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Characterization of Aqueous and Solid Inclusion Complexes of Diuron and Isoproturon with β-Cyclodextrin

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Abstract:

The interaction of diuron and isoproturon herbicides with β-cyclodextrin is conducive to the formation of inclusion compounds in aqueous solution as well as in the solid state. The physico-chemical study of these complexes was carried out by various analytical techniques such as ultraviolet (UV), Fourier transform infrared (FT-IR), Raman, X-ray diffraction, and 1H-NMR (nuclear magnetic resonance) spectroscopies. The existence of inclusion complexes in water solution between the β-cyclodextrin and each of the herbicides was revealed by electronic absorption and 1H-NMR spectroscopies. A 1:1 stoichiometry was determined for both complexes in aqueous medium from UV absorption spectra by using the Benesi–Hildebrand method; the relative stability constants at room temperature were calculated at 2700 ± 300 L mol-1 and 750 ± 50 L mol-1 for isoproturon and diuron, respectively. In the solid state, inclusion processes with β-cyclodextrin were characterized by means of infrared and Raman techniques and confirmed by X-ray diffraction spectra.

Keywords: 1H-NMR; Diuron; FT-IR; Raman; Fourier transform infrared spectroscopy; Herbicides; Isoproturon; Nuclear magnetic resonance; UV absorption; X-ray diffraction

Document Type: Research Article

DOI: http://dx.doi.org/10.1366/000370204872999

Affiliations: 1: Laboratoire de Spectrochimie Infrarouge et Raman, UMR CNRS 8516, Centre d'Etudes et de Recherches Lasers et Applications, Bât. C5, Université; des Sciences et Technologies de Lille, 59655 Villeneuve d'Ascq Cedex, France 2: Service Commun de RMN, Bât. C4, Universite´ des Sciences et Technologies de Lille, 59655 Villeneuve d'Ascq Cedex, France 3: Laboratoire Syste`mes Chimiques Complexes, UMR CNRS 6171, Université desSciences et Techniques de St Jérôme, Avenue Escadrille Normandie-Niemen, 13397 Marseille Cedex 20, France

Publication date: June 1, 2004

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