Abstract
Dinitroxyl crown ether biradical, 4,13-bis[2-hydroxy-3-(2,2,4,4-tetramethyl-3-oxylo1,2,3,4-tetrahydro-γ-carbol-9-yl)propyl]-1,7,10,16-tetraoxa-4,13-diazacyclooctadecane, was synthesized and studied by X-ray structural analysis and ESR spectroscopy. The ESR spectra in aqueous and aqueous-alcoholic solutions show a triplet withaN = 1.65±0.05 mT. This triplet is retained in the presence of Na+, K+, and Mg2+ ions. On addition of Ca2+ ions, the triplet is transformed into the quintet because of the change in the conformation of the crown ether biradical and decrease in the distance between the nitroxyl groups. The new crown ether biradicdl containing hydrophobic indole groups may be used for studying the mechanism of Ca2+ ion transport in biomembranes by ESR spectroscopy.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
A. B. Shapiro, I. I. Lobysheva, V. I. Suskina, and M. G. Gol'dfel'd,DokL Akad. Nauk, 1993,330, 223 [Dokl. Chem., 1993,330 (Engl. Transl.)].
V. A. Reznikov, T. A. Berezina, L. B. Volodarskii, and E. G. Lubenets,Izv. Akad. Nauk, Ser. Khim., 1993, 1770 [Russ. Chem. Bull., 1993,42, 1694 (Engl. Transl.)].
M. P. Eastman, D. E. Patterson, R. A. Bartsch, Y. Lin, and P. G. Eller,J. Phys. Chem., 1982,86, 2052.
K. J. ishizu, H. Kohama, and K. Mukai,Chem. Lett., 1978, 227.
H. Dugas and M. Ptak,J. Chem. Soc., Chem. Commun., 1982, T10.
J. F. W. Keana, J. Cuomo, L. Lex, and S. E. Seyedrezai,J. Org. Chem., 1983,48, 2647.
E. G. Rozanlsev and A. B. Shapiro,Izv. Akad. Nauk SSSR, Ser. Khim., 1964, 1123 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 196413, 1043 (Engl. Transl.)].
A. B. Shapiro, B. V. Rozynov, E. G. Rozantsev, N. F. Kucherova, L. A. Aksanova, and N. N. Novikova, Izv, Akad. Nauk SSSR, Ser. Khim., 1971, 86T [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1971, 20, 784 (Engl. Transl.)].
A. N. Kuznetsov, V. Ebert, G. Lassman, and A. B. Shapiro,Biochim. Biophys. Acta, 1975,379, 139.
F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, and R. Taylor,J. Chem. Soc., Perkin Trans. 2, 1987, 1.
I. I. Lobysheva and A. B. Shapiro, Arstrs., Int. Conf. on Bioradicals Detected by ESR Spectroscopy, Yamagata, Japan, 1994, 39.
W. Robinson and G. M. Sheldrick,SHELX, inCrystallographic Computing-Techniques and New Technologies, Eds. N. W. Isaacs and M. R. Taylor, Oxford Univ. Press, Oxford, England, 1988, 366.
Author information
Authors and Affiliations
Additional information
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 920–924, April, 1996.
Rights and permissions
About this article
Cite this article
Shapiro, A.B., Suskina, V.I., Khrustatev, V.N. et al. Synthesis and crystal structure of dinitroxyl crown ether biradical with indole groups in the side chains. Russ Chem Bull 45, 875–879 (1996). https://doi.org/10.1007/BF01431316
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/BF01431316