Structures and properties of tris(donor)-tris(acceptor)-substituted benzenes, 8: On the balance of steric, electronic and hydrogen bond effects in 1,3,5-tris(amino)-2,4,6-tris(acceptor)-substituted benzenes

Liebigs Annales

Volumn , Issue 7, 1996, Pages 1175-1182

  Wolff, J Jens ^a   Gredel, Frank ^a   Hillenbrand, Daniela ^a   Irngartinger, Hermann ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Benzene ring, distortion of; Benzene, donor acceptor substituted; Conformational analysis; Non linear optics

Indexed keywords

EID: 33749152979     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (38)

1. R. Wortmann, C. Glania, P. Krämer, R. Matschiner, J. J. Wolff, S. Kraft, B. Treptow, E. Barbu, D. Hillenbrand, D. Längle, J. Am. Chem. Soc., submitted.
2. Part 6: T. Verbiest, K. Clays, C. Samyn, J. J. Wolff, D. Reinhoudt, A. Persoons, J. Am. Chem. Soc., ibid. 1994, 116, 9320.
3. [2a] P. N. Prasad, D. J. Williams, Nonlinear Optical Effects in Molecules and Polymers, Wiley, New York, 1991.
4. [2b] S. R. Marder, J. E. Sohn, G. D. Stucky, (Eds.) Materials for Nonlinear Optics, ACS Symposium Series 455, American Chemical Society, Washington, 1991.
5. [2c] S. R. Marder, L.-T. Cheng, B. G. Tiemann, A. C. Friedli, M. Blanchard-Desce, J. W. Perry, J. Skindhøj, Science 1994, 263, 511, and references cited.
6. [3a] P. D. Maker, Phys. Rev. A 1970, 1, 923.
7. [3b] D. S. Chemla, J. L. Oudar, J. Jerphagnon, Phys. Rev. B 1975, 12, 4534.
8. [3c] J. L. Brédas, F. Meyers, B. M. Pierce, J. Zyss, J. Am. Chem. Soc. 1992, 114, 4928.
9. [3d] M. Joffre, D. Yaron, R. J. Silbey, J. Zyss, J. Chem. Phys. 1992, 97, 5607.
10. [4a] J. J. Wolff, S. F. Nelsen, P. A. Petillo, D. R. Powell, Chem. Ber. 1991, 124, 1719.
11. [4b] J. J. Wolff, S. F. Nelsen, D. R. Powell, J. M. Desper, Chem. Ber. 1991, 124, 1727.
12. [4c] J. J. Wolff, S. F. Nelsen, D. R. Powell, J. Org. Chem. 1991, 56, 5908.
13. [4d] J. J. Wolff, S. F. Nelsen, D. R. Powell, B. Nuber, Angew. Chem. 1992, 104, 899;
14. Angew. Chem. Int. Ed. Engl. 1992, 31, 882.
15. [4e] J. J. Wolff, H. Irngartinger, F. Gredel, I. Bolocan, Chem. Ber. 1993, 126, 2127.
16. [4f] A. Zietsch, Diplomarbeit, Universität Heidelberg, 1993.
17. [4g] Structural distortions of aromatic systems have been treated extensively by Dähne: S. Dähne, Chimia 1991, 45, 288, and refs. cited.
18. [5a] J. M. Chance, B. Kahr, A. B. Buda, J. S. Siegel, J. Am. Chem. Soc. 1989, 111, 5940.
19. [5b] K. K. Baldridge, J. S. Siegel, J. Am. Chem. Soc. 1993, 115, 10782.
20. H. H. Cady, A. C. Larson, Acta Crystallogr. 1965, 18, 485.
21. I. N. Levine, Quantum Chemistry, 4th ed., Prentice Hall, Englewood Cliffs, New Jersey, 1991, p. 604, and references therein.
22. G. Scheibe, W. Seiffert, H. Wengenmayr, C. Jutz, Ber. Bunsenges. Phys. Chem. 1963, 67, 560.
23. Cf., however, amine exchange in 1-dialkylamino-2,4-dinitronaphthalenes: S. Sekiguchi, T. Suzuki, M. Hosokawa, J. Chem. Soc., Perkin Trans. 2, 1989, 1783.
24. F. Terrier, Nucleophilic Aromatic Displacement: The Influence of the Nitro Group, VCH, New York, 1991, pp. 4ff.
25. Expectation values for C-C bond lengths: 1.39-1.40 Å (F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, R. Taylor, J. Chem. Soc., Perkin Trans. 2, 1987, S1).
26. C-N in hexakis(dimethylamino)benzene: 1.440 Å (J. M. Chance, B. Kahr, A. B. Buda, J. P. Toscano, K. Mislow, J. Org. Chem. 1988, 53, 3226).
27. C-N in 1,3,5-trinitrobenzene: 1.480 Å (C. S. Choi, J. E. Abel, Acta Crystallogr., Sect. B, 1972, 28, 193).
28. J. R. Holden, Acta Crystallogr. 1967, 22, 545.
29. P. C. Hiberty, G. Ohanessian, J. Am. Chem. Soc. 1984, 106, 6963;
30. R. D. Topsom, Progr. Phys. Org. Chem. 1987, 16, 85;
31. J. R. Holden, C. Dickinson, J. Phys. Chem. 1977, 81, 1505.
32. J. J. P. Stewart, J. Comput. Chem. 1989, 10, 221.
33. Further details of the crystal structure determinations are available on request from the Fachinformationszentrum Karlsruhe, D-76344 Eggenstein-Leopoldshafen, on quoting the depository numbers CSD-405035 2{1,1,0}, -405036 4{2,1,1}, -405037 2{2,0,0}, -405038 5{2,2,1}, -405039 4{2,2,0}, -405040 1{1,0,0}, -405041 3{2,1,0}, the names of the authors, and the journal citation. All structures were solved by the use of direct methods: SIR88 (M. C. Burla, M. Camalli, G. Cascarano, G. Giacovazzo, G. Polidori, R. Spagna, D. Viterbo, J. Appl. Crystallogr. 1989, 22, 389) and SHELXS-86
34. (G. M. Sheldrick, Acta Crystallogr., Sect. A, 1990, 46, 467).
35. Chemische Fabrik Griesheim (Inv.: P. Engelbertz), D.R.P. 767510 (1936) [Chem. Abstr. 1955, 49, 14803d];
36. M. E. Hill, F. Taylor, Jr., J. Org. Chem. 1960, 25, 1037. For the latter procedure, 266.5 g of oleum is required, not 266.5 ml, as written.
37. W. M. Koppes, G. W. Lawrence, M. E. Sitzmann, H. G. Adolph, J. Chem. Soc., Perkin Trans. 1, 1981, 1815.
38. B. Flürscheim, E. L. Holmes, J. Chem. Soc. 1928, 3041.