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Study of the conformation and hydrogen bonds of the p-tetrasulfonatothiacalix[4]arene pentasodium salt by vibrational spectroscopy and DFT

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Abstract

The vibrational spectra of the p-tetrasulfonatothiacalix[4]arene pentasodium salt (TCAS) and tert-butylthiacalix[4]arene (BuTCA) were studied. Comparison of the TCAS and BuTCA IR spectra allows us to isolate the bands of tert-butyl and sulfonate groups. Geometry, IR and Raman spectra were calculated for conformation cone, partial cone, 1,2-, and 1,3-alternate. The most stable conformation of the TCAS is the cone. Characteristic bands were determined for each of the possible conformations. In the case of the TCAS molecule, four ions of sodium are coordinated with the oxygen atoms of sulfonate groups, and the fifth ion interacts with the oxygen and sulfur atoms of the macrocycle. Under the influence of sodium ions, the distribution of electron density in the TCAS molecule and its ability to supramolecular interactions change.

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Acknowledgements

The authors are grateful to the Assigned Spectral-Analytical Center of FRC Kazan Scientific Center of RAS for technical assistance in research.

Funding

Contributions to research were funded by the state assignment to Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences (AAAA-A18-118041760011–2).

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Authors and Affiliations

  1. Kazan State Architect and Civil Engineering University, 1 Zelenaya, 420043, Kazan, Russia

    Victor L. Furer

  2. A.E. Arbuzov Institute of Organic and Physical Chemistry, RAS, 8 Arbuzov Str., 420088, Kazan, Russia

    Alexandr E. Vandyukov, Sofya R. Kleshnina & Valery I. Kovalenko

  3. Kazan Federal University, Kremlyovskaya Str., 420008, Kazan, Russia

    Svetlana E. Solovieva & Igor S. Antipin

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  1. Victor L. Furer
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  2. Alexandr E. Vandyukov
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  3. Sofya R. Kleshnina
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  4. Svetlana E. Solovieva
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  5. Igor S. Antipin
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  6. Valery I. Kovalenko
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Contributions

Victor Furer: conceptualization, methodology, software, writing—original draft preparation, and editing

Alexandr Vandyukov: investigation of IR and Raman spectra

Sophia Kleshnina: synthesis of calixarenes

Svetlana Solovieva: conceptualization, methodology, reviewing, and editing

Igor Antipin: conceptualization, methodology, reviewing, and editing

Valery Kovalenko: conceptualization, methodology, reviewing, and editing

Corresponding author

Correspondence to Victor L. Furer.

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Furer, V.L., Vandyukov, A.E., Kleshnina, S.R. et al. Study of the conformation and hydrogen bonds of the p-tetrasulfonatothiacalix[4]arene pentasodium salt by vibrational spectroscopy and DFT. J Mol Model 27, 326 (2021). https://doi.org/10.1007/s00894-021-04905-y

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