Abstract
Tetramethylsilane (TMS) can be included by β-cyclodextrin (β-CD), and sodium 2,2-dimethylsilapentane-5-sulphonate (DSS) can form inclusion complexes with β- and γ-CD. The NMR chemical shifts are changed considerably as a result of the strong interaction between CD and the guest compound in the inclusion complexes. A downfield shift of as much as 0.63 ppm shift downfield has been observed for the protons of external TMS in CD aqueous solution. In view of this, the question arises of whether TMS and DSS can be used as internal references. DSS in D2O is suggested as an external reference for aqueous cyclodextrin solution in NMR measurements.
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References
M.L. Bender and M. Komiyama:Cyclodextrin Chemistry, Springer, New York (1978).
W. Saenger:Angew. Chem. Int. Ed. Engl. 19, 344 (1980).
I. Tabushi:Acc. Chem. Res. 15, 66 (1982).
J. Szejtli:Cyclodextrins and Their Inclusion Complexes, Akademiac Kiado, Budapest (1982).
J. Szejtli:Cyclodextrin Technology, Kluwer Academic Publishers, Dordrecht (1988).
M. Sakurai, H. Hoshi, Y. Inoue, and R. Chujo:Chem. Phys. Lett. 163, 217 (1989).
K. Harata, F. Hirayama, K. Uckama, and G. Tsoucaris:Chem. Lett. 1585 (1988).
C. Bentzel, W. Saenger, B.E. Hingerty, and G.M. Brown:J. Am. Chem. Soc. 106, 7545 (1984).
B. Isnin, C. Salam, and A.E. Kaifer:J. Org. Chem. 56, 35 (1991).
V.K. Smith, T.T. Ndou, A.M. de Pena, and I.M. Warner:J. Incl. Phenom. 10, 471 (1991).
R. Fornasier, M. Parmagnani, and U. Tonellato:J. Incl. Phenom. 11, 225 (1991); J. Lehmann, E. Kleinpeter, and J. Krechl:ibid. 10, 233 (1991).
M. Suzuki, H. Takai, J. Szejti, and E. Fenyvesi:Carbohydr. Res. 201, 1 (1990).
O. Bekers, J.J.K.D. Bosch, S.P. van Heldem, D. Seijkens, J.H. Beijnen, A. Bult, and W.J.M. Underberg:J. Incl. Phenom. 11, 185 (1991).
F. Djedaini and B. Perly:J. Mol. Struct. 239, 161 (1990).
C.M. Spencer, J.F. Stoddart, and R. Zarzycki:J. Chem. Soc., Perkin Trans. 2, 1323 (1987).
J.C. Christofides, D.B. Davies, J.A. Martin, and E.B. Rathbone:J. Am. Chem. Soc. 108, 5738 (1986).
C. Jaime, J. Redondo, F. Sanchez-Ferrando, and A. Virgili:J. Org. Chem. 55, 4772 (1990).
M. Suzuki and Y. Sasaki:Chem. Pharm. Bull. 27, 609 (1979).
A. Buvabi and L. Barcza:Acta Chimica Hungarica 126, 455 (1989); R.J. Bergeron, M.A. Channing, G.J. Gibeily, and D.M. Pillor:J. Am. Chem. Soc. 99, 5416 (1977).
N.J. Turro, T. Okubo, and C.-T. Chung:J. Am. Chem. Soc. 104, 1789 (1982).
E.D. Becker:High Resolution NMR: Theory and Chemical Applications, 2nd Ed., Academic Press (1980).
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Li, ZZ., Guo, QX., Ren, T. et al. Can TMS and DSS be used as NMR references for cyclodextrin species in aqueous solution?. Journal of Inclusion Phenomena and Molecular Recognition in Chemistry 15, 37–42 (1993). https://doi.org/10.1007/BF00706472
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DOI: https://doi.org/10.1007/BF00706472