Quantum mechanical conformational analysis of β-alanine zwitterion in aqueous solution

Journal of the American Chemical Society

Volumn 122, Issue 13, 2000, Pages 3151-3155

  Nielsen, Peter Aadal ^a   Norrby, Per Ola ^a   Liljefors, Tommy ^a   Rega, Nadia ^b   Barone, Vincenzo ^b  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHOLYTE; BETA ALANINE; SOLVENT;

AQUEOUS SOLUTION; ARTICLE; CONFORMATION; HYDROGEN BOND; MOLECULAR INTERACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLARIZATION; QUANTUM MECHANICS; SOLVATION;

EID: 0034607389     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992902+     Document Type: Article

References (35)

1. Pettersson, I.; Liljefors, T. J. Comput. Aided Mol. Design 1987, 1, 143.
2. Bengtsson, M.; Liljefors, T.; Hansson, B. S. Bioorg. Chem. 1987, 15, 409.
3. (a) Rivail, J. L.; Rinaldi, D.; Ruiz-Lopez, F. Liquid-State Quantum Chemistry. In Computational Chemistry: Review of Current Trends; Lesczynski, J., Ed.; World Scientific: Singapore, 1995; p 195.
4. (b) Cramer, C. J.; Truhlar, D. J. In Reviews in Computational Chemistry, Lipkowitz, K. B., Boyd, B., Eds.; VCH Publishers: New York, 1995; Vol. 6, p 1.
5. (c) Amovilli, C.; Barone, V.; Cammi, R.; Cances, E.; Cossi, M.; Mennucci, B.; Pomelli, C. S.; Tomasi, J. Adv. Quantum Chem. 1999, 32, 227.
6. (a) Orozco, M.; Alhambra, C.; Barril, X.; Lopez, J. M.; Busquets, M.; Luque, F. J. Mol. Model. 1996, 2, 1.
7. (b) Rega, N.; Cossi, M.; Barone, V.; Pomelli, C. S.; Tomasi, J. Int. J. Quantum Chem. 1999, 73, 219.
8. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipron, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440.
9. Bostrom, J.; Norrby, P.-O.; Liljefors, T. J. Comput. Aided Mol. Design 1998, 12, 383.
10. Liljefors, T.; Norrby, P.-O. J. Am. Chem. Soc. 1997, 119, 1052.
11. Norrby, P.-O.; Liljefors, T. J. Am. Chem. Soc. 1999, 121, 2303.
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. Rega, N.; Cossi, M.; Barone, V. J. Am. Chem. Soc. 1998, 120, 5723.
16. Barone, V.; Bencini, A.; Cossi, M.; di Matteo, A.; Mattesini, M.; Totti, F. J. Am. Chem. Soc. 1998, 120, 7069.
17. Adamo, C.; di Matteo, A.; Rey, P.; Barone, V. J. Phys. Chem. A 1999, 103, 3481.
18. Gregoire, F.; Wei, S. H.; Streed, E. W.; Brameld, K. A.; Fort, D.; Hanely, L. J.; Goddard, W. A.; Roberts, J. D. J. Am. Chem. Soc. 1998, 120, 7537.
19. Abraham, R. J.; Loftus, P.; Thomas, A. W. Tetrahedron 1977, 33, 1227.
20. Karplus, M. J. Chem. Phys. 1959, 30, 11.
21. Karplus, M. J. Am. Chem. Soc. 1963, 85, 2870.
22. Ford, P. F.; Wang, P. J. Am. Chem. Soc. 1992, 114, 10563.
23. Gresh, N.; Pullmann, A.; Claverie, P. Theor. Chim. Acta 1985, 67, 11.
24. Jaguar release 16 software package from Schrodinger, Inc.
25. Gaussian 98, (Revision A.7), Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; 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.; Mennucci, 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.; Stefanov, B. B.; Lin, 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.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian, Inc.: Pittsburgh, PA, 1999.
26. Description of basis sets and explanation of standard levels of theory can be found in the following: Foresman, J. B.; Frisch, AE. Exploring Chemistry with Electronic Structure Methods. 2nd ed.; Gaussian Inc.: Pittsburgh, PA, 1996.
27. Cossi, M.; Barone, V.; Cammi, R.; Tomasi, J. Chem. Phys. Lett. 1996, 255, 327.
28. Barone, V.; Cossi, M.; Tomasi, J. J. Comput. Chem. 1998, 19, 404.
29. Cossi, M.; Barone, V. J. Chem. Phys. 1998, 109, 6246.
30. Barone, V.; Cossi, M.; Tomasi, J. J. Chem. Phys. 1997, 107, 3210.
31. Barone, V.; Cossi M. J. Phys. Chem. A 1998, 102, 1995.
32. Klamt, A.; Schüürmann, J. Chem. Soc., Perkins Trans. 1993, 2, 799.
33. Minichino, C.; Barone, V. J. Chem. Phys. 1994, 100, 3717.
34. Barone, V.; Minichino, C. Theochem 1995, 330, 325.
35. Altona, C.; Francke, R.; de Haan, R.; Ippel, J. H.; Daalmans, G. J.; Westra Hoekzema, A. J. A.; van Wijk, S. Magn. Reson. Chem. 1994, 32, 670.