Differential behavior of amino-imino constitutional isomers in nonlinear optical processes

ChemPhysChem

Volumn 11, Issue 4, 2010, Pages 912-919

  Latorre, Sonia ^a   de Moreira, Ibério P R ^b   Villacampa, Belén ^c   Julià, Lluís ^d   Velasco, Dolores ^a   Bofill, Josep Maria ^b   López Calahorra, Francisco ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b UNIVERSITY OF BARCELONA   (Spain)

^c UNIVERSITY OF ZARAGOZA   (Spain)

^d INSTITUTE OF ADVANCED CHEMISTRY OF CATALONIA IQAC CSIC   (Spain)

Author keywords

Ab initio calculations; Heterocyclic compounds; Nonlinear optics; Tautomerism; Valence bond model

Indexed keywords

CALCULATIONS; CHEMICAL BONDS; ISOMERS; OPTICAL PROPERTIES; PLANTS (BOTANY);

AB INITIO CALCULATIONS; HETEROCYCLIC COMPOUND; NON-LINEAR OPTICAL PROPERTIES; NONLINEAR OPTICAL PROCESS; NONLINEAR OPTICAL RESPONSE; NUCLEAR CONFIGURATION; TAUTOMERISM; VALENCE BOND MODELS;

NONLINEAR OPTICS;

EID: 77949314613     PISSN: 14394235     EISSN: 14397641     Source Type: Journal    
DOI: 10.1002/cphc.200900616     Document Type: Article

References (29)

1. S. R. Marder, Chem. Commun. 2006, 131-134;
2. Nonlinear Optical Properties of Organic Molecules and Crystals (Eds. D. S. Chemla, J. Zeiis), Academic Press, New York, 1987;
3. Introduction to Nonlinear Optical Effects in Molecules and Polymers (Eds. P. N. Prasad, D. J. Williams), Wiley, New York, 1991;
4. Molecular Nonlinear Optics: Materials, Physics and Devices (Ed. J. Zeiss), Academic Press, New York, 1994;
5. Nonlinear Optics of Organic Molecules and Polymers (Eds. H. S. Nalva, M. Miyata), CRC, New York, 1997.
6. E. Kleinpeter, A. Koch, B. Mikhova, B. A. Stamboliyska, T. M. Kolev, Tetrahedron Lett. 2008, 49, 1323-1327.
7. F. Terenziani, G. D'Avino, A. Painelli, ChemPhysChem 2007, 8, 2433-2444.
8. A. Molinos-Gómez, X. Vidal, M. Maym, D. Velasco, J. Martorell, F. L pez-Calahorra, Tetrahedron 2005, 61, 9075-9081.
9. A. Abbotto, L. Beverina, R. Bozio, A. Facchetti, A. Ferrante, G. A. Pagani, D. Pedron, R. Signorini, Org. Lett. 2002, 4, 1495-1498.
10. R. Faure, J. Elguero, E. J. Vincent, R. Lazar, Org. Magn. Reson. 1978, 11, 617-621;
11. A. Avellaneda, M. Robin, R. Faure, A. P richaud, J.-P Galy, Magn. Reson. Chem. 2002, 40, 545-548;
12. F. Delmas, A. Avellaneda, C. Di Giorgio, M. Robin, E. De Clerq, P. Timon-David, J. P. Galy, Eur. J. Med. Chem. 2004, 39, 685-690.
13. S. Shaik, A. Shurki, D. Danovich, P. C. Hiberty, Chem. Rev. 2001, 101, 1501-1539;
14. A. Shurki, P. C. Hiberty, F. Dijkstra, S. J Shaik, J. Phys. Org. Chem. 2003, 16, 731-745.
15. G. Chen, D. Lu, W. A. Goddard III, J. Chem. Phys. 1994, 101, 5860-5864;
16. D. Lu, G. Chen, J. W. Perry, W. A. Goddard III, J. Am. Chem. Soc. Phys. 1994, 101, 4920-4930.
17. M. W. Hooper, M. Utsunomiya, J. F. Hartwing, J. Org. Chem. 2003, 68, 2861-2873.
18. J. Rosevear, J. F. K. Wilshire, Aust. J. Chem. 1981, 34, 839-853.
19. B. Ambati, V. Anand, P. Hanumanthu, Synt. Comm. 1997, 27, 1487-1493.
20. L. Salem, Electrons in Chemical Reactions: First Principles, John Wiley & sons, New York, 1982, Chapter 3.
21. W. J. Stevens, H. Basch, M. Krauss, J. Chem. Phys. 1984, 81, 6026-6033;
22. for Hatoms from A. Schafer, H. Horn, R. Ahlrichs, J. Chem. Phys. 1992, 97, 2571-2577.
23. J. Pipek, P. Z. Mezey, J. Chem. Phys. 1989, 90, 4916-4926.
24. The existence of these birradical states is currently under study.
25. M. W. Schmidt, K. K. Baldridge, J. A. Boatz, S. T. Elbert, M. S. Gordon, J. H. Jensen, S. Koseki, N. Matsunaga, K. A. Nguyen, S. Su, T. L. Windus, M. Dupuis, J. A. Montgomery Jr, J. Comput. Chem. 1993, 14, 1347-1363.
26. Ph. Durand, J. P. Malrieu in Advances in Chemical Physics; Ab Initio Methods in Quantum Chemistry. Part I; (Ed. K. P. Lawley), Wiley, Chichester, 1987, pp. 321-412.
27. J. L. Oudar, J. Chem. Phys. 1977, 67, 446-457.
28. J. L. Oudar, D. S. Chemla, J. Chem. Phys. 1977, 66, 2664-2668.
29. Notice that in the previous work,[4] the NMR spectra of compound 2 were registered in the presence of trifluoroacetic acid (TFA) due to solubility problems. This fact affects the tautomeric equilibrium.