Abstract
Steady-state, time-resolved fluorescence and Molecular Mechanics techniques have been used to study the complexation of 1-methyl naphthalenecarboxylate with three naturally occurring cyclodextrins (CDs). Emission spectra of 1MN show two overlapping electronic bands. The stoichiometry, the formation constants of the complexes and the thermodynamics parameters upon inclusion were obtained from the change of intensity ratios R of the maxima of both bands and 〈τ〉 with [CD] and temperature. As with the 2-methyl naphthalenecarboxylate (2MN) guest, 1:1 stoichiometries were obtained for all complexes. The formation constants, however, were relatively low compared to those obtained for 2MN. Geometry of the complexes from Molecular Mechanics in the presence of water agrees with the experimental stoichiometry of the complexes and the signs of enthalpy and entropy changes. Quenching, R at [CD]→∞ and fluorescence depolarization measurements also support the proposed structures. As with 2MN the inclusion is mostly dominated by van der Waals interactions.
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Acknowledgements
This research was supported by Comunidad de Madrid (CAM projects: GR/MAT/0810/2004; S-055/MAT/0227), CICYT (project CTQ2005-04710/BQU) and Universidad de Alcalá (grant to A.D.M.). We wish to express our thanks to M.L. Heijnen for assistance with the preparation of the manuscript.
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Marino, A.D., Rubio, L. & Mendicuti, F. Fluorescence and Molecular Mechanics of 1-Methyl Naphthalenecarboxylate/Cyclodextrin Complexes in Aqueous Medium. J Incl Phenom Macrocycl Chem 58, 103–114 (2007). https://doi.org/10.1007/s10847-006-9129-7
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DOI: https://doi.org/10.1007/s10847-006-9129-7