Theoretical studies of the in-solution isomeric protonation of non-aromatic six-member rings with two nitrogens

Journal of Physical Chemistry B

Volumn 115, Issue 16, 2011, Pages 4758-4767

  Nagy, Peter I ^a,b   Messer, William S ^b  

^a UNIVERSITY OF TOLEDO   (United States)

^b MEDICAL COLLEGE OF OHIO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COMPUTER SIMULATION; DICHLOROMETHANE; FREE ENERGY; HYDROGEN; MONTE CARLO METHODS; NITROGEN; PROTONATION;

AQUEOUS SOLUTIONS; C-C BONDS; COUNTERIONS; ELECTROSTATIC EFFECT; ENERGY DISTRIBUTIONS; EWALD SUMMATIONS; EXPERIMENTAL VALUES; FREELY MOVING; GAS-PHASE PROTONATION; HYDROGEN-BOND FORMATION; INTERNAL ENERGIES; MODEL SYSTEM; MONTE CARLO SIMULATION; NITROGEN ATOM; RELATIVE FREE ENERGY; SATURATED RINGS; TEST MOLECULES; THEORETICAL CALCULATIONS; THEORETICAL STUDY;

HYDROGEN BONDS;

EID: 84962374511     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp202241m     Document Type: Article

References (67)

1. Rauhut, G., Recent advances in computing heteroatom-rich five- and six-membered ring systems. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic Press: San Diego, 2001, Vol. 81, pp 1 - 105. (Pubitemid 33805824)
2. Shukla, M. K.; Leszczynski, J. J. Phys. Chem. A 2002, 106, 11338-11346
3. Kabelac, M.; Hobza, P. J. Phys. Chem. B 2006, 110, 14515-14523
4. Shukla, M. K.; Leszczynski, J. Chem. Phys. Lett. 2006, 429, 261-265
5. Nagy, P. I.; Tejada, F. R.; Messer, W. S., Jr. J. Phys. Chem. B 2005, 109, 22588-22602
6. Wei, Y.; Zipse, H. Eur. J. Org. Chem. 2008, 3811-3816
7. Abdalla, S.; Springborg, M. J. Phys. Chem. A 2010, 114, 5823-5829
8. Nagy, P. I.; Noszal., B. J. Phys. Chem. A 2000, 104, 6834-6843
9. Nagy, P. I.; Takács-Novák, K. Phys. Chem. Chem. Phys. 2004, 6, 2838-2848
10. Nagy, P. I.; Fabian, W. M. F. J. Phys. Chem. B 2006, 110, 25026-25032
11. Alagona, G.; Ghio, C.; Nagy, P. I. Phys. Chem. Chem. Phys. 2010, 12, 10173-10188
12. Nagy, P. I.; Maheshwari, A.; Kim, Y.-W.; Messer, W. S., Jr. J. Phys. Chem. B 2010, 114, 349-360
13. Nagy, P. I.; Erhardt, W. P. J. Phys. Chem. B 2010, 114, 16436-16442
14. Nelson, J. M.; Chiller, T. M.; Powers, J. H.; Angulo, F. J. Clin. Infect. Dis. 2007, 44, 977-980
15. Okada, J.; Shimabayashi, M. Chem. Pharm. Bull. 1980, 28, 3310-3314
16. Booth, H.; Lemieux, R. U. Can. J. Chem. 1971, 49, 777-788
17. Jones, R. A. Y.; Katritzky, A. R.; Richards, A. C.; Saba, S.; Sparrow, A. J.; Trepanier, D. L. J. Chem. Soc. Chem. Commun. 1972, 673-674
18. Cook, M. J.; Jones, R. A. Y.; Katritzky, A. R.; Manas, M. M.; Richards, A. C.; Sparrow, A. J.; Trepanier, D. L. J. Chem. Soc. Perkin II 1973, 325-331
19. Nelsen, S. F.; Clennan, E. L. J. A. Chem. Soc. 1978, 100, 4004-4012
20. Schweig, A.; Thon, N.; Nelsen, S. F.; Grezzo, L. A. J. Am. Chem. Soc. 1980, 102, 7438-7441
21. Nelsen, S. F.; Kinlen, P. J.; Evans, D. H. J. Am. Chem. Soc. 1981, 103, 7045-7050
22. Nelsen, S. F.; Rumack, D. T.; Sieck, L. W.; Meot-Ner (Mautner), M. J. Am. Chem. Soc. 1988, 110, 6303-6308
23. Pinchas, A.; Schleifer, L.; Fuchs, B.; Wolfe, S. J. Comput. Chem. 1989, 10, 265-283
24. Ma, B.; Lii, J.-H.; Chen, K.; Allinger, N. L. J. Phys. Chem. 1996, 100, 11297-11304
25. ACD/Laboratories. Advanced Chemistry Development Software, V11.02; 1994-2010.
26. Moriyasu, M.; Kato, A.; Hashimoto, Y. J. Chem. Soc., Perkin Trans. II 1986, 515-520
27. 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, Revision C.02; Gaussian, Inc.: Wallingford CT, 2004.
28. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
29. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
30. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory, Wiley: New York, 1986.
31. Dunning, T. H., Jr. J. Chem. Phys. 1989, 90, 1007-1023
32. Kendall, R. A.; Dunning, T. H., Jr.; Harrison, R. J. J. Chem. Phys. 1992, 96, 6796-6806
33. Peterson, K. A. Ann. Rep. Comput. Chem. 2007, 3, 195-206
34. Perdew, J. P. Phys. Rev. B 1986, 33, 8822-8824
35. Raghavachari, K.; Trucks, G. W.; Pople, J. A.; Head-Gordon, M. Chem. Phys. Lett. 1989, 157, 479-483
36. Halkier, A.; Koch, H.; Jorgensen, P.; Christiansen, O.; Beck-Nielsen, I. M.; Helgaker, T. Theor. Chem. Acc. 1997, 97, 150-157
37. Wilson, A.; Dunning, T. H., Jr. J. Chem. Phys. 1997, 106, 8718-8726
38. Helgaker, T.; Klopper, W.; Koch, H.; Noga, J. J. Chem. Phys. 1997, 106, 9639-9646
39. McQuarrie, D. A. Statistical Mechanics; University Science Books: Sausalito, CA, 2000.
40. Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, 117-129
41. Tomasi, J.; Persico, M. Chem. Rev. 1994, 94, 2027-2094
42. Cancès, E.; Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 107, 3032-3041
43. Cancès, E.; Mennucci, B. J. Chem. Phys. 1998, 109, 249-259
44. Cancès, E.; Mennucci, B. J. Chem. Phys. 1998, 109, 260-266
45. Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999-3094
46. Bondi, A. J. Phys. Chem. 1964, 68, 441-451
47. Nagy, P. I.; Alagona, G.; Ghio, C. J. Chem. Theory Comput. 2007, 3, 1249-1266
48. Jorgensen, W. L.; Madura, J. D. J. Am. Chem. Soc. 1983, 105, 1407-1413
49. Jorgensen, W. L.; Swenson, C. J. J. Am. Chem. Soc. 1985, 107, 1489-1496
50. Jorgensen, W. L.; Gao, J. J. Phys. Chem. 1986, 90, 2174-2182
51. Jorgensen, W. L.; Briggs, J. M.; Contreras, M. L. J. Phys. Chem. 1990, 94, 1683-1686
52. Jorgensen, W. L. BOSS, Version 4.7; Biochemical and Organic Simulation System User's Manual, Yale University: New Haven, CT, 2006.
53. Jorgensen, W. L.; Chandrasekhar, J.; Madura, J. D.; Impey, R. W.; Klein, M. L. J. Chem. Phys. 1983, 79, 926-935
54. Jorgensen, W. L.; Maxwell, D. S.; Tirado-Rives, J. J. Am. Chem. Soc. 1996, 118, 11225-11236
55. Rizzo, R. C.; Jorgensen, W. L. J. Am. Chem. Soc. 1999, 121, 4827-4836
56. Breneman, C. M.; Wiberg, K. B. J. Comput. Chem. 1990, 11, 361-373
57. Ewald, P. P. Ann. Phys. 1921, 369, 253-287
58. Allen, M. P.; Tildesley, D. Computer Simulations of Liquids; Oxford University Press: Oxford, U.K., 1987.
59. Nagy, P. I.; Völgyi, G.; Takács-Novák, K. J. Phys. Chem. B 2008, 112, 2085-2094
60. Nagy, P. I.; Dhananjeyan, M. R.; Erhardt, P. W. THEOCHEM 2009, 895, 116-126, and references therein
61. CRC Handbook of Chemistry and Physics, 88 th ed.; Lide, D. R., Ed.; CRC Press Taylor and Francis Group: Boca Raton, FL, 2007-2008.
62. Wiberg, K. B.; Clifford, S.; Jorgensen, W. L.; Frisch, M. J. J. Phys. Chem. A 2000, 104, 7625-7628
63. Sadova, N. I.; Slepnev, G. E.; Tarasenko, N. A.; Zenkin, A. A.; Vilkov, L. V.; Shishkov, I. F.; Pankrushev, Yu. A. Zh. Strukt. Khim. 1977, 18, 865-872
64. Russ. J. Struct. Chem. (Engl. Transl.) 1977, 18, 688-694.
65. Sharma, S. D.; Doraiswamy, S. Chem. Phys. Lett. 1976, 41, 192-198
66. Monti, S.; Nagy, P. I. Phys. Chem. Chem. Phys. 2011, 13, 6270-6279
67. Atkins, P. W. Physical Chemistry, third ed.; W. H. Freeman and Company: New York, 1986, pp 235 - 244.