Complexation of phenols with β- and γ-cyclodextrins

Determination of the association constants by using the isomerization of spiropyran

Yoshimi Sueishi, Tamami Miyakawa

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

As a chemical indicator, the isomerization rate of so-called 6-SO3--spiropyran was used to estimate the equilibrium constants for the inclusion complex formation of β- and γ-cyclodextrins (β and γ-CDs). The association constants for inclusion complexes of β- and γ-CDs with various kinds of phenols were determined. It was found that β- and γ-CDs form 1:1 and 1:2 inclusion complexes with phenols, respectively. The substituent effects on the association constants for the 4-substituted phenols-β-CD system can be interpreted in terms of the geometry of the inclusion complex. The magnitude of the association constants for the inclusion complex is related to molecular polarizability of the guest molecule. Based on the results, the dominat factor for CD complexation with phenols is discussed.

Original languageEnglish
Pages (from-to)541-546
Number of pages6
JournalJournal of Physical Organic Chemistry
Volume12
Issue number7
Publication statusPublished - Jul 1999

Fingerprint

Phenols
Cyclodextrins
Isomerization
Complexation
phenols
isomerization
Association reactions
inclusions
chemical indicators
Equilibrium constants
spiropyran
Molecules
Geometry
estimates
geometry
molecules

Keywords

  • Cyclodextrins
  • Inclusion complex
  • Phenols
  • Spiropyran

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry

Cite this

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abstract = "As a chemical indicator, the isomerization rate of so-called 6-SO3--spiropyran was used to estimate the equilibrium constants for the inclusion complex formation of β- and γ-cyclodextrins (β and γ-CDs). The association constants for inclusion complexes of β- and γ-CDs with various kinds of phenols were determined. It was found that β- and γ-CDs form 1:1 and 1:2 inclusion complexes with phenols, respectively. The substituent effects on the association constants for the 4-substituted phenols-β-CD system can be interpreted in terms of the geometry of the inclusion complex. The magnitude of the association constants for the inclusion complex is related to molecular polarizability of the guest molecule. Based on the results, the dominat factor for CD complexation with phenols is discussed.",
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T1 - Complexation of phenols with β- and γ-cyclodextrins

T2 - Determination of the association constants by using the isomerization of spiropyran

AU - Sueishi, Yoshimi

AU - Miyakawa, Tamami

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N2 - As a chemical indicator, the isomerization rate of so-called 6-SO3--spiropyran was used to estimate the equilibrium constants for the inclusion complex formation of β- and γ-cyclodextrins (β and γ-CDs). The association constants for inclusion complexes of β- and γ-CDs with various kinds of phenols were determined. It was found that β- and γ-CDs form 1:1 and 1:2 inclusion complexes with phenols, respectively. The substituent effects on the association constants for the 4-substituted phenols-β-CD system can be interpreted in terms of the geometry of the inclusion complex. The magnitude of the association constants for the inclusion complex is related to molecular polarizability of the guest molecule. Based on the results, the dominat factor for CD complexation with phenols is discussed.

AB - As a chemical indicator, the isomerization rate of so-called 6-SO3--spiropyran was used to estimate the equilibrium constants for the inclusion complex formation of β- and γ-cyclodextrins (β and γ-CDs). The association constants for inclusion complexes of β- and γ-CDs with various kinds of phenols were determined. It was found that β- and γ-CDs form 1:1 and 1:2 inclusion complexes with phenols, respectively. The substituent effects on the association constants for the 4-substituted phenols-β-CD system can be interpreted in terms of the geometry of the inclusion complex. The magnitude of the association constants for the inclusion complex is related to molecular polarizability of the guest molecule. Based on the results, the dominat factor for CD complexation with phenols is discussed.

KW - Cyclodextrins

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KW - Spiropyran

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