A DFT study on the standard electrode potentials of 2-substituted imidazoles

International Journal of Quantum Chemistry

Volumn 113, Issue 5, 2013, Pages 715-722

  Tugsuz, Tugba ^a  

^a HACETTEPE UNIVERSITY   (Turkey)

Author keywords

2 substituted imidazoles; BMK; CPCM; DFT; M05; standard electrode potentials; TZVP

Indexed keywords

2-SUBSTITUTED IMIDAZOLES; BMK; CPCM; DFT; M05; STANDARD ELECTRODE POTENTIAL; TZVP;

ACETONITRILE; CONTINUUM MECHANICS; DENSITY FUNCTIONAL THEORY; ELECTRONS; GEOMETRY; OPTIMIZATION; ORGANIC SOLVENTS; POSITIVE IONS; PROTONATION;

PLANTS (BOTANY);

EID: 84873077782     PISSN: 00207608     EISSN: 1097461X     Source Type: Journal    
DOI: 10.1002/qua.24055     Document Type: Conference Paper

References (62)

1. (a), D. Middlemiss, S. P. Watson, Tetrahedron 1994, 50, 13049-13080
2. (b), J. C. Bohem, J. G. Gleason, I. Pendrak, H. M. Sarau, D. B. Schmidt, J. J. Foley, W. D. Kingsbury, J. Med. Chem. 1993, 36, 3333-3340
3. (c), R. P. Walker, D. J. Faulkner, D. Van Engen, J. Clardy, J. Am. Chem. Soc. 1981, 103, 6772-6773
4. (d), T. P. Holler, F. Ruan, A. Spaltenstein, P. B. Hopkins, J. Org. Chem. 1989, 54, 4570-4575
5. (e), P. R. Lowe, C. E. Sansom, C. H. Schwalbe, M. F. G. Stevens, A. S. Clark, J. Med. Chem. 1992, 35, 3377-3382
6. (f), A. Commercon, J. M. Paris, Tetrahedron Lett. 1991, 32, 4905-4906
7. (g), A. A. Hagedorn, III, P. W. Erhardt, W. C. Luma, R. A. Wohl, E. Cantor, Y.-L. Chou, W. R. Ingebretsen, J. W. Lampe, D. Pang, C. A. Pease, J. Wiggins, J. Med. Chem. 1987, 30, 1342-1347
8. (h), S. Carmely, M. Ilan, Y. Kashman, Tetrahedron 1989, 45, 2193-2200
9. (i), D. J. K. Crawford, J. L. Maddocks, D. N. Jones, P. Szawlowski, J. Med. Chem. 1996, 39, 2690-2695
10. (j), H. Tomioka, T. Yano, Y. Takeda, H. Takeda, N. Hirata, Agric. Biol. Chem. 1991, 55, 1601-1606
11. (k), A. Thurkauf, J. Yuan, X. Chen, X. S. He, J. W. F. Wasley, A. Hutchison, K. H. Woodruff, R. Meade, D. C. Hoffman, H. Donovan, D. K. Hohnes-Hertzog, J. Med. Chem. 1997, 40, 1-3
12. (l), A. G. Chittiboyina, Ch. R. Reddy, E. B. Watkins, M. A. Avery, Tetrahedron Lett. 2004, 45, 1869-1872.
13. (a), S. Mallakpour, Z. Rafiee, J. Polym. Environ. 2011, 19, 447-484
14. (b), Z. Wang, W. Bao, Y. Jiang, Chem. Commun. 2005, 22, 2849-2851
15. (c), L. Niedzicki, M. Kasprzyka, K. Kuziaka, G. Z. Zukowskaa, M. Marcineka, W. Wieczoreka, M. Armand, J. Power Sources 2011, 196, 1386-1391
16. (d), J. Scheers, P. Johansson, P. Szczecinski, W. Wieczorek, M. Armand, P. Jacobsson, J. Power Sources 2010, 195, 6081-6087
17. (e), K. Binnemans, Chem. Rev. 2005, 105, 4148-4204
18. (f), E. B. Anderson, T. E. Long, Polymer 2010, 51, 2447-2454.
19. (a), W. W. Bachovchin, Biochemistry 1986, 25, 7751-7759
20. (b), T. Noguchi, Y. Inoue, X. S. Tang, Biochemistry 1999, 38, 399-403
21. (c), M. Sorlie, J. Christiansen, B. J. Lemon, J. W. Peters, D. R. Dean, B. J. Hales, Biochemistry 2001, 40, 1540-1549.
22. (a), M. L. Bender, R. J. Bergeron, M. Komiyama, In The Bioorganic Chemistry of Enzymatic Catalysis; Wiley-Interscience: New York, 1984
23. (b), R. Stewart, The Proton: Applications to Organic Chemistry; Academic Press: Orlando FL, 1985.
24. D. M. Blow, Acc. Chem. Res. 1976, 9, 145-152.
25. (a), R. K. McMullan, J. Epstein, J. R. Ruble, B. M. Craven, Acta Crystallogr. 1979, B35, 688-691
26. (b), B. M. Craven, R. K. McMullan, J. D. Bell, H. C. Freeman, Acta Crystallogr. 1977, B33, 2585-2589.
27. N. Ö. Pekmez, M. Can, A. Yildiz, Acta Chim. Slov 2007, 54, 131-139.
28. F. Veyisoglu, M. Şahin, N. Ö. Pekmez, M. Can, A. Yildiz, Acta Chim. Slov 2004, 51, 483-494.
29. J. L. Brédas, M. P. Poskin, J. Delhalle, J. M. André, H. Chojnacki, J. Phys. Chem. 1984, 88, 5882-5887.
30. M. Tafazzoli, S. K. Amini, Chem. Phys. Lett. 2006, 431, 421-427.
31. B. H. Kipp, C. Faraj, G. Li, D. Njus, Bioelectrochemistry 2004, 64, 7-13.
32. (a), M. Namazian, H. A. Almodarresieh, J. Mol. Struct.: (THEOCHEM) 2004, 686, 97-102
33. (b), M. Namazian, H. A. Almodarresieh, M. R. Noorbala, H. R. Zare, Chem. Phys. Lett. 2004, 396, 424-428
34. (c), M. Namazian, H. R. Zare, M. L. Coote, Biophys. Chem. 2008, 132, 64-68
35. (d), C. P. Kelly, C. J. Cramer, D. G. Truhlar, J. Phys. Chem. B 2007, 111, 408-422
36. (e), Y. Song, J. F. Zhou, Y. Song, Y. Wei, H. Wang, Bioorg. Med. Chem. Lett. 2005, 15, 4971-4975
37. (f), Y. Song, Spectrochim. Acta Part A 2007, 67, 611-618
38. (g), A. L. Speelman, J. G. Gillmore, J. Phys. Chem. A 2008, 112, 5684-5690
39. (h), S. N. Datta, J. Sudhamsu, A. Pandey, J. Phys. Chem. B 2004, 108, 8007-8016
40. (i), S. Riahi, M. R. Ganjali, A. B. Moghaddam, P. Norouzi, M. Niasari, J. Mol. Struct.: (THEOCHEM) 2006, 774, 107-111
41. (j), M. Shamsipur, A. Siroueinejad, B. Hemmateenejad, A. Abbaspour, H. Sharghi, K. Alizadeh, S. Arshadi, J. Electroanal. Chem. 2007, 600, 345-358.
42. (a), C. J. Cramer, Essentials of Computational Chemistry: Theories and Models, 2nd ed.; John Wiley: Chichester, 2007
43. (b), M.-H. Baik, R. A. Friesner, J. Phys. Chem. A 2002, 106, 7407-7412
44. (c), M. Schmidt am Busch, E.-W. Knapp, J. Am. Chem. Soc. 2005, 127, 15730-15737
45. (d), P. Winget, E. J. Weber, C. J. Cramer, D. G. Truhlar, Phys. Chem.Chem. Phys. 2000, 2, 1231-1239.
46. (a), P. Hohenberg, W. Kohn, Phys. Rev. 1964, 136, B864-B871
47. (b), W. Kohn, L. Sham, J. Phys. Rev. 1965, 140, A1133-A1138
48. (c), A. K. Theophilou, J. Phys. C: Solid State Phys. 1979, 12, 5419-5430
49. (d), N. Hadjisavvas, A. K. Theophilou, Phys. Rev. A 1984, 30, 2183-2186.
50. Y. Zhao, D. G. Truhlar, Acc. Chem. Res. 2008, 41, 157-167.
51. T. Tugsuz, J. Phys. Chem. B 2010, 114, 17092-17101.
52. M. D. Liptak, K. C. Gross, P. G. Seybold, S. Feldgus, G. C. Shields, J. Am. Chem. Soc. 2002, 124, 6421-6427
53. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, J. E. Peralta, Jr., F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, 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, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian 09, revision A.02, Gaussian, Inc., Wallingford CT, 2009.
54. A. D. Boese, J. M. L. Martin, J. Chem. Phys. 2004, 121, 3405-3416.
55. Y. Zhao, N. E. Schultz, D. G. Truhlar, J. Chem. Phys. 2005, 123, 161103, 1- 4.
56. A. Schaefer, C. Huber, R. Ahlrichs, J. Chem. Phys. 1994, 100, 5829-5835.
57. (a), V. Barone, M. Cossi,. J. Phys. Chem. A 1998, 102, 1995-2001
58. (b), M. Cossi, N. Rega, G. Scalmani, V. Barone, J. Comp. Chem. 2003, 24, 669-681.
59. A. Cammers, S. Parkin, CrystEngComm. 2004, 6, 168-172.
60. W. Tatara, M. J. Wojcik, J. Phys. Chem. A 2003, 107, 7827-7831.
61. S. Yan, Y. Bu, J. Chem. Phys. 2005, 122, 184324, 1- 8.
62. H. Strehlow, In The Chemistry of Nonaqueous Solvents, J. J. Lagowski, Ed.; Academic Press: New York, 1966.