Density functional theory (DFT) and natural bond orbital (NBO) investigation of intramolecular hydrogen bond interaction and excited-state intramolecular proton transfer (ESIPT) reaction in a five-membered hydrogen-bonding system 2-(1H-pyrazol-5-yl)pyridine: On the possibility of solvent (water)-assisted ESPT

Computational and Theoretical Chemistry

Volumn 972, Issue 1-3, 2011, Pages 1-13

  Paul, Bijan Kumar ^a   Guchhait, Nikhil ^a  

^a UNIVERSITY OF CALCUTTA   (India)

Author keywords

DFT; ESIPT; Hydrogen bonding; NBO; Water assisted ESPT

Indexed keywords

EID: 84555190719     PISSN: 2210271X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.comptc.2011.06.004     Document Type: Article

References (61)

1. Weller A.H. Prog. React. Kinet. 1961, 1:187-213.
2. Singh R.B., Mahanta S., Kar S., Guchhait N. Chem. Phys. 2007, 331:373-384.
3. Douhal A., Lahmani F., Zewail A. Chem. Phys. 1996, 207:477-498.
4. Paul B.K., Samanta A., Guchhait N. J. Mol. Struct. 2010, 977:78-89.
5. Paul B.K., Samanta A., Guchhait N. Photochem. Photobiol. Sci. 2010, 9:57-67.
6. Mandal A., Guha D., Mukherjee S. J. Mol. Spectrosc. 2001, 210:183-190.
7. Mishra H., Joshi H.C., Tripathi H.B., Maheshwary S., Sathyamurthy N., Panda M., Chandrasekhar J. J. Photochem. Photobiol. A: Chem. 2001, 139:23-36.
8. Paul B.K., Samanta A., Kar S., Guchhait N. J. Photochem. Photobiol. A: Chem. 2010, 214:203-214.
9. Sobolewski A.L., Domcke W. Chem. Phys. 1998, 232:257-265.
10. Pant D.D., Joshi H.C., Bisht P.B., Tripathi H.B. Chem. Phys. 1994, 185:137-144.
11. Yahagi T., Fujii A., Ebata T., Mikami N. J. Phys. Chem. A 2001, 105:10673-10680.
12. Sakota K., Sekiya H. J. Phys. Chem. A 2005, 109:2722-2727.
13. Bisht P.B., Okamoto M., Hirayama S. J. Phys. Chem. B 1997, 101:8850-8855.
14. Chen K.-Y., Hsieh C.-C., Lai C.-H., Chou P.-T. Chem. Commun. 2006, 4395-4397.
15. Catalan J., Perez P., del Valle J.C., de Paz J.L.G., Kasha M. Proc. Natl. Acad. Sci. USA 2002, 99:5793-5798.
16. Catalan J., Perez P., del Valle J.C., de Paz J.L.G., Kasha M. Proc. Natl. Acad. Sci. USA 2002, 99:5799-5803.
17. Herek J.L., Pedersen S., Banares L., Zewail A.H. J. Chem. Phys. 1992, 97:9046-9061.
18. Sobolewski A.L., Domcke W. Chem. Chem. Phys. 2006, 8:3410-3417.
19. Catalan J., del Valle J.C. J. Am. Chem. Soc. 1993, 115:4321-4325.
20. Mohammed O.F., Pines D., Nibbering E.T.J., Pines E. Angew. Chem. Int. Ed. 2007, 46:1458-1461.
21. Heller H.J., Blattmann H.R. Pure Appl. Chem. 1974, 36:141-162.
22. Ferrer M.L., Acuña A.U., Amat-Guerri F., Costela A., Figuera J.M., Florido F., Sastre R. Appl. Opt. 1994, 33:2266-2272.
23. Chou P.-T., MxMorrow D., Aartsna T.J., Kasha M. J. Phys. Chem. 1984, 88:4596-4599.
24. Lim J.S., Seo J., Park S.Y. J. Am. Chem. Soc. 2006, 128:14542-14547.
25. Paul B.K., Samanta A., Guchhait N. Langmuir 2010, 26:3214-3224.
26. Paul B.K., Guchhait N. J. Phys. Chem. B 2010, 114:12528-12540.
27. Paul B.K., Guchhait N. J. Colloid Interf. Sci. 2011, 353:237-247.
28. Chowdhury P., Chakravorti S. Chem. Phys. Lett. 2004, 395:103-108.
29. Sahu K., Roy D., Mondal S.K., Karmakar R., Bhattacharyya K. Chem. Phys. Lett. 2005, 404:341-345.
30. Sutton S., Campbell N.L., Cooper A.I., Kirkl M., Frith W.J., Adams D.J. Langmuir 2009, 25:10285-10291.
31. Organero J.A., Moreno M., Santos L., Lluch J.M., Douhal A. J. Phys. Chem. A 2000, 104:8424-8431.
32. Kyrychenko A., Herbich J., Izydorzak M., Wu F., Thummel R.P., Waluk J. J. Am. Chem. Soc. 1999, 121:11179-11188.
33. Herbich J., Kijak M., Zielin'ska A., Thummel R.P., Waluk J. J. Phys. Chem. A 2002, 106:2158-2163.
34. Yu W.-S., Cheng C.-C., Cheng Y.-M., Wu P.-C., Song Y.-H., Chi Y., Chou P.-T. J. Am. Chem. Soc. 2003, 125:10800-10801.
35. Cao Y., Varo G., Chang M., Ni B., Needleman R., Lanyi J.K. Biochemistry 1991, 30:10972-10979.
36. Jasien P.G., Stevens W.J. J. Chem. Phys. 1986, 84:3271-3278.
37. Bell R.L., Truong T.N. J. Chem. Phys. 1994, 101:10442-10452.
38. Gaussian 03, M.J. Frisch, et al. Gaussian, Inc., Pittsburgh, PA, 2003.
39. Cossi M., Barone V., Mennucci B., Tomasi J. Chem. Phys. Lett. 1998, 286:253-260.
40. Mennucci B., Tomasi J. J. Chem. Phys. 1997, 106:5151-5159.
41. Boys S.F., Bernardi F. Mol. Phys. 1970, 19:553-566.
42. Khaliullin R., Bell A.T., Head-Gordon M. Chem. Eur. J. 2009, 15:851-855.
43. Reed A.E., Curtiss L.A., Weinhold F.A. Chem. Rev. 1988, 88:899-926.
44. E.D. Glendening, A.E. Reed, J.E. Carpenter, F.A. Weinhold, NBO, Version 3.1, 1995.
45. Hobza P., Havlas Z. Chem. Rev. 2000, 100:4253-4264.
46. Chakraborty A., De R., Guchhait N. Chem. Phys. Lett. 2006, 432:616-622.
47. Casida M.E., Jamorski C., Casida K.C., Salahub D.R. J. Chem. Phys. 1998, 108:4439-4450.
48. Stratmann R.E., Scuseria G.E., Frisch M.J. J. Chem. Phys. 1998, 109:8218-8225.
49. Maheshwary S., Chowdhury A., Sathyamurthy N., Mishra H., Tripathi H.B., Panda M., Chandrasekhar J. J. Phys. Chem. A 1999, 103:6257-6262.
50. Mahanta S., Paul B.K., Singh R.B., Guchhait N. J. Comput. Chem. 2011, 32:1-14.
51. Mishra H., Maheshwary S., Tripathi H.B., Sathyamurthy N. J. Phys. Chem. A. 2005, 109:2746-2754.
52. Paul B.K., Mahanta S., Singh R.B., Guchhait N. J. Phys. Chem. A 2010, 114:2618-2627.
53. Picazo O., Alkorta I., Elguero J. J. Org. Chem. 2003, 68:7485-7489.
54. Desiraju G., Steiner T. The Weak Hydrogen Bond: In Structural Chemistry and Biology 1999, Oxford University Press, New York.
55. Zhao G.-J., Han K.-L. Biophys. J. 2008, 94:38-46. (and references therein).
56. Bell R.L., Taveras D.L., Truong T.N., Simons J. Int. J. Quantum Chem. 1997, 63:861-874.
57. Zhao X., Chen M. J. Phys. Chem. A 2010, 114:7786-7790. (and references therein).
58. Berg J.M., Tymoczko J.L., Stryer L. Biochemistry 2002, W.H. Freeman and Company, New York. fifth ed. T.M. Devlin (Ed.).
59. Watson J.D., Crick F.H.C. Nature 1953, 171:964-967.
60. Nagaoka S., Nakamura A., Nagashima U. J. Photochem. Photobiol. A: Chem. 2002, 154:23-32. (and references therein).
61. Bent H.A. Chem. Rev. 1961, 61:275-311.