Theoretical studies of the solvent effect on conformational equilibria and atomic charges for isolated and hydrogen-bonded dimethoxy thiadiazoles

Computational and Theoretical Chemistry

Volumn 966, Issue 1-3, 2011, Pages 194-206

  Nagy, Peter I ^a   Tejada, Frederick R ^b,c   Kim, Yong Wah ^a   Messer Jr , William S ^a,b  

^a UNIVERSITY OF TOLEDO   (United States)

^b MEDICAL COLLEGE OF OHIO   (United States)

^c UNIVERSITY OF MARYLAND EASTERN SHORE   (United States)

Author keywords

Atomic charges; Charge transfer; Conformational equilibria; Dimethoxy thiadiazoles; Monte Carlo simulations; PCM

Indexed keywords

EID: 84962338763     PISSN: 2210271X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.comptc.2011.02.034     Document Type: Article

References (70)

1. G. Rauhut, in: A.R. Katritzky (Ed.), Advances in Heterocyclic Chemistry, vol. 81, Academic Press, San Diego, 2001, p. 1.
2. M.K. Shukla, J. Leszczynski, J. Phys. Chem. A 106 (2002) 11338.
3. P.I. Nagy, F.R. Tejada, W.S. Messer Jr., J. Phys. Chem. B 109 (2005) 22588.
4. M. Kabelac, P. Hobza, J. Phys. Chem. B 110 (2006) 14515.
5. M.K. Shukla, J. Leszczynski, Chem. Phys. Lett. 429 (2006) 261.
6. J. Rejnek, P. Hobza, J. Phys. Chem. B 111 (2007) 641.
7. P.I. Nagy, A. Maheshwari, Y.-W. Kim, W.S. Messer Jr., J. Phys. Chem. B 114 (2010) 349.
8. P. Sauerberg, P.H. Olesen, S. Nielsen, S. Treppendahl, M.J. Sheardown, T. Honore, C.H. Mitch, J.S. Ward, A.J. Pike, F.P. Bymaster, B.D. Sawyer, H.E. Shannon, J. Med. Chem. 35 (1992) 2274.
9. W.G. Rajeswaran, Y. Cao, X.P. Huang, M.E. Wroblewski, T. Colclough, S. Lee, F. Liu, P.I. Nagy, J. Ellis, B.A. Levine, K.H. Nocka, W.S. Messer Jr., J. Med. Chem. 44 (2001) 4563.
10. Y. Cao, M. Zhang, C. Wu, S. Lee, E. Wroblewski, T. Whipple, P.I. Nagy, K. Takacs-Novak, A. Balazs, S. Toros, W.S. Messer Jr., J. Med. Chem. 46 (2003) 4273.
11. F.R. Tejada, P.I. Nagy, M. Xu, C. Wu, T. Katz, J. Dorsey, M. Rieman, E. Lawlor, M. Warrier, W.S. Messer Jr., J. Med. Chem. 49 (2006) 7518.
12. T. Pasinszki, M. Krebsz, G.J. Vass, J. Mol. Struct. 966 (2010) 85. and references therein.
13. G. Alagona, C. Ghio, P.I. Nagy, J. Chem. Theory Comput. 1 (2005) 801.
14. P.I. Nagy, W.M.F. Fabian, J. Phys. Chem. B 110 (2006) 25026.
15. P.I. Nagy, G. Alagona, C. Ghio, J. Chem. Theory Comput. 3 (2007) 1249
16. P.I. Nagy, M.R. Dhananjeyan, P.W. Erhardt, J. Mol. Struct. THEOCHEM 895 (2009) 116.
17. Gaussian 03, Revision C.02: M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., T. Vreven, K. 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, J.A. Pople, Gaussian, Inc., Wallingford CT, 2004.
18. O.L. Stiefvater, Chem. Phys. 13 (1976) 73.
19. L. Nygaard, R.L. Hansen, G.O. Sørensen, J. Mol. Struct. 9 (1971) 163.
20. B. Bak, D. Christensen, L. Hansen-Nygaard, L. Lipshitz, J. Rastrup-Andersen, J. Mol. Spectrosc. 9 (1962) 225.
21. O.L. Stiefvater, Z. Naturforsch. 31a (1976) 1681.
22. A.R. Katritzky, Physical Methods in Heterocyclic Chemistry, vol. VI, Academic Press, New York, 1974.
23. O.L. Stiefvater, Z. Naturforsch. 33a (1978) 1511.
24. V. Dobyns, L. Pierce, J. Am. Chem. Soc. 85 (1963) 3553.
25. A.A. El-Azhary, Acta Chem. Scand. 49 (1995) 11-19.
26. A.A. El-Azhary, Spectrochim. Acta 51A (1995) 995-1003.
27. N.E. Kassimi, Z. Lin, J. Phys. Chem. A 102 (1998) 9906.
28. D.J. Glossman-Mitnik, J. Mol. Struct. THEOCHEM 725 (2005) 27.
29. A.D. Becke, J. Chem. Phys. 98 (1993) 5648.
30. C. Lee, W. Yang, R.G. Parr, Phys. Rev. B 37 (1988) 785.
31. C. Adamo, V. Barone, J. Chem. Phys. 108 (1998) 664.
32. W.J. Hehre, L. Radom, P.V.R. Schleyer, J.A. Pople, Ab Initio Molecular Orbital Theory, Wiley, New York, 1986.
33. C. Møller, M.S. Plesset, Phys. Rev. 46 (1934) 618.
34. J.A. Pople, J.S. Binkley, R. Seeger, Int. J. Quantum Chem. 10s (1976) 1.
35. R. Krishnan, M.J. Frisch, J.A. Pople, J. Chem. Phys. 72 (1980) 4244.
36. J.A. Pople, M. Head-Gordon, K. Raghavachari, J. Chem. Phys. 87 (1987) 5968.
37. R.A. Kendall, T.H. Dunning Jr., R.J. Harrison, J. Chem. Phys. 96 (1992) 6796.
38. D.E. Woon, T.H. Dunning Jr., J. Chem. Phys. 100 (1994) 2975.
39. K.A. Peterson, Annu. Rep. Comput. Chem. 3 (2007) 195.
40. T.H. Dunning Jr., K.A. Peterson, A.K. Wilson, J. Chem. Phys. 114 (2001) 9244.
41. S. Miertus, E. Scrocco, J. Tomasi, Chem. Phys. 55 (1981) 117.
42. S. Miertus, J. Tomasi, Chem. Phys. 65 (1982) 239.
43. J. Tomasi, M. Persico, Chem. Rev. 94 (1994) 2027.
44. J. Tomasi, B. Mennucci, R. Cammi, Chem. Rev. 105 (2005) 2999.
45. A. Bondi, J. Phys. Chem. 68 (1964) 441.
46. D.R. Lide (Ed.), CRC Handbook of Chemistry and Physics, 88th ed., CRC Press Taylor and Francis Group, Boca Raton, FL, 2007.
47. D.A. McQuarrie, Statistical Mechanics, University Science Books, Sausalito, CA, 2000.
48. W.L. Jorgensen, J.D. Madura, J. Am. Chem. Soc. 105 (1983) 1407.
49. W.L. Jorgensen, C.J. Swenson, J. Am. Chem. Soc. 107 (1985) 1489.
50. W.L. Jorgensen, J. Gao, J. Phys. Chem. 90 (1986) 2174.
51. W.L. Jorgensen, J.M. Briggs, M.L. Contreras, J. Phys. Chem. 94 (1990) 1683.
52. W.L. Jorgensen, W.L. BOSS, Version 4.7; Biochemical and Organic Simulation System User's Manual, Yale University, New Haven, CT, 2006.
53. W.L. Jorgensen, D.S. Maxwell, J. Tirado-Rives, J. Am. Chem. Soc. 118 (1996) 11225.
54. R.C. Rizzo, W.L. Jorgensen, J. Am. Chem. Soc. 121 (1999) 4827.
55. C.M. Breneman, K.B. Wiberg, J. Comput. Chem. 11 (1990) 361.
56. J.M. Briggs, T. Matsui, W.L. Jorgensen, J. Comput. Chem. 11 (1990) 958.
57. P.P. Ewald, Ann. Phys. 369 (1921) 253.
58. M.P. Allen, D. Tildesley, Computer Simulations of Liquids, Oxford University Press, Oxford, UK, 1987.
59. R.W. Zwanzig, J. Chem. Phys. 22 (1952) 1420.
60. W.L. Jorgensen, C. Ravimohan, J. Chem. Phys. 83 (1985) 3050.
61. P.I. Nagy, P.W. Erhardt, J. Phys. Chem. A 110 (2006) 13923.
62. P.I. Nagy, F.R. Tejada, J.G. Sarver, W.S. Messer Jr., J. Phys. Chem. A 108 (2004) 10174.
63. S. Melandri, A. Maris, Phys. Chem. Chem. Phys. 6 (2004) 2863.
64. P.I. Nagy, G. Völgyi, K. Takács-Novák, Mol. Phys. 103 (2005) 1589.
65. L. Lunazzi, F. Parisi, D. Macciantelli, J. Chem. Soc., Perkin Trans. 2 (1993) 1025.
66. Y. Duan, C. Wu, S. Chowdhury, M.C. Lee, G. Xiong, W. Zhang, R. Yang, P. Cieplak, R. Luo, T. Lee, J. Caldwell, J. Wang, P.A. Kollman, J. Comput. Chem. 24 (2003) 1999.
67. P.I. Nagy, P.I. P.W. Erhardt, J. Phys. Chem. B 114 (2010) 16436.
68. P.I. Nagy, G.J. Durant, D.A. Smith, J. Am. Chem. Soc. 115 (1993) 2912.
69. P.I. Nagy, K. Takács-Novák, Phys. Chem. Chem. Phys. 6 (2004) 2838.
70. S.J. Grabowski, Annu. Rep. Prog. Chem., Sect. C 102 (2006) 131.