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NMR studies of complex formation between natural cyclodextrins and benzene

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Abstract

Inclusion complexes of benzene (Bz) with cyclodextrins (CD) have been investigated so far using non-NMR techniques in various solvents resulting in conflicting data. Here, the first application of NMR spectroscopy in combination with rigorous statistical analysis of the results has allowed us to determine accurately the stoichiometry of complexes and their association constants. Titration measurements have been performed by 1H NMR spectroscopy in D2O at a magnetic field B0 of 14.1 T. αCD and γCD host molecules form weak 1 : 1 complexes with Bz. In contrast, Bz and βCD build 1 : 1 and 2 : 1 complexes coexisting in solution with large binding constants. Binding of second benzene molecule is strongly cooperative.

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Author notes

  1. Jacek Wójcik guest scientist.

Authors and Affiliations

  1. Faculty of Chemistry, Biological and Chemical Research Centre, University of Warsaw, Żwirki i Wigury 101, Warszawa, 02-089, Poland

    Gabriela Szczupaj, Jacek Wójcik & Michał Nowakowski

  2. Institute of Biochemistry and Biophysics, Polish Academy of Sciences, Pawińskiego 5A, Warszawa, 02- 106, Poland

    Andrzej Ejchart

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  1. Gabriela Szczupaj
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  2. Jacek Wójcik
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  3. Andrzej Ejchart
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  4. Michał Nowakowski
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Contributions

AE and MN: conceptualization; GS, MN and JW: samples preparation; GS and MN: measurements; GS and AE: data analysis; GS, JW, AE and MN: manuscript preparations.

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Correspondence to Michał Nowakowski.

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Szczupaj, G., Wójcik, J., Ejchart, A. et al. NMR studies of complex formation between natural cyclodextrins and benzene. J Incl Phenom Macrocycl Chem 104, 129–136 (2024). https://doi.org/10.1007/s10847-024-01222-8

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