Abstract
New derivatives of p-tert-butylthiacalix[4]arene were synthesized. The conformation of the macrocycles and interproton distances in the synthesized thiacalix[4]arenes in solutions were determined by NMR spectroscopy. p-tert-Butylthiacalix[4]arene distally disubstituted at the lower rim adopts the cone conformation, and the tetrasubstituted products are formed in the 1,3-alternate conformation.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
T. M. Fyles and W. F. Van Straaten-Nijenhuis, Ion Channel Models, in Comprehensive Supramolecular Chemistry, Pergamon Press, Oxford, 1996, 10, 53.
M. Sugawara, A. Hirano, P. Buhlmann, and Y. Umezawa, Bull. Chem. Soc. Jpn., 2002, 75, 187.
I. I. Stoikov, I. S. Antipin, and A. I. Konovalov, Usp. Khim., 2003, 72, 1190 [Russ. Chem. Rev., 2003, 72, 1055 (Engl. Transl.)].
L. Jullien, T. Lazrac, J. Canceill, L. Lacombe, and J.-M. Lehn, J. Chem. Soc., Perkin Trans. 2, 1993, 1011.
M. J. Pregel, L. Jullien, J. Canceill, L. Lacombe, and J.-M. Lehn, J. Chem. Soc., Perkin Trans. 2, 1995, 417.
Y. Tanaka, Y. Kobuke, and M. Sokabe, Angew. Chem., Int. Ed. Engl., 1995, 34, 693.
A. Karlin and M. H. Akabas, Neuron, 1995, 15, 1231.
C. D. Gutsche, in Calixarenes, Ed. J. F. Stoddart, Royal Society of Chemistry, Cambridge, 1989, 225.
A. Ikeda and S. Shinkai, J. Am. Chem. Soc., 1994, 116, 3102.
A. Ikeda and S. Shinkai, Chem. Rev., 1997, 97, 1713.
V. Sidorov, F. W. Kotch, G. Abdrakhmanova, R. Mizani, J. C. Fettinger, and J. T. Davis, J. Am. Chem. Soc., 2002, 124, 2267.
F. W. Kotch, V. Sidorov, Y.-F. Lam, K. J. Kayser, H. Li, M. S. Kaucher, and J. T. Davis, J. Am. Chem. Soc., 2003, 125, 15140.
E. A. Shokova and V. V. Kovalev, Zh. Org. Khim., 2003, 39, 13 [Russ. J. Org. Chem., 2003, 39 (Engl. Transl.)].
Z. Asfari, V. Bohmer, J. Harrowfield, J. Vicens, and M. Saadioui, Calixarenes 2001, Kluwer Academic Press, Dordrecht, 2001, 683.
M. Pons and O. Millet, Progress in Nuclear Magnetic Resonance Spectroscopy, 2001, 38, 267.
Dynamic Nuclear Magnetic Resonance Spectroscopy, Eds L. M. Jackman and F. A. Cotton, Acad. Press, London, 1975, 660 p.
J. Sandstrom, Dynamic NMR Spectroscopy, Acad. Press, London, 1982, 226 p.
M. Oki, Application of Dynamic NMR Spectroscopy to Organic Chemistry, VCH Publishers, Inc., New York, 1985, 423 p.
R. R. Ernst, B. Bodenhausen, and A. Wokaun, Principles of Nuclear Magnetic Resonance in One and Two Dimensions, Oxford University Press, Oxford, 1987, 610 p.
Van der Ven and J. M. Frank, Multidimensional NMR in Liquids: Basic Principles and Experimental Methods, Wiley-VCH, Toronto, 1995, 399 p.
S. Macura and R. R. Ernst, Molecular Physics, 1980, 41, 95.
S. Macura, Y. Huang, D. Suter, and R. R. Ernst, J. Magn. Reson., 1981, 43, 259.
M. Kock and C. Griesinger, Angew. Chem., Int. Ed. Engl., 1994, 33, 332.
T. Geppert, M. Kock, M. Reggelin, and C. Griesinger, J. Magn. Reson., Ser. B, 1995, 107, 91.
V. V. Klochkov, F. Kh. Karatayeva, R. A. Shaikhutdinov, B. I. Khairutdinov, M.-A. Molins, and M. Pons, Appl. Magn. Reson., 2002, 22, 431.
T. A. Gadiev, B. I. Khairutdinov, R. A. Shaikhutdinov, and V. V. Klochkov, Novosti YaMR v pis’makh [NMR News in Letters], 2002, 2, 1435 (in Russian).
H. Kumagai, M. Hasegawa, S. Miyanari, Y. Sugawa, Y. Sato, T. Hori, S. Ueda, H. Kamiyama, and S. Miyano, Tetrahedron Lett., 1997, 38, 3971.
T. Sone, Y. Ohba, K. Moriya, H. Kumada, and K. Ito, Tetrahedron Lett., 1997, 53, 10689.
V. V. Klochkov, B. I. Khairutdinov, R. A. Shaikhutdinov, M. Findaisen, and S. Berger, Zh. Obshch. Khim., 2001, 71, 1339 [Russ. J. Gen. Chem., 2001, 71 (Engl. Transl.)].
T. A. Gadiev, B. I. Khairutdinov, R. A. Shaikhutdinov, F. Kh. Karatayeva, A. V. Aganov, V. V. Klochkov, M.-A. Molins, and M. Pons, Appl. Magn. Reson., 2003, 25, 347.
Author information
Authors and Affiliations
Additional information
__________
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2172–2178, October, 2004.
Rights and permissions
About this article
Cite this article
Stoikov, I.I., Ibragimova, D.S., Antipin, I.S. et al. New materials based on tubular nanodimensional structures 1. Synthesis, structural studies and determination of interproton distances in solutions of functionalized thiacalix[4]arenes according to NMR spectroscopic data (NOESY). Russ Chem Bull 53, 2269–2275 (2004). https://doi.org/10.1007/s11172-005-0112-z
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/s11172-005-0112-z