Abstract
The preferred conformations in solution for substituents onsym-dibenzo-14-crown-4 ethers are shown by NMR to depend on the atom, carbon or oxygen, linking the substituent to the crown ring.
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Y. Kudo, Y. Takeda, K. Hiratani, and H. Matsuda:Anal. Sci. 7, 549 (1991).
R. Kataky, P.E. Nicholson, and D. Parker:J. Chem. Soc., Perkin Trans. 2, 321 (1990).
K. Kimura, S. Iketani, H. Sakamoto, and T. Shono:Analyst 115, 1251 (1990).
Y. Nakatsuji, R. Wakita, Y. Harada, and M. Okhara:J. Org. Chem. 54, 2988 (1989).
H. Sakamoto, K. Kimura, M. Tanaka, and T. Shono:Bull. Chem. Soc. Jpn. 62, 3394 (1989).
E. Uhlemann, H. Bukowsky, F. Dietrich, K. Gloe, P. Muhl and H. Mosler:Anal. Chim. Acta 224, 47 (1989).
K. Wilcox and G. E. Pacey:Talanta 38, 1315 (1991).
R. A. Sachleben and J. H. Burns:J. Chem. Soc., Perkin Trans 2 1971 (1992).
N. K. Dalley, W. M. Jiang, and U. Olsher:J. Incl. Phenom. 12, 305 (1992).
G. Shoham, D. W. Christianson, R. A. Bartsch, G. S. Heo, U. Olsher, and W. N. Lipscomb:J. Am. Chem. Soc. 116, 1280 (1984).
U. Olsher, F. Frolow, R. A. Bartsch, M. J. Pugia, and G. Shoham:J. Am. Chem. Soc. 111, 9217 (1989).
R. A. Bartsch, B. P. Czech, S. I. Kang, L. E. Stewart, W. Walkowiak, W. A. Charewicz, G. S. Heo, and B. Son:J. Am. Chem. Soc. 107, 4997 (1985).
Y. Habata, M. Ikeda, and S. Akabori:Tetrahedron Lett. 33, 3157 (1992).
R. A. Bartsch:Solvent Extr. Ion Exch. 7, 829 (1989).
J. H. Burns and R. A. Sachleben:Inorg. Chem. 27, 1787 (1988).
J. H. Burns and R. A. Sachleben:Inorg. Chem. 29, 788 (1990).
J. H. Burns and R. A. Sachleben:Acta Crystallogr., Sect. C 47, 2339 (1991).
R. A. Sachleben and J. H. Burns:Acta Crystallogr., Sect. C 47, 1968 (1991).
U. Olsher, F. Frolow, N. K. Dalley, J. Weiming, Z.-Y. Yu, J. M. Knobeloch, and R. A. Bartsch:J. Am. Chem. Soc. 113, 6750 (1991).
H. Schneider and V. Hoppen:Tetrahedron Lett. 579 (1974).
Carbon-13 and proton NMR spectra were recorded on a Bruker MSL-400 spectrometer operating at 100.613 and 400.13 MHz, respectively. 0.1 M crown ether solutions in CDCl3 for13C and in toluene-d8 for1H were studied at 303K.
NOESY spectra were performed in the phase-sensitive mode with a mixing time of 700 ms at 303K. The spectra were recorded by using 256×1K data points with zero-filling to 1K×1K data points.
R.J. Abraham and G. Gatti:J. Chem. Soc. B 961 (1969).
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Chen, Z., Sachleben, R.A. Conformational analysis of substituted dibenzo-14-crown-4 ethers in solution by 1D and 2D NMR. J Incl Phenom Macrocycl Chem 16, 91–95 (1993). https://doi.org/10.1007/BF00708765
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DOI: https://doi.org/10.1007/BF00708765