Uncommon aqueous media for nitrilimine cycloadditions. II. Computational study of the effect of water on reaction rate

New Journal of Chemistry

Volumn 26, Issue 10, 2002, Pages 1346-1351

  Ponti, Alessandro ^a   Molteni, Giorgio ^a  

^a CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; IMINE; NITRILIMINE; UNCLASSIFIED DRUG; WATER;

AB INITIO CALCULATION; AQUEOUS SOLUTION; ARTICLE; CALCULATION; CATALYSIS; CATALYST; CHEMICAL REACTION; CYCLOADDITION; HYDROGEN BOND; POLARIZATION; PRIORITY JOURNAL; REACTION TIME;

EID: 0036402544     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: 10.1039/b205071d     Document Type: Article

References (41)

1. (a) Giorgio Molteni, Alessandro Ponti and Marco Orlandi, New J. Chem., 2002, 26, (DOI: 10.1039/b205063c);
2. (b) P. Caramella and P. Grünanger, in 1,3-Dipolar Cycloaddition Chemistry, ed. A. Padwa, Wiley-Interscience, New York, USA, 1984, vol. 1, ch. 3;
3. (c) G. Broggini, G. Molteni and G. Zecchi, Heterocycles, 1998, 47, 541.
4. H. Zollinger, Color Chemistry, VCH Press, Weinheim, Germany, 1988.
5. G. Molteni, M. Orlandi and G. Broggini, J. Chem. Soc., Perkin Trans. 1, 2000, 3742.
6. T. Shimizu, Y. Hayashi, T. Nishio and K. Teramura, Bull. Chem. Soc. Jpn., 1984, 57, 787.
7. K. Fukui, Science, 1982, 218, 747.
8. (a) R. G. Pearson, J. Am. Chem. Soc., 1963, 85, 3533;
9. (b) P. K. Chattaraj, H. Lee and R. G. Parr, J. Am. Chem. Soc., 1991, 113, 1855.
10. H. Chermette, J. Comput. Chem., 1999, 20, 129.
11. R. G. Parr and W. Yang, Density Functional Theory of Atoms and Molecules, Oxford University Press, Oxford, UK, 1989.
12. (a) A. K. Chandra and M. T. Nguyen, J. Comput. Chem., 1998, 19, 195;
13. (b) A. K. Chandra and M. T. Nguyen, J. Phys. Chem. A, 1998, 102, 6181;
14. (c) F. Méndez, J. Tamariz and P. Geerlings, J. Phys. Chem. A, 1998, 102, 6292;
15. (d) T. N. Le, L. T. Nguyen, A. K. Chandra, F. De Proft, P. Geerlings and M. T. Nguyen, J. Chem. Soc., Perkin Trans. 2, 1999, 1249;
16. (e) A. K. Chandra, T. Uchimaru and M. T. Nguyen, J. Chem. Soc., Perkin Trans. 2, 1999, 2117;
17. (f) P. Geerlings and F. De Proft, Int. J. Quantum Chem., 2000, 80, 227;
18. (g) L. Domingo, Eur. J. Org. Chem., 2000, 2265;
19. (h) R. Herrera, A. Nagarajan, M. A. Morales, F. Méndez, H. A. Jiménez-Vázquez, L. G. Zepeda and J. Tamariz, J. Org. Chem., 2001, 66, 1252;
20. (i) L. T. Nguyen, F. De Proft, A. K. Chandra, T. Uchimaru, M. T. Nguyen and P. Geerlings, J. Org. Chem., 2001, 66, 6096.
21. A. Ponti, J. Phys. Chem. A, 2000, 104, 8843.
22. K. N. Houk, J. Sims, C. R. Watts and L. J. Luskus, J. Am. Chem. Soc., 1973, 95, 7301.
23. J. Tomasi and M. Persico, Chem. Rev., 1994, 94, 2027.
24. (a) A. Rastelli, R. Gandolfi and M. Sarzi Amadè, J. Org. Chem., 1998, 63, 7425;
25. (b) F. P. Cossío, I. Morao, H. Jiao and P. v. R. Schleyer, J. Am. Chem. Soc., 1999, 121, 6737;
26. (c) L. Domingo, Eur. J. Org. Chem., 2000, 2265;
27. (d) Y. Hu and K. N. Houk, Tetrahedron, 2000, 56, 8239;
28. (e) L. T. Nguyen, F. De Proft, A. K. Chandra, T. Uchimaru, M. T. Nguyen and P. Geerlings, J. Org. Chem., 2001, 66, 6096.
29. A. D. Becke, J. Chem. Phys., 1993, 98, 5648.
30. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle and J. A. Pople, Gaussian 98, Revision A.7, Gaussian, Inc., Pittsburgh PA, USA, 1998.
31. W. Yang and W. J. Mortier, J. Am. Chem. Soc., 1986, 108, 5708.
32. R. G. Parr and W. Yang, J. Am. Chem. Soc., 1984, 106, 4049.
33. (a) U. C. Singh and P. A. Kollman, J. Comput. Chem., 1984, 5, 129;
34. (b) B. H. Besler, K. M. Merz, Jr. and P. A. Kollman, J. Comput. Chem., 1990, 11, 431.
35. F. De Proft, J. M. L. Martin and P. Geerlings, Chem. Phys. Lett., 1996, 250, 393.
36. P. K. Chattaraj, J. Phys. Chem., 2001, 105, 511.
37. (a) R. Sustmann, Tetrahedron Lett., 1971, 2717;
38. (b) R. Sustmann and H. Trill, Angew. Chem., Int. Ed. Engl., 1972, 11, 838.
39. J. L. Gázquez and F. Méndez, J. Phys. Chem., 1994, 98, 4591.
40. S. Damoun, G. van de Woude, F. Méndez and P. Geerlings, J. Phys. Chem. A, 1997, 101, 886.
41. A. Ponti and G. Molteni, J. Org. Chem., 2001, 66, 5252.