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Cyclodextrin effect on solvolysis of ortho benzoyl chlorides

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Abstract

A kinetic study was carried out on the solvolysis of ortho benzoyl chlorides in the presence of α-, β- and γ-Cyclodextrin (CD). The solvolysis mechanism of benzoyl chlorides is sensitive to the substituents, and to the solvent in which the reaction takes place. In water, the behaviour exhibited by benzoyl chlorides which have electron-attracting groups, is consistent with an associative mechanism whilst electron-donating substituents induce a dissociative mechanism. The results obtained in the presence of CD show a decrease in the observed rate constant, k obs, as the CD concentration increases. This behaviour can be explained if these substrates undergo solvolysis through a dissociative path in the presence of α-, β- and γ-CD.

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Acknowledgments

This work was supported by Ministerio de Ciencia y Tecnología (Project CTQ2005-04779) and Xunta de Galiza (PGIDT03-PXIC20905PN and PGIDIT04TMT209003PR). M. M. P. thanks to Ministerio de Educación a FPU research-training grant.

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  1. Dpto. Química Física, Facultad de Química, Avda. das Ciencias s/n, Universidad de Santiago de Compostela, 15782, Santiago, Spain

    J. Báscuas, L. García-Río, J. R. Leis & M. Méndez-Pérez

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  1. J. Báscuas
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  2. L. García-Río
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  3. J. R. Leis
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  4. M. Méndez-Pérez
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Correspondence to J. Báscuas.

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Báscuas, J., García-Río, L., Leis, J.R. et al. Cyclodextrin effect on solvolysis of ortho benzoyl chlorides. J Incl Phenom Macrocycl Chem 57, 603–606 (2007). https://doi.org/10.1007/s10847-006-9276-x

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  • DOI: https://doi.org/10.1007/s10847-006-9276-x

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