Conformational preferences of 2-phenethylamines. A computational study of substituent and solvent effects on the intramolecular amine-aryl interactions in charged and neutral 2-phenethylamines

Journal of the American Chemical Society

Volumn 119, Issue 50, 1997, Pages 12292-12299

  Urban, Joseph J ^a   Cronin, Curtis W ^a   Roberts, Ralph R ^b,d   Famini, George R ^c  

^a UNITED STATES NAVAL ACADEMY   (United States)

^b HOWARD UNIVERSITY   (United States)

^c International Programs Office   (United States)

^d 3M COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHENETHYLAMINE; SOLVENT;

AQUEOUS SOLUTION; ARTICLE; CALCULATION; CONFORMATION; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; SOLVATION; TECHNIQUE;

EID: 0031576673     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja971866g     Document Type: Article

References (39)

1. Urban, J. J.; Cramer, C. J.; Famini, G., R. J. Am. Chem. Soc. 1992, 114, 8226.
2. Solmajer, P.; Kocjan, D.; Solmajer, T. Z. Naturforsch. 1983, 38c, 758.
3. Kearney, P. C.; Mizoue, L. S.; Kumpf, R. A.; Forman, J. E.; McCurdy, A.; Dougherty, D. A. J. Am. Chem. Soc. 1993, 115, 9907.
4. Dougherty, D. A.; Stauffer, D. A. Science 1990, 250, 1558.
5. Sussman, J. L.; Harel, M.; Frolow, F.; Oefner, C.; Goldman, A.; Toker, L.; Silman, I. Science 1991, 255, 872-879.
6. Martinez, S. J., III; Alfano, J. C.; Levy, D. H. J. Mol. Spectrosc. 1993, 158, 82-92.
7. Martin, M.; Carbo, R.; Petroneglo, C.; Tomasi, J. J. Am. Chem. Soc. 1975, 97, 1338.
8. Pullman, B.; Berthold, H.; Courriere, P. Int. J. Quantum Chem. 1974, 1, 93.
9. Pullman, B.; Coubeils, J.-L.; Courriere, P.; Gervois, J.-P. J. Med. Chem. 1972, 15, 17.
10. Choi, Y.; Lubman, D. M. Anal. Chem. 1992, 64, 2726.
11. Godfrey, P. D.; Hatherley, L. D.; Brown, R. D. J. Am. Chem. Soc. 1995, 117, 8204-8210.
12. Sun, S.; Bernstein, E. R. J. Am. Chem. Soc. 1996, 118, 5086-5095.
13. Still, W. C.; Tempczyk, A.; Hawley, R. C.; Hendrickson, T. J. Am. Chem. Soc. 1990, 112, 6127-6129.
14. Cramer, C. J.; Truhlar, D. G. J. Comput.-Aid. Mol. Des. 1992, 6, 629-666.
15. 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.; Repogle, E. S.; Comparts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Steward, J. J. P.; Pople, J. A. Gaussian, Inc.: Pittsburgh, PA, 1992.
16. Frisch, M. J.; Trucks, G. W.; Schlege, 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. Gaussian94, Revision E.2 1994.
17. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
18. Liotard, D. L.; Healy, E. F.; Ruiz, J. M.; Dewar, M. J. S. QCPE Bull 1989, 9, 123.
19. Cramer, C. J.; Truhlar, D. G. QCPE Bull. 1991, 11, 57.
20. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440.
21. Storer, J. W.; Giesen, D. J.; Cramer, C. J.; Truhlar, D. G. J. Comput.-Aid. Mol. Des. 1995, 9, 87-110.
22. Urban, J. J.; Famini, G., R. J. Comput. Chem. 1992, 14, 353-362.
23. Orville-Thomas, W. J. Internal Rotation in Molecules; Orville-Thomas, W. J., Ed.; John Wiley and Sons: London, 1974.
24. Breen, P. J.; Warren, J. A.; Bernstein, E. R.; Seeman, J. I. J. Chem. Phys. 1987, 87, 1927.
25. Hopkins, J. B.; Powers, D. E.; Smalley, R. E. J. Chem. Phys. 1980, 72, 5039.
26. Hopkins, J. B.; Powers, D. E.; Mukamel, S.; Smalley, R. E. J. Am. Chem. Soc. 1980, 72, 5049.
27. Nishio, M.; Hirota, M. Tetrahedron 1989, 45, 72001-7245.
28. Sakakibara, K.; Allinger, N. L. J. Org. Chem. 1995, 60, 4044-4050.
29. Nagy, P. I.; Durant, G. J.; Hoss, W. P.; Smith, D. A. J. Am. Chem. Soc. 1994, 116, 4898-4909.
30. Cook, M. J.; Tauqeer, A. H.; Khalida, N. Tetrahedron 1986, 42, 249.
31. Grunewald, G. L.; Creese, M. W.; Weintraub, H. J. R. J. Comput. Chem. 1988, 9, 315-326.
32. Williams, D. E. Biopolymers 1990, 29, 1367-1386.
33. Stouch, T. R.; Williams, D. E. J. Comput. Chem. 1992, 13, 622-632.
34. Cornell, W. D.; Cieplak, P.; Bayly, C. I.; Kollman, P. A. J. Am. Chem. Soc. 1993, 115, 9620-9631.
35. Reynolds, C. A.; Essex, J. W.; Richards, W. G. J. Am. Chem. Soc. 1992, 114, 9075.
36. Cramer, C. J.; Truhlar, D. G. J. Am. Chem. Soc. 1991, 113, 8305.
37. Cramer, C. J.; Truhlar, D. G. Continuum Solvation Models: Classical and Quantum Mechanical Implementations. In Reviews in Computational Chemistry; Lipkowitz, K. B., Boyd, D. B., Eds.; VCH: New York, 1995; Vol. 6.
38. Makriyannis, A.; Knittel, J. Tetrahedron Lett. 1981, 22, 4631-4634.
39. Martin, I. L.; Baker, G. B.; Hamor, T. A.; Jennings, W. B.; Paxton, K. Acta Crystallogr. 1978, B34, 2176-2180.