Aminopyrimidine-based donor-acceptor chromophores: Push-pull versus aromatic behaviour

European Journal of Organic Chemistry

Volumn , Issue 1, 2008, Pages 99-108

  Ortíz, Alejandro ^a,b   Insuasty, Braulio ^a   Torres, M Rosario ^b   Herranz, M Ángeles ^b   Martín, Nazario ^b   Viruela, Rafael ^c   Ortí, Enrique ^c  

^a UNIVERSIDAD DEL VALLE   (Colombia)

^b UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^c UNIVERSITY OF VALENCIA   (Spain)

Author keywords

2 Aminopyrimidines; Aromaticity; Nonplanar; Push pull

Indexed keywords

EID: 84961982005     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700718     Document Type: Article

References (46)

1. a) Special issue dedicated to aromaticity, see: P. v. R. Schleyer, Chem. Rev. 2001, 101, 1115-1566;
2. b) Special issue dedicated to aromaticity, see: P. v. R. Schleyer, Chem. Rev. 2005, 105, 3433-3947.
3. a) R. Herges, Chem. Rev. 2006, 106, 4820-4842;
4. b) D. Ajami, O. Oeckler, A. Simon, R. Herges, Nature 2003, 426, 819-821;
5. c) see also: International Symposium on Novel Aromatic Compounds (ISNA-12), Awaji-Island, Japan, July 2007.
6. a) G. M. Blackburn, M. J. Gait, Nucleic Acids in Chemistry and Biology, Oxford University Press, Oxford, 1996;
7. b) J. S. Kwiatkowski, B. Pulmann, Adv. Heterocycl. Chem. 1975, 18, 199-335;
8. c) A. Alparone, A. Millefiori, S. Millefiori, Chem. Phys. 2005, 312, 261-274.
9. A. El-Ghayoury, A. P. H. J. Schenning, P. A. Van Hal, J. K. J. Van Duren, R. A. J. Janssen, E. W. Meijer, Angew. Chem. 2001, 113, 3772-3775;
10. Angew. Chem. Int. Ed. 2001, 40, 3660-3663.
11. Y. J. Kim, J. H. Kim, M.-S. Kang, M. J. Lee, J. Won, J. Ch. Lee, Y. S. Kang, Adv. Mater. 2004, 16, 1753-1757.
12. Ch.-H. Huang, N. D. McClenaghan, A. Kuhn, G. Bravic, D. M. Bassani, Tetrahedron 2006, 62, 2050-2059.
13. T. Hegmann, J. Kain, S. Diele, B. Schubert, H. Bögel, C. Tschierske, J. Mater. Chem. 2003, 13, 991-1003.
14. For a review, see: T. Verbiest, S. Houbrechts, M. Kauranen, K. Clays, A. Persoons, J. Mater. Chem. 1997, 7, 2175-2189.
15. E. Botek, F. Castet, B. Champagne, Chem. Eur. J. 2006, 12, 8687-8695.
16. E. M. Priego, L. Sánchez, M. A. Herranz, N. Martín, R. Viruela, E. Ortí, Org. Biomol. Chem. 2007, 5, 1201-1209.
17. T. J. Thomas, R. Otteman, Heterocycles 1983, 20, 1805-1809.
18. J. S. Chappell, A. N. Bloch, W. A. Bryden, M. Maxfield, T. O. Poehler, D. O. Cowan, J. Am. Chem. Soc. 1981, 103, 2442-2443.
19. P. De la Cruz, N. Martín, F. Miguel, C. Seoane, A. Albert, F. H. Cano, A. Gonzalez, J. M. Pingarrón, J. Org. Chem. 1992, 57, 6192-6198.
20. N. Martín, J. L. Segura, C. Seoane, P. de la Cruz, F. Langa, E. Ortí, R. Viruela, P. M. Viruela, J. Org. Chem. 1995, 60, 4077-4084.
21. E. Ortí, R. Viruela, P. M. Viruela, J. Phys. Chem. 1996, 100, 6138-6146.
22. a) N. Martín, M. Hanack, J. Chem. Soc. Chem. Commun. 1988, 1522-1524;
23. b) N. Martín, R. Behnisch, M. Hanack, J. Org. Chem. 1989, 54, 2563-2568.
24. G. M. Sheldrick, SHELX97, Program for Refinement of Crystal Structure, University of Göttingen, Göttingen, Germany, 1997.
25. L. Fernholt, C. Romming, Acta Chem. Scand. Ser. A 1978, 32, 271-273.
26. Harmonic frequency calculations on the optimized geometries confirmed the four structures as minima of the potential energy hypersurface, as no imaginary frequency was obtained.
27. T. Michinobu, C. Boudon, J.-P. Gisselbrecht, P. Seiler, B. Frank, N. N. P. Moonen, M. Gross, F. Diederich, Chem. Eur. J. 2006, 12, 1889-1905.
28. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman Jr, J. A. Montgomery, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, G. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03, Revision C.02, Gaussian, Inc., Wallingford CT, 2004.
29. A. D. Becke, J. Chem. Phys. 1993, 98, 1372-1377.
30. a) M. M. Francl, W. J. Pietro, W. J. Hehre, J. S. Binkley, M. S. Gordon, D. J. Defrees, J. A. Pople, J. Chem. Phys. 1982, 77, 3654-3665;
31. b) W. J. Hehre, L. Radom, P. v. R. Schelyer, J. A. Pople, Ab initio Molecular Orbital Theory, Wiley, New York, 1986.
32. a) E. Runge, E. K. U. Gross, Phys. Rev. Lett. 1984, 52, 997-1000;
33. b) E. K. U. Gross, W. Kohn, Adv. Quantum Chem. 1990, 21, 255-291;
34. c) E. K. U. Gross, C. A. Ullrich, U. J. Gosssman, Density Functional Theory (Eds.: E. K. U. Gross, R. M. Driezler), Plenum Press, New York, 1995, p. 149;
35. d) M. E. Casida, Recent Advances in Density Functional Methods, Part I (Ed.: D. P. Chong), World Scientific, Singapore, 1995, p. 155.
36. a) A. E. Reed, F. Weinhold, J. Chem. Phys. 1983, 78, 4066-4073;
37. b) A. E. Reed, R. B. Weinstock, F. Weinhold, J. Chem. Phys. 1985, 83, 735-746.
38. A. E. Reed, L. A. Curtiss, F. Weinhold, Chem. Rev. 1988, 88, 899-926.
39. a) J. Tomasi, M. Persico, Chem. Rev. 1994, 94, 2027-2094;
40. b) C. S. Cramer, D. G. Truhlar, Solvent Effects and Chemical Reactivity (Eds.: O. Tapia, J. Bertrán), Kluwer, Dordrecht, 1996, p. 1.
41. a) S. Miertus, E. Scrocco, J. Tomasi, Chem. Phys. 1981, 55, 117-129;
42. b) S. Miertus, J. Tomasi, Chem. Phys. 1982, 65, 239-245;
43. c) M. Cossi, V. Barone, R. Cammi, J. Tomasi, Chem. Phys. Lett. 1996, 255, 327-335;
44. d) E. Cances, B. Mennucci, J. Tomasi, J. Chem. Phys. 1997, 107, 3032-3041;
45. e) V. Barone, M. Cossi, J. Tomasi, J. Comput. Chem. 1998, 19, 404-417;
46. f) M. Cossi, G. Scalmani, N. Rega, V. Barone, J. Chem. Phys. 2002, 117, 43-54.