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Open Chemistry

formerly Central European Journal of Chemistry

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Volume 9, Issue 6

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Complexation of [2.2]paracyclophane with β- and γ-cyclodextrins studied by HPLC and NMR

Helena Dodziuk / Anna Bielejewska / Wojciech Schilf / Haruhisa Ueda
Published Online: 2011-09-27 | DOI: https://doi.org/10.2478/s11532-011-0095-6

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Abstract

The NMR spectra of [2.2]paracyclophane with β- or γ-cyclodextrin in DMF-d7 at room temperature do not show significant complexation, while HPLC of the complexes in mixed H2O:alcohol solvents demonstrate complexation with different stoichiometries. At 243 K in DMF solution the H3 and H5 NMR signals of γ-cyclodextrin (but not β) exhibit complexation-induced chemical shifts denoting complex formation. According to HPLC, at room temperature the [2.2]paracyclophane complex with β-cyclodextrin in 20% H2O:EtOH exhibits 1:2 stoichiometry with K 1 = 1×102 ± 2, K 2 = 9.0×104 ± 2×103 (K = 9×106) while that with γ-cyclodextrin in 50% H2O:MeOH exhibits 1:1 stoichiometry with K 1 = 4×103 ± 150 M−1. Thermodynamic parameters for both complexes have been estimated from the retention time temperature dependence. For the β-cyclodextrin complexation at 25°C ΔG 0CD is −39.7 kJ mol−1 while ΔH 0CD and ΔS 0CD are −88.2 kJ mol−1 and −0.16 kJ mol−1 K−1. For γ-cyclodextrin, the corresponding values are ΔG 0CD = −20.5 kJ mol−1, ΔH 0CD = −33.5 kJ mol−1 and ΔS 0CD = −0.04 kJ mol−1 K−1.

Keywords: Cyclodextrin cyclophane complexes; HPLC; NMR; Thermodynamic parameters

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About the article

Published Online: 2011-09-27

Published in Print: 2011-12-01

Citation Information: Open Chemistry, Volume 9, Issue 6, Pages 1056–1061, ISSN (Online) 2391-5420, DOI: https://doi.org/10.2478/s11532-011-0095-6.

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© 2011 Versita Warsaw. This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License. BY-NC-ND 3.0

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