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Permethylated β-cyclodextrin/pesticide complexes: X-ray structures and thermogravimetric assessment of kinetic parameters for complex dissociation

Journal of Inclusion Phenomena and Macrocyclic Chemistry volume 75, pages 47–56 (2013)Cite this article

Abstract

The X-ray crystal structures of the inclusion complexes formed between three pesticides (two organophosphorus insecticides and one chloroacetanilide herbicide) and permethylated β-cyclodextrin (TRIMEB) are reported. The complexes TRIMEB–fenitrothion (1), TRIMEB–fenthion (2) and TRIMEB–acetochlor (3) are members of a commonly occurring isostructural series. The mode of inclusion of the two organophosphate insecticides is very similar, while the acetochlor molecule, which is structurally quite distinct from the two insecticide molecules, adopts a somewhat different position within the TRIMEB cavity. In addition to the structural elucidation of these complexes, their thermal behaviour was investigated using isothermal and non-isothermal thermogravimetry. The isothermal results showed that the dissociation of the guest molecules from the TRIMEB cavities can best be described by two mechanisms, namely a first-order reaction model and a three-dimensional diffusion model. Both the isothermal and non-isothermal methods allowed the determination of the activation energies of the guest loss process for each complex.

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Acknowledgments

This material is based on research supported by the National Research Foundation (NRF) under Grant number 67381. MRC and DLC express their thanks to the NRF and the University of Cape Town for financial assistance. Financial assistance from Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET), Fondo para la Investigaciόn Científica y Tecnolόgica (FONCYT), Ministerio de Ciencia y Tecnología (MINCyT), Córdoba (Argentina) and support from the National University of Córdoba are greatly acknowledged. This work was carried out as part of a bilateral cooperation project supported by the NRF (South Africa) and MINCyT (Argentina). NMR is a grateful recipient of a fellowship from CONICET (Argentina).

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Authors and Affiliations

  1. Department of Chemistry, University of Cape Town, Rondebosch, 7701, South Africa

    Dyanne L. Cruickshank, Vaughan J. Maurel, Susan A. Bourne & Mino R. Caira

  2. Instituto de Investigaciones en Físico Química de Córdoba (INFIQC), Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, X5000HUA, Córdoba, Argentina

    Natalia M. Rougier, Rita H. de Rossi & Elba I. Buján

Authors
  1. Dyanne L. Cruickshank
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  2. Natalia M. Rougier
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  3. Vaughan J. Maurel
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  4. Rita H. de Rossi
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  5. Elba I. Buján
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  6. Susan A. Bourne
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  7. Mino R. Caira
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Correspondence to Mino R. Caira.

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Cruickshank, D.L., Rougier, N.M., Maurel, V.J. et al. Permethylated β-cyclodextrin/pesticide complexes: X-ray structures and thermogravimetric assessment of kinetic parameters for complex dissociation. J Incl Phenom Macrocycl Chem 75, 47–56 (2013). https://doi.org/10.1007/s10847-012-0145-5

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  • DOI: https://doi.org/10.1007/s10847-012-0145-5

Keywords

  • Pesticides
  • Inclusion complexes
  • Permethylated β-cyclodextrin
  • Single crystal X-ray diffraction
  • Thermal decomposition kinetics