double proton transfer reaction. No stable intermediates are present in the potential energy curve along the reaction coordinate of the excited-state double proton transfer in the 1:1 7-azaindole:$H_2O$ complex, indicating that these two protons are transferred concertedly. The change in the bond distances along the reaction coordinate shows that two protons move very asynchronously to make an $H_3O^+$-like moiety at the transition state.

Keywords

References

  1. Taylor, C. A.; El-Bayoumi, M. A.; Kasha, M. Proc. Natl. Acad. Aci. U.S.A. 1969, 63, 253. https://doi.org/10.1073/pnas.63.2.253
  2. Chaban, G. M.; Gordon, M. S. J. Phys. Chem. A 1999, 103, 185. https://doi.org/10.1021/jp9837838
  3. Gordon, M. S. J. Phys. Chem. 1996, 100, 3974. https://doi.org/10.1021/jp952851c
  4. Huang, Y.; Arnold, S.; Sulkes, M. J. Phys. Chem. 1996, 100, 4734. https://doi.org/10.1021/jp951183s
  5. Chapman, C. F.; Maroncelli, M. J. Phys. Chem. 1992, 96, 8430. https://doi.org/10.1021/j100200a042
  6. Chen, Y.; Gai, F.; Petrich, J. W. J. Am. Chem. Soc. 1993, 115, 10158. https://doi.org/10.1021/ja00075a035
  7. Chou, P.-T.; Martinez, M. L.; Cooper, W. C.; McMorrow, D.; Collins, S. T.; Kasha, M. J. Phys. Chem. 1992, 96, 5203. https://doi.org/10.1021/j100192a002
  8. Kwon, O.-H.; Jang, D.-J. J. Phys. Chem. B 2005, 109, 20479. https://doi.org/10.1021/jp053187v
  9. Kwon, O.-H.; Lee, Y.-S.; Park, H. J.; Kim, Y.; Jang, D.-J. Angew. Chem. 2004, 43, 5792. https://doi.org/10.1002/anie.200461102
  10. Mente, S.; Maroncelli, M. J. Phy. Chem. A 1998, 102, 3860. https://doi.org/10.1021/jp980771d
  11. Moog, R. S.; Maroncelli, M. J. Phy. Chem. 1991, 95, 10359. https://doi.org/10.1021/j100178a023
  12. Waluk, J. Acc. Chem. Res. 2003, 36, 832. https://doi.org/10.1021/ar0200549
  13. Chou, P. T.; Yu, W. S.; Wei, C. Y.; Cheng, Y. M.; Yang, C. Y. J. Am. Chem. Soc. 2001, 123, 3599. https://doi.org/10.1021/ja002975p
  14. Hsieh, W.-T.; Hsieh, C.-C.; Lai, C.-H.; Cheng, Y.-M.; Ho, M.-L.; Wang, K. K.; Lee, G.-H.; Chou, P.-T. Chem. Phys. Chem. 2008, 9, 293. https://doi.org/10.1002/cphc.200700578
  15. Kina, D.; Nakayama, A.; Noro, T.; Taketsugu, T.; Gordon, M. S. J. Phys. Chem. A 2008, 112, 9675. https://doi.org/10.1021/jp804368p
  16. Hung, F.-T.; Hu, W.-P.; Li, T.-H.; Cheng, C.-C.; Chou, P.-T. J. Phys. Chem. A 2003, 107, 3244. https://doi.org/10.1021/jp021620k
  17. Kyrychenko, A.; Waluk, J. J. Phys. Chem. A 2006, 110, 11958. https://doi.org/10.1021/jp063426u
  18. Nam, K.; Kim, Y. J. Chem. Phys. 2009, 130, 144310. https://doi.org/10.1063/1.3113662
  19. Podolyan, Y.; Gorb, L.; Leszczynski, J. J. Phys. Chem. A 2002, 106, 12103. https://doi.org/10.1021/jp021666d
  20. Kim, Y.; Lim, S.; Kim, Y. J. Phys. Chem. A 1999, 103, 6632. https://doi.org/10.1021/jp990398p
  21. Lim, J.-H.; Lee, E. K.; Kim, Y. J. Phys. Chem. A 1997, 101, 2233. https://doi.org/10.1021/jp9626226
  22. Kim, Y.; Corchado, J. C.; Villa, J.; Xing, J.; Truhlar, D. G. J. Chem. Phys. 2000, 112, 2718. https://doi.org/10.1063/1.480846
  23. Kim, Y. J. Phys. Chem. A 2005, 110, 600. https://doi.org/10.1021/jp0530193
  24. Ischtwan, J.; Collins, M. J. Chem. Phys. 1994, 100, 8080. https://doi.org/10.1063/1.466801
  25. Nguyen, K. A.; Rossi, I.; Truhlar, D. G. J. Chem. Phys. 1995, 5522.
  26. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Gaussian, Inc.: Wallingford, CT, 2004
  27. Garrett, B. C.; Truhlar, D. G.; Grev, R. S.; Magnuson, A. W. J. Phys. Chem. 1980, 84, 1730. https://doi.org/10.1021/j100450a013
  28. Truhlar, D. G.; Isaacson, A. D.; Garrett, B. C. In Theory of Chemical Reaction Dynamics; Baer, M., Ed.; CRC Press: Boca Raton, FL, 1985; Vol. 4, p 65.
  29. Liu, Y.-P.; Lynch, G. C.; Truong, T. N.; Lu, D.-H.; Truhlar, D. G.; Garrett, B. C. J. Am. Chem. Soc. 1993, 115, 2408. https://doi.org/10.1021/ja00059a041
  30. Skodje, R. T.; Truhlar, D. G.; Garrett, B. C. J. Phys. Chem. 1981, 85, 3019. https://doi.org/10.1021/j150621a001
  31. Garrett, B. C.; Joseph, T.; Truong, T. N.; Truhlar, D. G. Chem. Phys. 1989, 136, 271. https://doi.org/10.1016/0301-0104(89)80052-7
  32. Fernandez-Ramos, A.; Truhlar, D. G. J. Chem. Phys. 2001, 114, 1491. https://doi.org/10.1063/1.1329893
  33. Corchado, J. C.; Chuang, Y.-Y.; Fast, P. L.; Villa, J.; W.-P. Hu; Liu, Y.-P.; Lynch, G. C.; Nguyen, A.; Jackels, C. F.; V. S. Melissas; Lynch, B. J.; Rossi, I.; Coitino, E. L.; Fernandez-Ramos, A.; Pu, J.; Steckler, R.; Garrett, B. C.; Isaacson, A. D.; Truhlar, D. G. POLYRATE 8.7.2, University of Minnesota, Minneapolis, 2002.
  34. Albu, T. V.; Corchado, J. C.; Kim, Y.; Villa, J.; Xing, J.; Truhlar, D. G. MC-TINKERATE 8.8, University of Minnesota, Minneapolis, 2002.
  35. Corchado, J. C.; Chuang, Y.-Y.; Fast, P. L.; Hu, W.-P.; Liu, Y.-P.; Lynch, G. C.; Nguyen, K. A.; Jackels, C. F.; Ramos, A. F.; Ellingson, B. A.; Lynch, B. J.; Zheng, J.; Melissas, V. S.; Villa, J.; Rossi, I.; Coitino, E. L.; Pu, J.; Albu, T. V.; Steckler, R.; Garrett, B. C.; Isaacson, A. D.; Truhlar, D. G. Polyrate-version 9.7, University of Minnesota, Minneapolis, U.S.A., 2007
  36. Albu, T. V.; Corchado, J. C.; Kim, Y.; Villa, J.; Xing, J.; Truhlar, D. G. MC-TINKER 1.0, University of Minnesota, Minneapolis, 2002
  37. Sakota, K.; Sekiya, H. J. Phys. Chem. A 2009, 113, 2663. https://doi.org/10.1021/jp900128d