Role of nitrogen substitution in phenyl ring on excited state intramolecular proton transfer and rotamerism of 2-(2′-hydroxyphenyl) benzimidazole: A theoretical study

Journal of Chemical Physics

Volumn 134, Issue 10, 2011, Pages

  Chipem, Francis A S ^a   Dash, Nihar ^a   Krishnamoorthy, G ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY GUWAHATI   (India)

Author keywords

[No Author keywords available]

Indexed keywords

DENSITY FUNCTIONAL THEORY; GROUND STATE; ION EXCHANGE; MOLECULES; NITROGEN; PHENOLS; PROTON TRANSFER;

BENZIMIDAZOLES; COMPARATIVE STUDIES; COMPUTATIONAL RESULTS; CONFIGURATION INTERACTION SINGLES; EMISSION ENERGIES; EXCITED SINGLET STATE; EXCITED-STATE INTRAMOLECULAR PROTON TRANSFER; EXPERIMENTAL DATA; INTERCONVERSIONS; INTRAMOLECULAR PROTON TRANSFER; PHENOLIC RINGS; PHENYL RINGS; PHOTOPHYSICS; PYRIDYL; STABLE FORM; THEORETICAL STUDY; TIME-DEPENDENT DFT; WATER MOLECULE;

EXCITED STATES;

BENZIMIDAZOLE DERIVATIVE; NITROGEN; PROTON; WATER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMPARATIVE STUDY; HYDROGEN BOND;

BENZIMIDAZOLES; HYDROGEN BONDING; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NITROGEN; PROTONS; WATER;

EID: 79952656789     PISSN: 00219606     EISSN: None     Source Type: Journal    
DOI: 10.1063/1.3562124     Document Type: Article

References (59)

1. K. Faxén, G. Gilderson, P. delroth, and P. Brzezinski, Nature (London) 437, 286 (2005). 10.1038/nature03921 (Pubitemid 41294494)
2. A. Douhal, S. K. Kim, and A. H. Zewail, Nature (London) 378, 260 (1995). 10.1038/378260a0
3. M. Kasha, J. Chem. Soc., Faraday Trans. 2 82, 2379 (1986). 10.1039/F29868202379
4. S. J. Formosinho and L. G. Arnaut, J. Photochem. Photobiol., A 75, 21 (1993). 10.1016/1010-6030(93)80158-6
5. Y. Wu, X. Peng, J. Fan, S. Gao, M. Tian, J. Zhao, and S. Sun, J. Org. Chem. 72, 62 (2007). 10.1021/jo061634c (Pubitemid 46068204)
6. M. S. Celej, W. Caarls, A. P. Demchenko, and T. M. Jovin, Biochemistry 48, 7465 (2009). 10.1021/bi9003843
7. P. Chou, D. McMorrow, T. J. Aartsma, and M. Kasha, J. Phys. Chem. 88, 4596 (1984). 10.1021/j150664a032
8. G. Zhang, H. Wang, Y. Yu, F. Xiong, G. Tang, and W. Chen, Appl. Phys. B 76, 677 (2003). 10.1007/s00340-003-1164-0
9. S. Kumar, V. Luxami, R. Saini, and D. Kaur, Chem. Commun. (Cambridge) 2009, 3044. 10.1039/b900131j
10. M. J. Paterson, M. A. Robb, L. Blancafort, and A. D. DeBellis, J. Phys. Chem. A 109, 7527 (2005). 10.1021/jp051108+ (Pubitemid 41321593)
11. A. Ohshima, A. Momotake, R. Nagahata, and T. Arai, J. Phys. Chem. A 109, 9731 (2005). 10.1021/jp053702p (Pubitemid 41609700)
12. R. Vivie-Riedle, V. De Vaele, L. Kurtz, and E. Riedle, J. Phys. Chem. A 107, 10591 (2003). 10.1021/jp035204r
13. M. Mosquera, J. C. Penedo, M. C. R. Ros Rodrguez, and F. Rodrguez-Prieto, J. Phys. Chem. 100, 5398 (1996). 10.1021/jp9533638
14. A. Pla-Dalmau, J. Org. Chem. 60, 5468 (1995). 10.1021/jo00122a027
15. P. Purkayastha and N. Chattopadhyay, Phys. Chem. Chem. Phys. 2, 203 (2000). 10.1039/a908359f
16. H. E. A. Kramer, in Photochromism: Molecules and Systems, 1st ed., edited by, H. Drr, and, H. Bouas-Laurent, (Elsevier, Amsterdam, 1990), Chap. 16, pp. 645-684.
17. M. J. Paterson, M. A. Robb, L. Blancafort, and A. D. DeBellis, J. Am. Chem. Soc. 126, 2912 (2004). 10.1021/ja0386593 (Pubitemid 38314297)
18. A. K. Ogawa, O. K. Abou-Zied, V. Tsui, R. Jimenez, D. A. Case, and F. E. Romesberg, J. Am. Chem. Soc. 122, 9917 (2000). 10.1021/ja001778n
19. F. Y. Dupradeau, D. A. Case, C. Yu, R. Jimenez, and F. E. Romesberg, J. Am. Chem. Soc. 127, 15612 (2005). 10.1021/ja054607x (Pubitemid 41572535)
20. C. E. Fellows, E. Tuber, C. C. Rodegheri, C. E. M. Carvalho, D. F. Acevedo, S. G. Bertolotti, and C. Barbero, Opt. Mater. 27, 499 (2004). 10.1016/j.optmat.2004.04.011
21. S. Hillebrand, M. Segala, T. Buckup, R. R. B. Correia, F. Horowitz, and V. Stefani, Chem. Phys. 273, 1 (2001). 10.1016/S0301-0104(01)00469-4
22. S. M. Chang, K. L. Hsueh, B. K. Huang, J. H. Wu, C. C. Liao, and K. C. Lin, Surf. Coat. Technol. 200, 3278 (2006). 10.1016/j.surfcoat.2005.07.060 (Pubitemid 43169081)
23. S. K. Das and S. K. Dogra, J. Chem. Soc., Faraday Trans. 94, 139 (1998). 10.1039/a703656f
24. T.-I. Kim, H. J. Kang, G. Han, S. J. Chung, and Y. Kim, Chem. Commun. (Cambridge) 2009, 5895. 10.1039/b911145j
25. H. K. Sinha and S. K. Dogra, Chem. Phys. 102, 337 (1986). 10.1016/0301-0104(86)80006-4
26. M. M. Balamurali and S. K. Dogra, J. Photochem. Photobiol., A 154, 81 (2002). 10.1016/S1010-6030(02)00308-8
27. G. Krishnamoorthy and S. K. Dogra, J. Lumin. 92, 91 (2001). 10.1016/S0022-2313(00)00244-1
28. G. Krishnamoorthy and S. K. Dogra, J. Lumin. 92, 103 (2001). 10.1016/S0022-2313(00)00243-X
29. M. Mosquera, M. C. R. Rodrguez, and F. Rodrguez-Prieto, J. Phys. Chem. A 101, 2766 (1997). 10.1021/jp9626834
30. M. C. R. Rodrguez, M. Mosquera, and F. Rodrguez-Prieto, J. Phys. Chem. A 105, 10249 (2001). 10.1021/jp010053i (Pubitemid 35378457)
31. S. K. Dogra, J. Mol. Struct. 734, 51 (2005). 10.1016/j.molstruc.2004.08. 025 (Pubitemid 39647275)
32. F. A. S. Chipem and G. Krishnamoorthy, J. Phys. Chem. A 113, 12063 (2009). 10.1021/jp903535g
33. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, T. Vreven Jr., K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, and J. A. Pople, GAUSSIAN 03, Revision E.01, Gaussian, Inc., Wallingford, CT, 2004.
34. P. Hohenberg and W. Kohn, Phys. Rev. 136, B864 (1964). 10.1103/PhysRev.136.B864
35. W. Kohn and L. J. Sham, Phys. Rev. 140, A1133 (1965). 10.1103/PhysRev.140.A1133
36. A. D. Becke, J. Chem. Phys. 98, 5648 (1993). 10.1063/1.464913
37. C. Lee, W. Yang, and R. G. Parr, Phys. Rev. B 37, 785 (1988). 10.1103/PhysRevB.37.785
38. M. E. Casida, in Recent Advances in Density Functional Methods, Part I, edited by, D. P. Chong, (World Scientific, Singapore, 1995), Chap. 5, pp. 155-192.
39. E. Gross, J. Dobson, and M. Petersilka, Top. Curr. Chem. 181, 81 (1996). 10.1007/BFb0016641
40. G.-J. Zhao and K.-L. Han, J. Phys. Chem. A 113, 14329 (2009). 10.1021/jp903200x
41. R. Casadess, M. Moreno, and J. M. Lluch, J. Photochem. Photobiol., A 173, 365 (2005). 10.1016/j.jphotochem.2005.04.016 (Pubitemid 40935812)
42. Z. Yang, S. Yang, and J. Zhang, J. Phys. Chem. A 111, 6354 (2007). 10.1021/jp068589x (Pubitemid 47184338)
43. J. B. Foresman, M. Head-Gordon, J. A. Pople, and M. J. Frisch, J. Phys. Chem. 96, 135 (1992). 10.1021/j100180a030
44. J. F. Stanton, J. Gauss, N. Ishikawa, and M. Head-Gordon, J. Chem. Phys. 103, 4160 (1995). 10.1063/1.469601
45. K. B. Wiberg, Y.-G. Wang, A. E. de Oliveira, S. A. Perera, and P. H. Vaccaro, J. Phys. Chem. A 109, 466 (2005). 10.1021/jp040558j (Pubitemid 40206804)
46. M. K. Shukla and J. Leszczynski, Int. J. Quantum Chem. 105, 387 (2005). 10.1002/qua.20714 (Pubitemid 43080652)
47. G. Gahungu and J. Zhang, J. Phys. Chem. B 109, 17762 (2005). 10.1021/jp052220a (Pubitemid 41396228)
48. M. Bellette, N. Blouin, P.-L. T. Boudreault, M. Leclerc, and G. Durocher, J. Phys. Chem. A 110, 13696 (2006). 10.1021/jp066143a (Pubitemid 46133383)
49. F. A. S. Chipem, S. Chatterjee, and G. Krishnamoorthy, J. Photochem. Photobiol., A 214, 121 (2010). 10.1016/j.jphotochem.2010.06.014
50. C. Jamorski, J. B. Foresman, C. Thilgen, and H.-P. Lthi, J. Chem. Phys. 116, 8761 (2002). 10.1063/1.1465404 (Pubitemid 34631423)
51. S. Miertu, E. Scrocco, and J. Tomasi, Chem. Phys. 55, 117 (1981). 10.1016/0301-0104(81)85090-2
52. E. Cancs, B. Mennucci, and J. Tomasi, J. Chem. Phys. 107, 3032 (1997). 10.1063/1.474659
53. See supplementary material at http://dx.doi.org/10.1063/1.3562124 E-JCPSA6-134-027109 for the additional tables related to structural parameters of optimized geometries as well as their corresponding dipole moments and solvent effects on intramolecular proton transfer and S1-S0 energy gap of twisted keto. Reaction scheme on water assisted intermolecular proton transfer and potential energy surface for torsional rotation of keto tautomers are also provided.
54. F. Rodrguez-Prieto, M. C. R. Rodrguez, M. M. González, and M. A. R. Fernndez, J. Phys. Chem. 98, 8666 (1994). 10.1021/j100086a014
55. S. Lochbrunner, A. J. Wurzer, and E. Riedle, J. Phys. Chem. A 107, 10580 (2003). 10.1021/jp035203z
56. A. Migani, L. Blancafort, M. A. Robb, and A. D. DeBellis, J. Am. Chem. Soc. 130, 6932 (2008). 10.1021/ja8013924 (Pubitemid 351770127)
57. S. R. Vzquez, C. R. Rodrguez, M. Mosquera, and F. Rodrguez-Prieto, J. Phys. Chem. A 111, 1814 (2007). 10.1021/jp0653813 (Pubitemid 46543236)
58. C. A. Potter, R. G. Brown, F. Vollmer, and W. Rettig, J. Chem. Soc., Faraday Trans. 90, 59 (1994). 10.1039/ft9949000059
59. D. LeGourriérec, V. Kharlanov, R. G. Brown, and W. Rettig, J. Photochem. Photobiol., A 130, 101 (2000). 10.1016/S1010-6030(99)00206-3