An ab initio study of the trimethylamine-formic acid and the trimethylammonium ion-formate anion complexes, their monohydrates, and continuum solvation

Journal of the American Chemical Society

Volumn 119, Issue 5, 1997, Pages 1052-1058

  Liljefors, Tommy ^a   Norrby, Per Ola ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

QUATERNARY AMMONIUM DERIVATIVE;

ARTICLE; COMPLEX FORMATION; IN VITRO STUDY; REACTION ANALYSIS; THEORY; THERMODYNAMICS;

EID: 84962434220     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9616692     Document Type: Article

References (40)

1. Fersht, A. R. Enzyme structure and mechanism; W. H. Freeman and Company: New York. 1985.
2. Tomic, M.; Seeman, P.; George, S. R.; O'Dowd, B. F. Biochem. Biophys. Res. Commun. 1993, 191, 1020.
3. Mansour, A.; Meng, F.; Meador-Woodruff, J. H.; Taylor, L. P.; Civelli O.; Akil, H. Eur. J. Pharmacol. 1992, 227, 205.
4. Hibert, M.; Trumpp-Kallmeyer, S.; Bruinvels, A.; Hoflack, J. Mol. Pharmacol. 1991, 40, 8.
5. Trumpp-Kallmeyer, S.; Hoflack, J.; Bruinvels, A.; Hibert, M. J. Med. Chem. 1992, 35, 3448.
6. Moreels, M.; Leysen, J. E. Recept. Channels 1993, 1, 89.
7. Teeter, M. M.; Froimowitz, M.; Stec, B.; DuRand, C. J. J. Med. Chem. 1994, 37, 2874.
8. Hutchins, C. Endocr. J. 1994, 2, 7.
9. Heidrich, D.; van Eikema Hommes, N. J. R.; von Ragué Schleyer, P. J. Comput. Chem. 1993, 14, 1149.
10. Sapse, A. M.; Russell, C. S. J. Mol. Struct. (Theochem) 1986, 137, 43.
11. Zheng, Y.-J.; Mertz, K. M., Jr. J. Comput. Chem. 1992, 13, 1151.
12. Ding, Y.; Krogh-Jespersen, K. Chem. Phys. Lett. 1992, 119, 261.
13. Ding, Y.; Krogh-Jespersen, K. J. Comput. Chem. 1996, 17, 338.
14. Jensen, J. H.; Gordon, M. S. J. Am. Chem. Soc. 1995, 117, 8159.
15. (a) Horn, A. S. Dopamine Receptors. In Comprehensive Medicinal Chemistry; Hansch, C., Sammes, P. G., Taylor, J. B., Eds.; Pergamon Press: Oxford, 1990; Vol. 3, pp 229-290.
16. (b) Hibert, M. F.; Mir, A. K.; Fozard, J. R. Serotonin (5-HT) Receptors. In Comprehensive Medicinal Chemistry; Hansch, C., Sammes, P. G., Taylor, J. B., Eds.; Pergamon Press: Oxford, 1990; Vol. 3, pp 567-600.
17. (a) Chang, Y.-A.; Ares, J.; Anderson, K.; Sabol, B.; Wallace, R. A.; Farooqui, T.; Uretsky, N.; Miller, D. D. J. Med. Chem. 1987, 30, 214.
18. (b) Harrold, M. W.; Chang, Y.-A.; Wallace, R. A.; Farooqui, T.; Wallace, L. J.; Miller, D. D. J. Med. Chem. 1987, 30, 1631.
19. (c) Wallace, R. A.; Farooqui, T.; Wallace, L.; Ares, J.; Chang, Y.-A.; Miller, D.; Uretsky, N. Biochem. Pharmacol. 1987, 36, 3903.
20. (d) Tsai, R.-S.; Carrupt, P.-A.; Testa, B.; Gaillard, P.; El Tayar, N. J. Med. Chem. 1993, 36, 196.
21. (e) Harrold, M. W.; Sriburi, A.; Matsumoto, K.; Miller, D. D.; Farooqui, T.; Uretsky, N. J. Med. Chem. 1993, 36, 3166.
22. (f) Liljefors, T.; Norrby, P.-O. In Structure and Functions of 7TM Receptors; Schwartz, T. W., Hjort, S. A., Sandholm Kastrup, J., Eds.; Munksgaard: Copenhagen, 1996; pp 194-204.
23. Munson, M. S. B. J. Am. Chem. Soc. 1965, 87, 2332.
24. Gaussian 92, Revision F.3, Frisch, M. J.; Trucks, G. W.; Head-Gordon, M.; Gill, P. M. W.; Wong, M. W.; Foresman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M. A.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A.; Gaussian, Inc.: Pittsburgh, PA, 1992.
25. Gaussian 94, Revisions B.3 and D.1, Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A.; Gaussian, Inc.: Pittsburgh, PA, 1995.
26. Spartan SGI version 4.0.3, GL Wavefunction Inc.: 18401 von Karman, suite 370, Irvine, CA 92715.
27. Cramer, C. J.; Truhlar, D. J. J. Comput.-Aided Mol. Des. 1992, 6, 629.
28. The SCI-PCM method has not yet been published (Douglas J. Fox, personal communication). For a brief description, see the Gaussian 94 manual and Foresman, J. B.; Frisch, A. Exploring Chemistry with Electronic Structure Methods, 2nd ed.; Gaussian, Inc.: Pittsburgh, PA, 1995-96; pp 237-249. For a description of the underlying PCM and IPCM methods, see: (a) Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, 117. (b) Foresman, J. B.; Keith, T. A.; Wiberg, K. B.; Snoonlan, J.; Frisch, M. J. J. Phys. Chem. 1996, 100, 16098.
29. The SCI-PCM method has not yet been published (Douglas J. Fox, personal communication). For a brief description, see the Gaussian 94 manual and Foresman, J. B.; Frisch, A. Exploring Chemistry with Electronic Structure Methods, 2nd ed.; Gaussian, Inc.: Pittsburgh, PA, 1995-96; pp 237-249. For a description of the underlying PCM and IPCM methods, see: (a) Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, 117. (b) Foresman, J. B.; Keith, T. A.; Wiberg, K. B.; Snoonlan, J.; Frisch, M. J. J. Phys. Chem. 1996, 100, 16098.
30. The SCI-PCM method has not yet been published (Douglas J. Fox, personal communication). For a brief description, see the Gaussian 94 manual and Foresman, J. B.; Frisch, A. Exploring Chemistry with Electronic Structure Methods, 2nd ed.; Gaussian, Inc.: Pittsburgh, PA, 1995-96; pp 237-249. For a description of the underlying PCM and IPCM methods, see: (a) Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, 117. (b) Foresman, J. B.; Keith, T. A.; Wiberg, K. B.; Snoonlan, J.; Frisch, M. J. J. Phys. Chem. 1996, 100, 16098.
31. The SCI-PCM method has not yet been published (Douglas J. Fox, personal communication). For a brief description, see the Gaussian 94 manual and Foresman, J. B.; Frisch, A. Exploring Chemistry with Electronic Structure Methods, 2nd ed.; Gaussian, Inc.: Pittsburgh, PA, 1995-96; pp 237-249. For a description of the underlying PCM and IPCM methods, see: (a) Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, 117. (b) Foresman, J. B.; Keith, T. A.; Wiberg, K. B.; Snoonlan, J.; Frisch, M. J. J. Phys. Chem. 1996, 100, 16098.
32. Allen, F. H.; Bellard, S.; Brice, M. D.; Cartwright, B. A.; Doubleday, A.; Higgs, H.; Hummelink, T.; Hummelink-Peters, B. G.; Kennard, O.; Motherwell, W. D. S.; Rogers, J. R.; Watson, D. G. Acta Crystallogr. 1979, B35, 2331.
33. Protein Data Bank, Chemistry Department, Building 555, Brookhaven National Laboratory, Upton, NY 11973.
34. (a) Oh, B.-H.; Pandit, J.; Kang, C.-H.; Nikaido, K.; Gokcen, S.; Ames, G. F.-L.; Kim, S.-H. J. Biol. Chem. 1993, 268, 11348.
35. (b) Brookhaven Protein Data Bank entry 1LST.
36. (a) Kurinov, I.; Harrison, R. W. Nature Struct. Biol. 1994, 1, 735.
37. (b) Kurinov, I.; Harrison, R. W.; Brookhaven Protein Data Bank entries 1TNG, 1TNH, 1TNI, 1TNJ, 1TNK, 1TNL for complexes between trypsin and 2-aminocyclohexane, 4-fluorobenzylamine, 4-phenylbutylamine, 2-phenylethylamine, 3-phenylpropylamine, and tranylcypromine, respectively.
38. Denisov, G. S.; Golubev, N. S. J. Mol. Struct. 1981, 75, 311.
39. Aue, D. H.; Bowers, M. T. In Gas Phase Ion Chemistry; Bowers, M. T., Ed.; Academic Press: New York, 1979; Vol. 2, pp 1-51.
40. Bartmess, J. E.; McIver, R. T., Jr., In Gas Phase Ion Chemistry; Bowers, M. T.; Ed.; Academic Press: New York, 1979; Vol. 2, pp 88-121.