Differential effects of substituent and pressure on induced inclusion complexation of 6-O-α-D-glucosyl-β-cyclodextrin with 4-substituted phenols

Yoshimi Sueishi, Naoya Inazumi, Tatsuhiro Ide, Tadashi Hanaya

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

The inclusion complexation of 6-O-α-D-glucosyl-β-cyclodextrin (G-β-CD), in which the glucosyl side chain is introduced to β-CD, with various kinds of phenols was studied spectrophotometrically at high pressures. The characteristic effects of substituent and pressure were found for the inclusion complexation of G-β-CD. The association constants K for the G-β-CD inclusion complexation increased with an increase in the bulkiness of the 4-substituent groups in phenols. As the external pressure increases, the inclusion constants for the G-β-CD complexation increased and the reaction volumes were estimated to be -3.8 to -19.4 cm3 mol-1 from their pressure dependences. From analysis of the effect of pressure on the inclusion complexation with G-β-CD, the number of water molecules included in the G-β-CD cavity in water was estimated. The number of water molecules repelled from the CD cavity plays an important role in the change in volume upon inclusion. In addition, the structures of the inclusion complexes of G-β-CD with phenols have been established by 1D and 2D NMR measurements. Based on the results, we suggested that the ability of the G-β-CD inclusion complexation is enhanced by the interaction between guest molecules and the glucosyl side chain of G-β-CD.

Original languageEnglish
Pages (from-to)201-208
Number of pages8
JournalJournal of Inclusion Phenomena and Macrocyclic Chemistry
Volume54
Issue number3-4
DOIs
Publication statusPublished - Apr 2006

Fingerprint

cyclodextrins
Phenols
Cyclodextrins
Complexation
phenols
inclusions
Pressure
Molecules
Water
water
molecules
cavities
pressure dependence
Nuclear magnetic resonance
Association reactions
nuclear magnetic resonance

Keywords

  • Glucosyl-β-cyclodextrin
  • Inclusion complex
  • NMR study
  • Phenols
  • Pressure effect

ASJC Scopus subject areas

  • Chemistry(all)
  • Condensed Matter Physics

Cite this

@article{ea41f68d2f2b43789fcbebce7a56a68a,
title = "Differential effects of substituent and pressure on induced inclusion complexation of 6-O-α-D-glucosyl-β-cyclodextrin with 4-substituted phenols",
abstract = "The inclusion complexation of 6-O-α-D-glucosyl-β-cyclodextrin (G-β-CD), in which the glucosyl side chain is introduced to β-CD, with various kinds of phenols was studied spectrophotometrically at high pressures. The characteristic effects of substituent and pressure were found for the inclusion complexation of G-β-CD. The association constants K for the G-β-CD inclusion complexation increased with an increase in the bulkiness of the 4-substituent groups in phenols. As the external pressure increases, the inclusion constants for the G-β-CD complexation increased and the reaction volumes were estimated to be -3.8 to -19.4 cm3 mol-1 from their pressure dependences. From analysis of the effect of pressure on the inclusion complexation with G-β-CD, the number of water molecules included in the G-β-CD cavity in water was estimated. The number of water molecules repelled from the CD cavity plays an important role in the change in volume upon inclusion. In addition, the structures of the inclusion complexes of G-β-CD with phenols have been established by 1D and 2D NMR measurements. Based on the results, we suggested that the ability of the G-β-CD inclusion complexation is enhanced by the interaction between guest molecules and the glucosyl side chain of G-β-CD.",
keywords = "Glucosyl-β-cyclodextrin, Inclusion complex, NMR study, Phenols, Pressure effect",
author = "Yoshimi Sueishi and Naoya Inazumi and Tatsuhiro Ide and Tadashi Hanaya",
year = "2006",
month = "4",
doi = "10.1007/s10847-005-7368-7",
language = "English",
volume = "54",
pages = "201--208",
journal = "Journal of Inclusion Phenomena and Macrocyclic Chemistry",
issn = "1388-3127",
publisher = "Kluwer Academic Publishers",
number = "3-4",

}

TY - JOUR

T1 - Differential effects of substituent and pressure on induced inclusion complexation of 6-O-α-D-glucosyl-β-cyclodextrin with 4-substituted phenols

AU - Sueishi, Yoshimi

AU - Inazumi, Naoya

AU - Ide, Tatsuhiro

AU - Hanaya, Tadashi

PY - 2006/4

Y1 - 2006/4

N2 - The inclusion complexation of 6-O-α-D-glucosyl-β-cyclodextrin (G-β-CD), in which the glucosyl side chain is introduced to β-CD, with various kinds of phenols was studied spectrophotometrically at high pressures. The characteristic effects of substituent and pressure were found for the inclusion complexation of G-β-CD. The association constants K for the G-β-CD inclusion complexation increased with an increase in the bulkiness of the 4-substituent groups in phenols. As the external pressure increases, the inclusion constants for the G-β-CD complexation increased and the reaction volumes were estimated to be -3.8 to -19.4 cm3 mol-1 from their pressure dependences. From analysis of the effect of pressure on the inclusion complexation with G-β-CD, the number of water molecules included in the G-β-CD cavity in water was estimated. The number of water molecules repelled from the CD cavity plays an important role in the change in volume upon inclusion. In addition, the structures of the inclusion complexes of G-β-CD with phenols have been established by 1D and 2D NMR measurements. Based on the results, we suggested that the ability of the G-β-CD inclusion complexation is enhanced by the interaction between guest molecules and the glucosyl side chain of G-β-CD.

AB - The inclusion complexation of 6-O-α-D-glucosyl-β-cyclodextrin (G-β-CD), in which the glucosyl side chain is introduced to β-CD, with various kinds of phenols was studied spectrophotometrically at high pressures. The characteristic effects of substituent and pressure were found for the inclusion complexation of G-β-CD. The association constants K for the G-β-CD inclusion complexation increased with an increase in the bulkiness of the 4-substituent groups in phenols. As the external pressure increases, the inclusion constants for the G-β-CD complexation increased and the reaction volumes were estimated to be -3.8 to -19.4 cm3 mol-1 from their pressure dependences. From analysis of the effect of pressure on the inclusion complexation with G-β-CD, the number of water molecules included in the G-β-CD cavity in water was estimated. The number of water molecules repelled from the CD cavity plays an important role in the change in volume upon inclusion. In addition, the structures of the inclusion complexes of G-β-CD with phenols have been established by 1D and 2D NMR measurements. Based on the results, we suggested that the ability of the G-β-CD inclusion complexation is enhanced by the interaction between guest molecules and the glucosyl side chain of G-β-CD.

KW - Glucosyl-β-cyclodextrin

KW - Inclusion complex

KW - NMR study

KW - Phenols

KW - Pressure effect

UR - http://www.scopus.com/inward/record.url?scp=33646468793&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33646468793&partnerID=8YFLogxK

U2 - 10.1007/s10847-005-7368-7

DO - 10.1007/s10847-005-7368-7

M3 - Article

AN - SCOPUS:33646468793

VL - 54

SP - 201

EP - 208

JO - Journal of Inclusion Phenomena and Macrocyclic Chemistry

JF - Journal of Inclusion Phenomena and Macrocyclic Chemistry

SN - 1388-3127

IS - 3-4

ER -