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Influence of the Configuration of an Asymmetric Carbon Center on the Parameters of the Nuclear Magnetic Resonance Spectra of Inherently Chiral N-(1-Phenylethyl)Amides of Calix[4]Arene Acetic Acids: Determination of the Absolute Stereochemical Configuration of the Macrocycle

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Theoretical and Experimental Chemistry Aims and scope

Comparison of the XRD data and NMR spectra of S or R forms of N-(1-phenylethyl)amides of calix[4]arene acetic acids shows that the chiral N-(1-phenylethyl)aminocarbonylmethyl group can be used for determination of the absolute configuration of inherently chiral calixarene macrocycles by Mosher’s method. Rules for such determination are formulated.

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Acknowledgement

The work was partially supported by the National Academy of Sciences of Ukraine (grant No. 0118U006190, target program “New generation smart sensors based on modern materials and technologies”).

The authors express gratitude to O. I. Kolodyazhnyi who drew their attention to this determination method of calixarene stereoisomer configurations. The authors also express gratitude to S. V. Shyshkina for assisting in obtaining X-ray structural data.

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Authors and Affiliations

  1. Institute of Organic Chemistry, NAS of Ukraine, Kyiv, Ukraine

    O. A. Yesypenko, O. O. Trybrat, O. O. Vashchenko & S. Yu. Suikov

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  1. O. A. Yesypenko
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  2. O. O. Trybrat
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  3. O. O. Vashchenko
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  4. S. Yu. Suikov
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Correspondence to O. A. Yesypenko.

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Translated from Teoretychna ta Eksperymentalna Khimiya, Vol. 58, No. 1, pp. 48-54, January-February, 2022.

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Yesypenko, O.A., Trybrat, O.O., Vashchenko, O.O. et al. Influence of the Configuration of an Asymmetric Carbon Center on the Parameters of the Nuclear Magnetic Resonance Spectra of Inherently Chiral N-(1-Phenylethyl)Amides of Calix[4]Arene Acetic Acids: Determination of the Absolute Stereochemical Configuration of the Macrocycle. Theor Exp Chem 58, 54–60 (2022). https://doi.org/10.1007/s11237-022-09722-9

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  • DOI: https://doi.org/10.1007/s11237-022-09722-9

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