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Structure of the stereoisomers of tetrasubstituted p-t-butylcalix[4]arene containing a morpholine fragment: Data of 1D and 2D (NOESY) NMR spectroscopy

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Abstract

The structure of three isomers of 5,11,17,23-tetra-t-butyl-25,26,27,28-tetrakis[(morpholidocarbonyl) methoxy]-2,8,14,20-tetrathiacalix[4]arene in conformations of partial cone, 1,3-alternant and cone was studied by the methods of 1D and 2D (NOESY) 1H and 13C NMR spectroscopy in conjunction with computational modeling (semiempirical quantum-chemical PM3 calculations). Characteristic cross-peaks for each conformer in the two-dimensional NOESY spectra were established. It is found that unsymmetrical conformation of partial cone is more “flattened” as compared with highly symmetrical 1,3-alternant and cone conformations, while OCH2C(O)NC4H8O substituent is located in the exo-position. Theoretical modeling is found to be more consistent with the experimental data for highly symmetrical conformations.

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Authors and Affiliations

  1. Kazan State University, ul. Kremlevskaya 18, Kazan, 420008, Tatarstan, Russia

    F. Kh. Karataeva, M. V. Rezepova, A. Yu. Zhukov, I. I. Stoikov, I. S. Antipin & V. V. Klochkov

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  1. F. Kh. Karataeva
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  2. M. V. Rezepova
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  3. A. Yu. Zhukov
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  4. I. I. Stoikov
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  5. I. S. Antipin
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  6. V. V. Klochkov
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Correspondence to F. Kh. Karataeva.

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Original Russian Text © F.Kh. Karataeva, M.V. Rezepova, A.Yu. Zhukov, I.I. Stoikov, I.S. Antipin, V.V. Klochkov, 2009, published in Zhurnal Obshchei Khimii, 2009, Vol. 79, No. 3, pp. 477–485.

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Karataeva, F.K., Rezepova, M.V., Zhukov, A.Y. et al. Structure of the stereoisomers of tetrasubstituted p-t-butylcalix[4]arene containing a morpholine fragment: Data of 1D and 2D (NOESY) NMR spectroscopy. Russ J Gen Chem 79, 466–474 (2009). https://doi.org/10.1134/S1070363209030219

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  • DOI: https://doi.org/10.1134/S1070363209030219

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