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Understanding non-covalent interactions by NMR in urea- and thiourea-substituted calixarene complexes

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Abstract

High level quantum mechemical gauge-independent atomic orbital (GIAO)-DFT NMR calculations (B3LYP/6-311++G**) were performed to address the binding interactions of functionalized thiourea and urea substituted calixarenes. 1H NMR chemical shifts were evaluated for hydrogen-bonded protons of calixarenes (1,2) and their anionic-complexes with F−, Cl−, CN−, N3− and SCN−. Comparison of experimental vs. calculated anion binding geometries along with their chemical shift were made to decipher the structural features. The calculated chemical shift exhibit reasonable agreement with the experimental data. We showed that the substitution of C=O to C=S in calixarenes significantly affect the interaction with anions. In particular, urea substituted calixarenes-F− possess most deshielded hydrogens among the modeled inclusion complexes. Our study showed that NMR calculation in combination with calixarene structural models can be helpful in characterizing the non-covalent interactions.

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Acknowledgements

This work was supported by the Department of Science & Technology (DST), New Delhi under INSPIRE-SRF to Mohd Athar. H.Behzadi and S.Makki thanks Kharazmi University for financial support.

Funding

Funding was provided by Department of Science and Technology, Ministry of Science and Technology (Grant no. 150167) under Inspire Fellowship scheme to Mohd Athar.

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Authors and Affiliations

  1. CCG@CUG, School of Chemical Science, Central University of Gujarat, Gandhinagar, Gujarat, 382030, India

    Mohd Athar

  2. Department of Physical Chemistry, Faculty of Chemistry, Kharazmi University, Tehran, Iran

    Hadi Behzadi & Samane Makki

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  1. Mohd Athar
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  2. Hadi Behzadi
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  3. Samane Makki
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Correspondence to Hadi Behzadi.

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Athar, M., Behzadi, H. & Makki, S. Understanding non-covalent interactions by NMR in urea- and thiourea-substituted calixarene complexes. Monatsh Chem 151, 743–749 (2020). https://doi.org/10.1007/s00706-020-02603-8

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  • DOI: https://doi.org/10.1007/s00706-020-02603-8

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