Abstract
The inclusion complexes of the carboxylate forms of 3-carboxy-(I) and 2-carboxy-phenoxathiin (II) with β-cyclodextrin were studied by bothone- and two-dimensional NMR spectroscopy. The analysis of the induced chemical shifts of theguests in the presence of different amounts of the host indicates the formation of complexes with 1:1stoichiometry and association averaged pK values of 3.75 (I) and 4.4 (II). Thequalitative analysis of cross peaks in the ROESY spectra support the inclusion of the guests in the cavitywith the substituted phenyl ring, the COO- group being in the proximity of the primary rim.
Similar content being viewed by others
References
S. Ionescu, D. Gavriliu, O. Maior and M. Hillebrand: J. Photochem. Photobiol. 124, 67 (1999).
J. Szejtli and T. Osa: Cyclodextrins, in J.M. Lehn (ed.), Comprehensive Supramolecular Chemistry, Vol. 3, Pergamon (1997), pp. 1-180.
B. Chankvetadze, G. Blaschke and G. Pintore: Ligand-cyclodextrins complexes, in U. Holzgrabe, I. Wawer and B. Diehl (eds.), NMR Spectroscopy in Drug Development and Analysis, Wiley-VCH (1999), pp. 154-174.
H.-J. Schneider, F. Hacket and V. Rudiger: Chem. Rev. 98, 1755 (1998).
M. Oana, A. Tintaru, D. Gavriliu, O. Maior and M. Hillebrand: J. Phys. Chem. B 106, 257 (2002).
D. Neuhaus and M.P. Williamson: The Nuclear Overhauser Effect in Structural and Conformational Analysis, Wiley-VCH (2000), pp. 274-276.
O. Maoir and D. Gavriliu: Rev. Chim. (Buc.) 47, 127 (1996).
A. Orstan and J.B. Ross: J. Phys. Chem. 91, 2739 (1987).
H. Dodziuk, A. Ejchart, O. Lukin, and M. Vysotsky: J. Org. Chem. 64, 1503 (1999).
H. Desvaux, B. Berthault, N. Birlirakis, N. Goldman and M. Piotto: J. Magn. Reson. A 113, 47 (1994).
P. Salvadori, G. Uccello-Barretta, F. Balzano, C. Bertucci and C. Chiavacci: Chirality 8, 423 (1996).
M. Piotto, V. Saudek and V. Sklenar: J. Biomol. NMR 2, 661 (1992).
V. Sklenar, M. Piotto, R. Leppik and V. Saudek: J. Magn. Reson. A 102, 241 (1993).
R.S. Macomber: J. Chem. Educ. 69, 375 (1992).
S. Florea, H.O. Kalinowski, O. Maior and D. Gavriliu: Polish. J. Chem. 70, 36 (1996).
M.E. Amato, G.M. Lombardo, G.C. Pappalardo and G. Scarlata: J. Mol. Struct. 350, 71 (1995).
E. Butkus, J.C. Martins and U. Berg: J. Incl. Phenom. Mol. Recogn. 25, 125 (1996).
D. Salvatierra, C. Jaime, A. Virgili and F. Sanchez-Ferrando: J. Org. Chem. 61, 9578 (1996).
K. Eliadou, K. Yannakopoulou, A. Rontoyianny, and I.M. Mavridis: J. Org. Chem. 64, 6217 (1999).
E. Butkus, J.C. Martins and U. Berg: J. Incl. Phenom. Mol. Recogn. 26, 209 (1996).
M. Zubiaur and C. Jaime: J. Org. Chem. 65, 8139 (2000).
C. Pean, C. Creminon, A. Wijkhuisen, B. Perly and F. Djedaini-Pilard: J. Chim. Phys. 96, 1486 (1999).
M.E. Amato, K.B. Lipkowitz, G.M. Lombardo and G.C. Pappalardo: Magn. Reson. Chem. 36, 693 (1998).
A. Gadre, V. Rudiger, H.-J. Schneider and K.A. Connors: J. Pharm. Sci. 86, 236 (1997).
H. Hirai, Y. Shiraishi, H. Mihori, K. Saito and T. Kawamura: Polym. J. 28, 91 (1996).
M.V. Rekharsky and Y. Inoue: Chem. Rev. 98, 1875 (1998).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Tintaru, A., Hillebrand, M. & Thevand, A. NMR Study of the Inclusion Complexes of Carboxy-Phenoxathiin Derivatives with β-Cyclodextrin. Journal of Inclusion Phenomena 45, 35–40 (2003). https://doi.org/10.1023/A:1023044700449
Issue Date:
DOI: https://doi.org/10.1023/A:1023044700449