"On the complexation of allopurinol with β-cyclodextrin"

Verónica Jiménez, Joel B. Alderete, Eduardo J. Delgado, Julio Belmar, José Gavín

Resultado de la investigación: Article

3 Citas (Scopus)

Resumen

NMR diffusion coefficient measurements and PM3 theoretical calculations were employed in the study of the inclusion complexation of allopurinol with β-cyclodextrin (β-CD) at pH 6.5 and 10.0. Experimental findings revealed an increase in the association constant from 16 to 30 M-1 as a consequence of guest deprotonation. PM3 quantum-mechanical calculations were performed to investigate the complexation process between β-CD and allopurinol, considering the most stable neutral and anionic tautomers of the guest. The binding energies obtained from the computational study were in agreement with the experimental observations, indicating that the anionic complex was more stable than the neutral one. Such unusual behavior was related to hydrogen bonding interactions between β-CD and the anionic guest, leading to the increase of the association constant as a consequence of guest deprotonation.

Idioma originalEnglish
Páginas (desde-hasta)217-223
Número de páginas7
PublicaciónStructural Chemistry
Volumen17
N.º2
DOI
EstadoPublished - 1 mar 2006

Huella dactilar

Deprotonation
Allopurinol
Cyclodextrins
Complexation
Association reactions
tautomers
Binding energy
Hydrogen bonds
diffusion coefficient
binding energy
Nuclear magnetic resonance
inclusions
nuclear magnetic resonance
hydrogen
interactions

ASJC Scopus subject areas

  • Condensed Matter Physics
  • Physical and Theoretical Chemistry

Citar esto

Jiménez, V., Alderete, J. B., Delgado, E. J., Belmar, J., & Gavín, J. (2006). "On the complexation of allopurinol with β-cyclodextrin". Structural Chemistry, 17(2), 217-223. https://doi.org/10.1007/s11224-006-9002-8
Jiménez, Verónica ; Alderete, Joel B. ; Delgado, Eduardo J. ; Belmar, Julio ; Gavín, José. / "On the complexation of allopurinol with β-cyclodextrin". En: Structural Chemistry. 2006 ; Vol. 17, N.º 2. pp. 217-223.
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Jiménez, V, Alderete, JB, Delgado, EJ, Belmar, J & Gavín, J 2006, '"On the complexation of allopurinol with β-cyclodextrin"', Structural Chemistry, vol. 17, n.º 2, pp. 217-223. https://doi.org/10.1007/s11224-006-9002-8

"On the complexation of allopurinol with β-cyclodextrin". / Jiménez, Verónica; Alderete, Joel B.; Delgado, Eduardo J.; Belmar, Julio; Gavín, José.

En: Structural Chemistry, Vol. 17, N.º 2, 01.03.2006, p. 217-223.

Resultado de la investigación: Article

TY - JOUR

T1 - "On the complexation of allopurinol with β-cyclodextrin"

AU - Jiménez, Verónica

AU - Alderete, Joel B.

AU - Delgado, Eduardo J.

AU - Belmar, Julio

AU - Gavín, José

PY - 2006/3/1

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AB - NMR diffusion coefficient measurements and PM3 theoretical calculations were employed in the study of the inclusion complexation of allopurinol with β-cyclodextrin (β-CD) at pH 6.5 and 10.0. Experimental findings revealed an increase in the association constant from 16 to 30 M-1 as a consequence of guest deprotonation. PM3 quantum-mechanical calculations were performed to investigate the complexation process between β-CD and allopurinol, considering the most stable neutral and anionic tautomers of the guest. The binding energies obtained from the computational study were in agreement with the experimental observations, indicating that the anionic complex was more stable than the neutral one. Such unusual behavior was related to hydrogen bonding interactions between β-CD and the anionic guest, leading to the increase of the association constant as a consequence of guest deprotonation.

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KW - NMR-diffusion

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