Two ground state conformers of the proton sponge 1,8- bis(dimethylamino)naphthalene revealed by fluorescence spectroscopy and ab initio calculations

Journal of the American Chemical Society

Volumn 120, Issue 19, 1998, Pages 4840-4844

  Szemik Hojniak, A ^a   Zwier, J M ^b   Buma, W J ^b   Bursi, R ^c   Van Der Waals, J H ^d  

^a UNIVERSITY OF WROC AW   (Poland)

^b UNIVERSITY OF AMSTERDAM   (Netherlands)

^c NV ORGANON   (Netherlands)

^d LEIDEN UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

1,8 BIS(DIMETHYLAMINO)NAPHTHALENE; PROTON; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; FLUORESCENCE SPECTROSCOPY; MOLECULAR STABILITY;

EID: 0032550662     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja974245w     Document Type: Article

References (23)

1. Staab, H. A.; Saupe, T. Angew. Chem., Int. Ed. Engl. 1988, 27, 865.
2. Alder, R. W. Chem. Rev. 1989, 89, 1215.
3. Hibbert, F. J. J. Chem. Soc., Perkin. Trans. 1974, 2, 1862.
4. Lou, Yan K.; Saluja, P. P. S.; Kebarle, P.; Alder, R. W. J. Am. Chem. Soc. 1978, 100, 7328.
5. Perakyla, M. J. Org. Chem. 1996, 61, 7420.
6. Pyzalska, D.; Pyzalski, R.; Borowiak, T. J. Crystallogr. Spectrosc. Res. 1983, 13, 211.
7. Brzezinski, B.; Glowiak, T.; Grech, E.; Malarski, Z.; Sawka-Dobrowolska, W.; Sobczyk, L. J. Mol. Struct. 1993, 299, 1.
8. Alder, R. W. Tetrahedron 1990, 46, 683.
9. Llamaz-Saiz, A. L.; Foces-Foces, C.; Elguero, J. J. Mol. Struct. 1992, 273, 183.
10. Bakshi, P. K.; Cameron, T. S.; Knop, O. Can. J. Chem. 1996, 74, 201.
11. Brzezinski, B.; Glowiak, T.; Grech, E.; Malarski, Z.; Sobczyk, L. Croat. Chem. Acta 1992, 65, 101.
12. Einspar, H.; Robert, J. B.; Marsh, R. E.; Roberts, J. D. Acta Crystallogr. 1973, B29, 1611.
13. Platts, J. A.; Howard, S. T.; Wozniak, K. J. Org Chem. 1995, 59, 4647.
14. Szemik-Hojniak, A.; Rettig, W.; Herbich, J.; van der Waals, J. H.; Allonas, X. To be submitted for publication.
15. Unpublished results.
16. Wegewijs, B. R, Ph.D. Thesis, University of Amsterdam, 1994.
17. Zwier, J. M.; Wiering, P. G.; Brouwer, A. M.; Bebelaar, D.; Buma, W. J. J. Am. Chem. Soc. 1997, 119, 11523.
18. Grassian, V. H.; Warren, J. A.; Bernstein, E. R.; Secor, H. V. J. Chem. Phys. 1989, 90, 3994.
19. Johnson, J. R.; Jordan, K. D.; Plusquellic, D. F.; Pratt, D. W. J. Chem. Phys. 1990, 93, 2258.
20. Szemik-Hojniak, A.; Hanuza, J.; Bursi, R.; Buma, W. J.; van der Waals, J. H. To be submitted for publication.
21. Gaussian 94, Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Reprogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Head-Gordon, M.; Gonzales, C.; Pople, J. A., Gaussian Inc.: Pittsburgh, PA, 1995.
22. Boggs, J. E.; Niu, Z. J. Comp. Chem. 1985, 6, 46.
23. Bock, C. W.; George, P.; Trachtman, M. Theor. Chim. Acta 1986, 69, 235.