Abstract.
The complexation of p-tert-butylphenyl p-tert-butylbenzoate and N-(p-tert-butylphenyl)-p-tert-butylbenzamide with a β-cyclodextrin derivative formed by two cyclodextrin units linked by a disulfide bridge on one of the C6 atoms has been studied by computational methods. The better amide solubility and the better internal interactions of the ester complex explain the experimentally observed better association constant for the ester. The free-energy perturbation methodology and molecular mechanics/Poisson–Boltzmann surface area analysis have been used to explain the problem and to compare the results.
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Received: 14 April 2002 / Accepted: 11 August 2002 / Published online: 4 November 2002
Acknowledgements. The Kollman group at the University of California San Francisco is gratefully acknowledged for support and encouragement throughout all this study. The authors thank UAB for inland and outland fellowships to I.B.. Financial support was obtained from grant no. PPQ2000-0369 from the “Ministerio de Ciencia y Tecnologia” (Spain). Intensive computations were performed either with the computers of the Kollman group or with those of CESCA-C4 (Catalonia, Spain).
Correspondence to: C. Jaime e-mail: carlos.jaime@uab.es
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Beà, I., Jaime, C. & Kollman, P. Molecular recognition by β-cyclodextrin derivatives: molecular dynamics, free-energy perturbation and molecular mechanics/ Poisson–Boltzmann surface area goals and problems. Theor Chem Acc 108, 286–292 (2002). https://doi.org/10.1007/s00214-002-0384-4
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DOI: https://doi.org/10.1007/s00214-002-0384-4