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Inclusion complexes of some thiourea derivatives in cyclodextrins

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Abstract

The formation of the inclusion complexes of five thioureea derivatives both with α- and β-cyclodextrins is studied. The most stable conformers of these thioureea derivatives are selected. The deformation, binding and stabilization energies are evaluated by DFT calculations considering the dispersion corrections at the level D3. Basis set superposition errors were computed by counterpoise procedure. It is proved that a thioureea derivative can be inserted both in the cavity of a single cyclodextrin and of a cyclodextrin dimer, forming in both cases a soluble supramolecular structure. In the latter case the stability of the inclusion complex is mainly due to interaction between the two cyclodextrins. The formation of a supramolecular structure composed by one thioureea derivative and two cyclodextrins is possible by the insertion of a thioureea derivative in a cyclodextrin dimer as well as by the addition of a second cyclodextrin to an inclusion complex formed by one thioureea derivative and one cyclodextrin.

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Acknowledgements

This paper was partly done within the research program “Chemical Thermodynamics and Kinetics. Quantum chemistry” of the “Ilie Murgulescu” Institute of Physical Chemistry, financed by the Romanian Academy. The authors gratefully acknowledge the computing time granted by the Institute of Physical Chemistry “Ilie Murgulescu” on the HPC-ICF infrastructure that was developed in the frame of the Capacities Project 84 CpI/13.09.2007—National Authority for Scientific Research, Bucharest, Romania. We thank to Dr. Viorel Chihaia for his critical remarks.

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  1. “Ilie Murgulescu” Institute of Physical Chemistry, Romanian Academy, 202 Splaiul Independentei St., 060021, Bucharest, Romania

    C. S. Stoicescu, A. D. Neacşu & G. Munteanu

  2. Pharmaceutical Chemistry Department, “Carol Davila” University of Medicine and Pharmacy, 6 Traian Vuia St., 020956, Bucharest, Romania

    C. D. Bădiceanu

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  1. C. S. Stoicescu
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Stoicescu, C.S., Neacşu, A.D., Bădiceanu, C.D. et al. Inclusion complexes of some thiourea derivatives in cyclodextrins. J Incl Phenom Macrocycl Chem 96, 275–283 (2020). https://doi.org/10.1007/s10847-019-00968-w

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