Diverse associations in the ternary systems of β-cyclodextrin, simple carbohydrates and phenyl derivatives of inorganic oxoacids

Zita Sebestyén, Katalin Máthé, Ágnes Buvári-Barcza, E. Vass, Ferenc Ruff, Julianna Szemán, Lajos Barcza

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Complex formation reactions of phenylboronic, phenylphosphonic, phenylarsonic and 4-aminophenyl arsonic acids with β-cyclodextrin (cycloheptaamylose, β-CD) and some simple carbohydrates (mannitol, sorbitol, glucose) have been studied using spectrophotometric, potentiometric methods and solubility measurements, supplemented with HPLC and IR analyses of the solid samples. Equilibrium constants have been determined at ionic strength of 0.2 M (NaCl) and 25 °C. β-CD forms the most stable complexes with the neutral, undissociated forms of the acids, the stability constants are as follows: phenylboronic acid: 320 ± 36, phenylphosphonic acid: 108 ± 25, phenylarsonic acid: 97 ± 4 and 4-aminophenyl arsonic acid: 107 ± 10. The stability constants for the β-CD-complexes of the ionic forms are much lower. Ternary complexes of low stability could be detected in the case of phenylphosphonic acid and sorbitol with the undissociated form and with glucose and the dianion. In more concentrated solutions phenylboronic acid forms insoluble complexes with mannitol, sorbitol and β-CD. The solid phases obtained in the ternary systems are predominantly mixtures of ester type 3:1 complexes with the carbohydrate and 1:1 inclusion complex with the β-CD. No significant interaction has been found with glucose. The phenomena can be explained by the differences in the structures of the components and by the changes in the H-bonding network of β-CD on the complex formation.

Original languageEnglish
Pages (from-to)833-838
Number of pages6
JournalCarbohydrate Research
Volume346
Issue number6
DOIs
Publication statusPublished - May 1 2011

Fingerprint

Keto Acids
Sorbitol
Cyclodextrins
Ternary systems
Carbohydrates
Mannitol
Derivatives
Glucose
Equilibrium constants
Ionic strength
Osmolar Concentration
Solubility
Esters
High Pressure Liquid Chromatography
Acids
arsonic acid
phenylphosphonic acid
benzeneboronic acid

Keywords

  • β-Cyclodextrin
  • Glucose
  • Phenylboronic acid
  • Phenylphosphonic acid
  • Sorbitol
  • Ternary complexes

ASJC Scopus subject areas

  • Biochemistry
  • Analytical Chemistry
  • Organic Chemistry

Cite this

Diverse associations in the ternary systems of β-cyclodextrin, simple carbohydrates and phenyl derivatives of inorganic oxoacids. / Sebestyén, Zita; Máthé, Katalin; Buvári-Barcza, Ágnes; Vass, E.; Ruff, Ferenc; Szemán, Julianna; Barcza, Lajos.

In: Carbohydrate Research, Vol. 346, No. 6, 01.05.2011, p. 833-838.

Research output: Contribution to journalArticle

Sebestyén, Zita ; Máthé, Katalin ; Buvári-Barcza, Ágnes ; Vass, E. ; Ruff, Ferenc ; Szemán, Julianna ; Barcza, Lajos. / Diverse associations in the ternary systems of β-cyclodextrin, simple carbohydrates and phenyl derivatives of inorganic oxoacids. In: Carbohydrate Research. 2011 ; Vol. 346, No. 6. pp. 833-838.
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AU - Ruff, Ferenc

AU - Szemán, Julianna

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