Structural characterization of the Brooker's merocyanine/β-cyclodextrin complex using NMR spectroscopy and molecular modeling

Journal of Molecular Structure

Volumn 965, Issue 1-3, 2010, Pages 31-38

  Holt, Jennifer S ^a  

^a BEHREND COLLEGE   (United States)

Author keywords

Cyclodextrin; Brooker's merocyanine; Complexation induced shifts; Isomerization; ONIOM; Theoretical modeling

Indexed keywords

B3LYP/6-31G; BROOKER'S MEROCYANINE; CIS AND TRANS ISOMERS; CIS-TO-TRANS ISOMERIZATION; CYCLODEXTRIN CAVITIES; DYE MOLECULE; MEROCYANINE; NEUTRAL MOLECULES; NMR SPECTROSCOPY; ONIOM; OPTIMIZED STRUCTURES; PLANARITY; PM3 METHOD; SEMI-EMPIRICAL; STABLE COMPLEXES; STRUCTURAL CHARACTERIZATION; THEORETICAL MODELING; THEORETICAL VALUES; TRANS ISOMERS;

BINDING ENERGY; ELECTRON TRANSITIONS; MOLECULAR MODELING; MOLECULES; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOISOMERIZATION; THERMODYNAMIC PROPERTIES; WATER ANALYSIS;

ISOMERS;

EID: 74849132985     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2009.11.034     Document Type: Article

References (39)

1. Steed J.W., and Atwood J.L. Supramolecular Chemistry (2000), John Wiley & Sons, Ltd., Chichester, England
2. Duveneck G.L., Sitzmann E.V., Eisenthal K.B., and Turro N.J. J. Phys. Chem. 93 (1989) 7166
3. Brooker L.G.S., Keyes C.H., Sprague R.H., Van Dyke R.H., Van Zandt E., White F.L., Cressman H.W.J., and Dent S.G. J. Am. Chem. Soc. 73 (1951) 5332
4. Brooker L.G.S., Keyes C.H., and Heseltine D.W. J. Am. Chem. Soc. 73 (1951) 5350
5. Da Silva D.C., Ricken I., Silva M.A.d.R., and Machado V.G. J. Phys. Org. Chem. 15 (2002) 420
6. Catalan J., Meno E., Meutermans W., and Elguero J. J. Phys. Chem. 96 (1992) 3615
7. De Ridder D.J.A., Heijedrijk D., Schenk H., Dommisse R.A., Lemiere G.L., Lepoivre J.A., and Alderweireldt F.A. Acta Crystallogra., Sect. C: Crys. Struct. Commun. 46 (1990) 2197
8. Gains G.L. Angew. Chem. 99 (1987) 346
9. Steiner U., Abdel-Kader M.H., Fisher P., and Kramer H.E.A. J. Am. Chem. Soc. 100 (1978) 3190
10. Abdel-Kamer M.H., and Steiner U. J. Chem. Educ. 60 (1983) 160
11. Abdel-Halim S.T., Abdel-Kamer M.H., and Steiner U. J. Phys. Chem. 92 (1988) 4324
12. Holt J.S., Campitella A., Rich A., and Young J.L. J. Incl. Phenom. Macrocycl. Chem. 61 (2008) 251
13. Oesterhelt D., and Stoeckenius W. Proc. Nat. Acad. Sci. USA 70 (1973) 2853
14. Davis W.B., Svec W.A., Ratner M.A., and Wasielewski M.R. Nature 396 (1998) 60
15. Hamasaki K., Nakamura A., Ueno A., and Toda F. J. Incl. Phenom. Mol. Rec. Chem. 13 (1992) 349
16. Stewart J.J.P. J. Comp. Chem. 10 (1989) 209
17. Stewart J.J.P. J. Comp. Chem. 10 (1989) 221
18. Dapprich S., Komaromi I., Byun K.S., Morokuma K., and Frisch M.J. J. Mol. Struct. (Theochem) 1 (1999) 461
19. Yan C., Xiu Z., Li X., Teng H., and Hao C. J. Incl. Phenom. Macrocycl. Chem. 58 (2007) 337
20. Suzuki M., Ito K., Fushimi C., and Kondo T. Chem. Pharm. Bull. 41 (1993) 942
21. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. 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, 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.
22. Steiner T., and Koellner G. J. Am. Chem. Soc. 116 (1994) 5122
23. Ohashi M., Kasatani K., Shinohara H., and Sato H. J. Am. Chem. Soc. 112 (1990) 5824
24. Lee C.T., Yang W.T., and Parr R.G. Phys. Rev. B 37 (1988) 785
25. Li G., and McGown L.B. Science 264 (1994) 249
26. Cacialli F., Wilson J.S., Michels J.J., Daniel C., Silva C., Friend R.H., Severin N., Samori P., Rabe J.P., O'Connell J.M., Taylor P.N., and Anderson H.L. Nat. Mater. 1 (2002) 160
27. Tomasi J., Mennucci B., and Cammi R. Chem. Rev. 105 (2005) 2999
28. Balabai N., Linton N., Napper A., Priyadarshy S., Sukharevsky A.P., and Waldeck D.H. J. Phys. Chem. B 102 (1998) 9617
29. Schneider H.-J., Hacket F., Rüdiger V., and Ikeda H. Chem. Rev. 98 (1998) 1755
30. Demarco P.V., and Thakkar A.L. J. Chem Soc. Chem. Commun. 1 (1970) 2
31. Thakkar A.L., and Demarco P.V. J. Pharm. Sci. 60 (1971) 652
32. Salvatierra D., Jaime C., Virgili A., and Sanchez-Ferrando F. J. Org. Chem. 61 (1996) 9578
33. Morley J.O., Morley R.M., Docherty R., and Charlton M.H. J. Am. Chem. Soc. 119 (1997) 10192
34. Sakurai M., Kitagawa M., Hoshi H., Inoue Y., and Chujo R. Carbohydr. Res. 198 (1990) 181
35. Sousa S.F., Fernandes P.A., and Ramos M.J. J. Phys. Chem. A 111 (2007) 10439
36. Linderner K., and Saenger W. Carbohydr. Res. 99 (1982) 103
37. Zabel V., Saenger W., and Mason S.A. J. Am. Chem. Soc. 108 (1986) 3664
38. Lawtrakul L., Viernstein H., and Wolschann P. Int. J. Pharm. 256 (2003) 33
39. Heine T., Dos Santos H.F., Patchkovski S., and Duarte H.A. J. Phys. Chem. A 111 (2007) 5648