An enthalpic scale of hydrogen-bond basicity. 3. Ammonia, primary, secondary, and tertiary amines

Journal of Organic Chemistry

Volumn 70, Issue 20, 2005, Pages 7892-7901

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

^a UNIVERSITÉ DE NANTES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALINITY; AMINES; ELECTRIC FIELDS; ENTHALPY; ENTROPY; PHENOLS;

ALIPHATIC AMINES; ELECTRONIC ENERGY; ENTHALPY-ENTROPY RELATIONSHIP; HYDROGEN-BOND ACCEPTOR STRENGTH;

HYDROGEN BONDS;

ALIPHATIC AMINE; ALKYL GROUP; AMINE; AMMONIA; CARBON TETRACHLORIDE; LEWIS BASE; PHENOL DERIVATIVE; TERTIARY AMINE;

ARTICLE; ELECTRICITY; ENERGY; ENTHALPY; ENTROPY; HYDROGEN BOND; INFRARED SPECTROSCOPY; STEREOCHEMISTRY; TEMPERATURE;

EID: 25444505975     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050535g     Document Type: Article

References (81)

1. Pimentel, G. C.; McClellan, A. L. The Hydrogen Bond; Freeman: San Francisco, 1960.
2. Jeffrey, G. A.; Saenger, W. Hydrogen Bonding in Biological Structures; Springer-Verlag: Berlin, 1991.
3. Scheiner, S. Hydrogen Bonding: A Theoretical Perspective; Oxford University Press: New York, 1997.
4. Liu, L.; Guo, Q. X. Chem. Rev. 2001, 101, 673-695.
5. Arnett, E. M.; Mitchell, E. J.; Murty, T. S. S. R. J. Am. Chem. Soc. 1974, 96, 3875-3891.
6. Badger, R. M.; Bauer, S. H. J. Chem. Phys. 1937, 5, 839-851.
7. Badger, R. M. J. Chem. Phys. 1940, 8, 288-289.
8. Joesten, M. D.; Drago, R. S. J. Am. Chem. Soc. 1962, 84, 3817-3821.
9. Gramstad, T. Spectrochim. Acta 1963, 19, 497-508.
10. Neerinck, D.; Lamberts, L. Bull. Soc. Chim. Belg. 1966, 75, 473-483.
11. Neerinck, D.; Lamberts, L. Bull. Soc. Chim. Belg. 1966, 75, 484-497.
12. Barakat, T. M.; Nelson, M. J.; Nelson, S. M.; Pullin, A. D. E. Trans. Faraday Soc. 1966, 62, 2674-2684.
13. Epley, T. D.; Drago, R. S. J. Am. Chem. Soc. 1967, 89, 5770-5773.
14. Purcell, K. F.; Stikeleather, J. A.; Brunk, S. D. J. Am. Chem. Soc. 1969, 91, 4019-4027.
15. Drago, R. S.; Epley, T. D. J. Am. Chem. Soc. 1969, 91, 2883-2890.
16. Vogel, G. C.; Drago, R. S. J. Am. Chem. Soc. 1970, 92, 5347-5351.
17. Drago, R. S.; O'Bryan, N.; Vogel, G. C. J. Am. Chem. Soc. 1970, 92, 3924-3929.
18. Sherry, A. D.; Purcell, K. F. J. Am. Chem. Soc. 1972, 94, 1853-1857.
19. West, R.; Powell, D. L.; Whatley, L. S.; Lee, M. K. T.; Schleyer, P. v. R. J. Am. Chem. Soc. 1962, 84, 3221-3222.
20. Arnett, E. M.; Joris, L.; Mitchell, E.; Murty, T. S. S. R.; Gorrie, T. M.; Schleyer, P. v. R. J. Am. Chem. Soc. 1970, 92, 2365-2377.
21. Becker, E. D. Spectrochim. Acta 1961, 17, 436-447.
22. Powell, D. L.; West, R. Spectrochim. Acta 1964, 20, 983-991.
23. Singh, S.; Murthy, A. S. N.; Rao, C. N. R. Trans. Faraday Soc. 1966, 62, 1056-1066.
24. Gramstad, T.; Sandstrom, J. Spectrochim. Acta, Part A 1969, 25, 31-38.
25. Rossarie, J.; Gallas, J. P.; Binet, C.; Romanet, R. J. Chim. Phys. Phys.-Chim. Biol. 1978, 75, 63-73.
26. Goralski, P. J. Chem. Soc., Faraday Trans. 1993, 89, 2433-2435.
27. Abraham, M. H.; Prior, D. V.; Schulz, R. A.; Morris, J. J.; Taylor, P. J. J. Chem. Soc., Faraday Trans. 1998, 94, 879-885.
28. Jensen, W. B. The Lewis Acid-Base Concepts: An Overview; Wiley: New York, 1980.
29. Gutmann, V. Electrochim. Acta 1976, 21, 661-670.
30. Drago, R. S. Coord. Chem. Rev. 1980, 33, 251-277.
31. Maria, P. C.; Gal, J. F. J. Phys. Chem. 1985, 89, 1296-1304.
32. Gurka, D.; Taft, R. W. J. Am. Chem. Soc. 1969, 91, 4794-4801.
33. Taft, R. W.; Gurka, D.; Joris, L.; Schleyer, P. v. R.; Rakshys, J. W. J. Am. Chem. Soc. 1969, 91, 4801-4808.
34. Abraham, M. H.; Duce, P. P.; Prior, D. V.; Barratt, D. G.; Morris, J. J.; Taylor, P. J. J. Chem. Soc., Perkin Trans. 2 1989, 1355-1375.
35. Abraham, M. H.; Grellier, P. L.; Prior, D. V.; Morris, J. J.; Taylor, P. J. J. Chem. Soc., Perkin Trans. 2 1990, 521-529.
36. Ouvrard, C.; Berthelot, M.; Laurence, C. J. Phys. Org. Chem. 2001, 14, 804-810.
37. Laurence, C.; Berthelot, M.; Evain, K.; Illien, B. Can. J. Chem. 2005, 83, 138-145.
38. Gramstad, T. Acta Chem. Scand. 1962, 16, 807-819.
39. Lamberts, L.; Zeegers-Huyskens, T. J. Chim. Phys. Phys.-Chim. Biol. 1963, 60, 435-441.
40. Horak, M.; Sara, V.; Moravec, J. Collect. Czech. Chem. Commun. 1972, 37, 1990-1992.
41. Shah, S. B.; Murthy, A. S. N. Ind. J. Chem. 1976, 14A, 100-103.
42. Shah, S. B.; Murthy, A. S. N. Ind. J. Chem. 1976, 14A, 104-106.
43. Libus, W.; Mecik, M.; Sulek, W. J. Solution Chem. 1977, 6, 865-879.
44. Kogowski, G.; Scott, R. M.; Filisko, F. J. Phys. Chem. 1980, 84, 2262-2265.
45. Spencer, J. N.; Wolbach, W. S.; Hovick, J. W.; Ansei, L.; Modarress, K. J. J. Solution Chem. 1985, 14, 805-814.
46. Dwivedi, P. C.; Banga, A. K.; Sharma, N. Spectrochim. Acta, Pari A 1986, 42A, 623-629.
47. Orban, M.; Kiss, A.; Barcza, L. J. Chem. Soc., Perkin Trans. 2 1987, 1815-1817.
48. Wiberg, K. B. In Physical Organic Chemistry; Wiley: New York, 1964; p 378.
49. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry; Wiley-VCH: Weiheim, 2003.
50. Stevenson, D. P.; Coppinger, G. M. J. Am. Chem. Soc. 1962, 84, 149-152.
51. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A. J.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Menucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; 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.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.9; Gaussian, Inc.: Pittsburgh, PA, 1998.
52. Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553-566.
53. Xantheas, S. S. J. Chem. Phys. 1996, 104, 8821-8824.
54. Rablen, P. R.; Lockman, J. W.; Jorgensen, W. L. J. Phys. Chem. A 1998, 102, 3782-3797.
55. Exner, O. Prog. Phys. Org. Chem. 1973, 10, 411-82.
56. IKR program; http://www.sciences.univ-nantes.fr/spectro/publicat.htm#P17.
57. Ouvrard, C.; Berthelot, M.; Lamer, T.; Exner, O. J. Chem. Inf. Comput. Sci. 2001, 41, 1141-1144.
58. Graton, J.; Berthelot, M.; Gal, J. F.; Laurence, C.; Lebreton, J.; Le Questel, J. Y.; Maria, P. C.; Robins, R. J. Org. Chem. 2003, 68, 8208-8221.
59. Joesten, M. D.; Drago, R. S. J. Am. Chem. Soc. 1962, 84, 2037-2039.
60. Graton, J.; Besseau, F.; Berthelot, M.; Raczynska, E. D.; Laurence, C. Can. J. Chem. 2002, 80, 1375-1385.
61. Graton, J.; Laurence, C.; Berthelot, M.; Le Questel, J.-Y.; Besseau, F.; Raczynska, E. D. J. Chem. Soc., Perkin Trans. 2 1999, 997-1001.
62. Graton, J.; Berthelot, M.; Laurence, C. J. Chem. Soc., Perkin Trans. 2 2001, 2130-2135.
63. Graton, J. Ph.D. Thesis, University of Nantes, 2001.
64. Hepler, L. G. Thermochim. Acta 1981, 50, 69-72.
65. -1: Hirano, E.; Kojima, K. Bull. Chem. Soc. Jpn. 1966, 39, 1216-1220). Thus, a CPU time of ca. 6 days is required to reach a chemically significant result in vacuo for a small complex (12 heavy atoms). Therefore, a reliable absolute calculation on a significant sample of larger and more flexible amines in the presence of solvent seems unlikely to be achieved today in our laboratory. Consequently, we have turned to the calculation of a simple quantum-mechanical descriptor of enthalpy (vide infra).
66. Lamarche, O.; Platts, J. A. Chem. Eur. J. 2002, 8, 457-466.
67. Le Questel, J.-Y.; Berthelot, M.; Laurence, C. J. Phys. Org. Chem. 2000, 13, 347-358.
68. Marco, J.; Orza, J. M.; Notario, R.; Abboud, J.-L. M. J. Am. Chem. Soc. 1994, 116, 8841-8842.
69. Hunter, E. P. L.; Lias, S. G. J. Phys. Chem. Ref. Data 1998, 27, 413-656.
70. Perrin, D. D. Dissociation Constants of Organic Bases in Aqueous Solution. (Pure and Applied Chemistry); Butterworth: London, 1965.
71. Murrell, J. N.; Kettle, S. F. A.; Tedder, J. M. The Chemical Bond; Wiley: New York, 1978.
72. Ouvrard, C.; Le Questel, J. Y.; Berthelot, M.; Laurence, C. Acta Crystallogr., Sect. B 2003, 59, 512-526.
73. Maria, P. C.; Gal, J. F.; De Franceschi, J.; Fargin, E. J. Am. Chem. Soc. 1987, 109, 483-492.
74. Kamlet, M. J.; Gal, J. F.; Maria, P. C.; Taft, R. W. J. Chem. Soc., Perkin Trans. 2 1985, 1583-1589.
75. Mulliken, R. S.; Person, W. B. Molecular Complexes; Wiley: New York, 1969.
76. Klopman, G. J. Am. Chem. Soc. 1968, 90, 223-234.
77. Pearson, R. G. J. Am. Chem. Soc. 1985, 107, 6801-6806.
78. Laurence, C.; Queignec-Cabanetos, M.; Dziembowska, T.; Queignec, R.; Wojtkowiak, B. J. Am. Chem. Soc. 1981, 103, 2567-2573.
79. Alkorta, I.; Rozas, I.; Elguero, J. J. Phys. Chem. A 1998, 102, 9278-9285.
80. El Ghomari, M. J. Ph.D. Thesis, University of Nantes, 1996.
81. Roberts, J. D.; Caserio, M. C. Basic Principles of Organic Chemistry; W. A. Benjamin, Inc.: New York, 1964; Chapter 19.