A theoretical evaluation of the pKHB and ΔH HB⊖ hydrogen-bond scales of nitrogen bases

Chemistry - A European Journal

Volumn 14, Issue 34, 2008, Pages 10656-10669

  Besseau, François ^a   Graton, Jérôme ^a   Berthelot, Michel ^a  

^a UNIVERSITÉ DE NANTES   (France)

Author keywords

Density functional calculations; Hydrogen bonds basicity; Nitrogen bases; pKHB scale

Indexed keywords

ACIDS; ENTHALPY; EXPERIMENTS; FLOW INTERACTIONS; HYDROGEN; HYDROGEN BONDS; ISOMERS; MONOMERS; NITROGEN; NITROGEN COMPOUNDS; NONMETALS; POPULATION STATISTICS;

ASSOCIATION EQUILIBRIUMS; B3LYP DENSITY FUNCTIONAL; BASIS SETS; BILINEAR EQUATIONS; BIOLOGICAL SIGNIFICANCES; BOLTZMANN LAWS; BOND INTERACTIONS; COMPLEXATION REACTIONS; DATA SETS; DENSITY FUNCTIONAL CALCULATIONS; DESCRIPTORS; ELECTROSTATIC POTENTIALS; EXTERNAL-; HYDROGEN FLUORIDES; INTERACTION ENERGIES; MONOFUNCTIONAL; NITROGEN ATOMS; PKHB SCALE; POLYAZINES; POLYNITROGEN; THEORETICAL CALCULATIONS; TRAINING SETS;

HYSTERESIS MOTORS;

EID: 56749091433     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200800977     Document Type: Article

References (89)

1. M. D. Joesten, L. J. Schaad, Hydrogen Bonding, Dekker, New York, 1974.
2. M. H. Abraham, P. L. Grellier, D. V. Prior, P. P. Duce, J. J. Morris, P. J. Taylor, J. Chem. Soc. Perkin Trans. 2 1989, 699 - 711.
3. M. H. Abraham, P. L. Grellier, D. V. Prior, J. J. Morris, P. J. Taylor, J. Chem. Soc. Perkin Trans. 2 1990, 521 -529.
4. M. H. Abraham, Chem. Soc. Rev. 1993, 22, 73-83.
5. D. Gurka, R. W. Taft, J. Am. Chem. Soc. 1969, 91, 4794 - 4801.
6. R. W. Taft, D. Gurka, L. Joris, P. von R. Schleyer, J. W. Rakshys, J. Am. Chem. Soc. 1969, 91, 4801 - 4808.
7. E. M. Arnett, L. Joris, E. Mitchell, T. S. S. R. Murty, T. M. Gorrie, P. von R. Schleyer, J. Am. Chem. Soc. 1970, 92, 2365 -2377.
8. L. Joris, J. Mitsky, R. W. Taft, J. Am. Chem. Soc. 1972, 94, 3438 - 3442.
9. J. Mitsky, L. Joris, R. W. Taft, J. Am. Chem. Soc. 1972, 94, 3442 - 3445.
10. V. Arnaud, J.-Y. Le Questel, M. Mathe-Allainmat, J. Lebreton, M. Berthelot, J. Phys. Chem. A 2004, 108, 10740 - 10748.
11. C. Laurence, M. Berthelot, Perspect. Drug Discovery Des. 2000, 18, 39- 60.
12. L. C. Pauling, The Nature of the Chemical Bond and the Structure of Molecules and Crystals: An Introduction to Modern Structural Chemistry, 3rd ed., Cornell University Press, Ithaca, New York, 1960.
13. J. S. Murray, P. Politzer, J. Chem. Res. Synop. 1992, 110 -111.
14. P. W. Kenny, J. Chem. Soc. Perkin Trans. 2 1994, 199 -202.
15. H. Hagelin, J. S. Murray, T. Brinck, M. Berthelot, P. Politzer, Can. J. Chem. 1995, 73, 483 - 488.
16. J. Graton, M. Berthelot, C. Laurence, J. Chem. Soc. Perkin Trans. 2 2001, 2130 - 2135.
17. M. Hennemann, T. Clark, J. Mol. Model. 2002, 8, 95- 101.
18. J.-Y. Le Questel, M. Berthelot, C. Laurence, J. Chem. Soc. Perkin Trans. 2 1997, 2711 - 2717.
19. O. Lamarche, J. A. Platts, Chem. Eur. J. 2002, 8, 457 -466.
20. O. Lamarche, J. A. Platts, Chem. Phys. Lett. 2003, 367, 123 -128.
21. O. Lamarche, J. A. Platts, Phys. Chem. Chem. Phys. 2003, 5, 677 -684.
22. J. Graton, M. Berthelot, F. Besseau, C. Laurence, J. Org. Chem. 2005, 70, 7892 -7901.
23. J. Graton, M. Berthelot, J.-F. Gal, C. Laurence, J. Lebreton, J.-Y. Le Questel, P.-C. Maria, R. Robins, J. Org. Chem. 2003, 68, 8208 - 8221.
24. Gaussian 03, Revision D.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. 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, J. A. Pople, Gaussian, Inc., Wallingford CT, 2004.
25. Spartan 06, Wavefunction, Inc., Irvine, CA (USA).
26. A. D. Becke, Phys. Rev. A 1988, 38, 3098 -3100.
27. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785 - 789.
28. A. L. Llamas-Saiz, C. Foces-Foces, O. Mo, M. Yanez, E. Elguero, J. Elguero, J. Comput. Chem. 1995, 16, 263 - 272.
29. C. W. Bauschlicher, Jr., Chem. Phys. Lett. 1995, 246, 40- 44.
30. P. R. Rablen, J. W. Lockman, W. L. Jorgensen, J. Phys. Chem. A 1998, 102, 3782 -3797.
31. J. E. Del Bene, W. B. Person, K. Szczepaniak, J. Phys. Chem. 1995, 99, 10 705 -10 707.
32. A. P. Scott, L. Radom, J. Phys. Chem. 1996, 100, 16502 -16513.
33. A. Locati, M. Berthelot, M. Evain, J. Lebreton, J.-Y. Le Questel, M. Mathe-Allainmat, A. Planchat, E. Renault, J. Graton, J. Phys. Chem. A 2007, 111, 6397 -6405.
34. V. Arnaud, M. Berthelot, M. Evain, J. Graton, J.-Y. Le Questel, Chem. Eur. J. 2007, 13, 1499 - 1510.
35. J. S. Murray, S. Ranganathan, P. Politzer, J. Org. Chem. 1991, 56, 3734 - 3737.
36. J. S. Murray, T. Brinck, M. E. Grice, P. Politzer, THEOCHEM 1992, 256, 29 -45.
37. J.-Y. Le Questel, M. Berthelot, C. Laurence, J. Phys. Org. Chem. 2000, 13, 347 -358.
38. J. Graton, F. Besseau, M. Berthelot, E. D. Raczynska, C. Laurence, Can. J. Chem. 2002, 80, 1375 -1385.
39. R. F. W. Bader, M. T. Carroll, J. R. Cheeseman, C. Chang, J. Am. Chem. Soc. 1987, 109, 7968 -7979.
40. G. Schaftenaar, J. H. Noordik, J. Comput.-Aided Mol. Des. 2000, 14, 123 - 134.
41. E. D. Glendening, A. E. Reed, J. E. Carpenter, F. Weinhold, Natural Bond Orbital (NBO), version 3.1, Theoretical Chemistry Institute, University of Wisconsin, Madison (USA).
42. C. Ouvrard, M. Berthelot, C. Laurence, J. Chem. Soc. Perkin Trans. 2 1999, 1357 -1362.
43. D. A. Deranleau, J. Am. Chem. Soc. 1969, 91, 4044 -4049.
44. M. D. Joesten, R. S. Drago, J. Am. Chem. Soc. 1962, 84, 2037 -2039.
45. C. Ouvrard, M. Berthelot, C. Laurence, J. Phys. Org. Chem. 2001, 14, 804 -810.
46. C. Laurence, M. Berthelot, E. Raczynska, J. Y. Le Questel, G. Duguay, P. Hudhomme, J. Chem. Res. Synop. 1990, 250 - 251.
47. M. Berthelot, M. Helbert, C. Laurence, J. Y. Le Questel, F. Anvia, R. W. Taft, J. Chem. Soc. Perkin Trans. 2 1993, 625 -627.
48. A. Chardin, M. Berthelot, C. Laurence, D. G. Morris, J. Phys. Org. Chem. 1995, 8, 626 - 628.
49. D. G. Lee, R. Srinivasan, Can. J. Chem. 1973, 51, 2542 - 2545.
50. D. P. Stevenson, G. M. Coppinger, J. Am. Chem. Soc. 1962, 84, 149 - 152.
51. W. J. Lautenberger, E. N. Jones, J. G. Miller, J. Am. Chem. Soc. 1968, 90, 1110 -1115.
52. M. Berthelot, C. Laurence, M. Safar, F. Besseau, J. Chem. Soc. Perkin Trans. 2 1998, 283 -290.
53. E. M. Arnett, E. J. Mitchell, T. S. S. R. Murty, J. Am. Chem. Soc. 1974, 96, 3875 -3891.
54. O. Exner, Prog. Phys. Org. Chem. 1973, 10, 411 - 482.
55. L. Liu, Q. X. Guo, Chem. Rev. 2001, 101, 673 -695.
56. R. M. Badger, S. H. Bauer, J. Chem. Phys. 1937, 5, 839 -851.
57. R. M. Badger, J. Chem. Phys. 1940, 8, 288 -289.
58. M. Berthelot, M. Helbert, C. Laurence, J.-Y. Le Questel, J. Phys. Org. Chem. 1993, 6, 302 -306.
59. J. Graton, C. Laurence, M. Berthelot, J.-Y. Le Questel, F. Besseau, E. D. Raczynska, J. Chem. Soc. Perkin Trans. 2 1999, 997 - 1001.
60. M. D. Joesten, R. S. Drago, J. Am. Chem. Soc. 1962, 84, 3817 -3821.
61. R. West, D. L. Powell, M. K. T. Lee, L. S. Whatley, J. Am. Chem. Soc. 1964, 86, 3227 -3229.
62. T. Gramstad, J. Sandstrom, Spectrochim. Acta Part A 1969, 25, 31-38.
63. S. Ghersetti, A. Lusa, Spectrochim. Acta 1965, 21, 1067 - 1071.
64. B. Stymne, H. Stymne, G. Wettermark, J. Am. Chem. Soc. 1973, 95, 3490 - 3494.
65. V. Leunens, P. Migchels, D. Peeters, T. Zeegers-Huyskens, Bull. Soc. Chim. Belg. 1992, 101, 165 - 166.
66. M. C. S. Lopes, H.W. Thompson, Spectrochim. Acta Part A 1968, 24, 1367 - 1383.
67. J. Juffernbruch, H. H. Perkampus, Spectrochim. Acta Part A 1980, 36A, 485 -489.
68. G. C. Pimentel, A. L. McClellan, The Hydrogen Bond, Freeman, San Francisco (USA), 1960.
69. F. Moll, Tetrahedron Lett. 1968, 9, 5201 -5204.
70. F. A. L. Anet, I. Yavari, J. Am. Chem. Soc. 1977, 99, 2794 -2796.
71. S. Scheiner, Hydrogen Bonding: A Theoretical Perspective, Oxford University Press, New York (USA), 1997.
72. F. Weinhold, C. R. Landis, Valency and Bonding: A Natural Bond Orbital Donor-Acceptor Perspective, Cambridge University Press, Cambridge (UK), 2005.
73. P. C. Maria, J. F. Gal, J. De Franceschi, E. Fargin, J. Am. Chem. Soc. 1987, 109, 483 -492.
74. B. Illien, M. Berthelot, D. G. Morris, C. Laurence, J. Phys. Org. Chem. 2000, 13, 293 - 299.
75. A. Chardin, C. Laurence, M. Berthelot, J. Chem. Res. Synop. 1996, 332 - 333.
76. S. C. Blackstock, J. P. Lorand, J. K. Kochi, J. Org. Chem. 1987, 52, 1451 - 1460.
77. J. N. Spencer, E. S. Holmboe, D. W. Firth, M. R. Kirshenbaum, J. Solution Chem. 1981, 10, 745 - 756.
78. C. J. Biaselle, J. G. Miller, J. Am. Chem. Soc. 1974, 96, 3813 -3816.
79. R. Foster, Organic Charge-Transfer Complexes, Academic Press, London (UK), 1969.
80. J. M. Dumas, C. Geron, A. R. Kribii, M. Lakraimi, Can. J. Chem. 1984, 62, 2634 -2640.
81. A. C. Legon, Angew. Chem. 1999, 111, 2850 - 2880;
82. Angew. Chem. Int. Ed. 1999, 38, 2687 - 2714.
83. C. A. Hunter, Angew. Chem. 2004, 116, 5424 -5439;
84. Angew. Chem. Int. Ed. 2004, 43, 5310 - 5324.
85. J. L. Cook, C. A. Hunter, C. M. R. Low, A. Perez-Velasco, J. G. Vinter, Angew. Chem. 2007, 119, 3780 -3783;
86. Angew. Chem. Int. Ed. 2007, 46, 3706 -3709.
87. G. Guiheneuf, K. Sraidi, R. Claramunt, J. Elguero, C. R. Acad. Sci. Ser. II 1987, 305, 567 -569.
88. M. H. Abraham, P. P. Duce, D. V. Prior, D. G. Barratt, J. J. Morris, P. J. Taylor, J. Chem. Soc. Perkin Trans. 2 1989, 1355 - 1375.
89. C. Hansch, A. Leo, R. W. Taft, Chem. Rev. 1991, 91, 165 -195.