NMR spectroscopic characterization of inclusion complexes of hydroxy-substituted naphthalenes with native and modified β-cyclodextrins

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Abstract

The equilibrium constants (K) for the inclusion complexation of three kinds of β-cyclodextrins (β-CDs: native β-CD, heptakis(2,6-di-O- methyl)-β-CD, and 6-O-α-d-glucosyl-β-CD) with OH-substituted naphthalenes (2-naphthol, 2,3-dihydroxynaphthalene, and 2,6- dihydroxynaphthalene) were determined from the induced chemical shifts of NMR measurements for inclusion complexes: K = 188-1,250 mol-1 dm 3. The modified β-CDs form stable 1:1 inclusion complexes with OH-substituted naphthalenes, and the high stability of inclusion complexes of 2,6-dihydroxynaphthalene having a hydrophobic body and hydrophilic ends is shown. In addition, the structures of inclusion complexes were characterized by 2D ROESY NMR measurements. The differences in the structure of the inclusion complexes were observed for three kinds of naphthol guest molecules. Based on the results, the inclusion abilities enhanced by methylation of the OH groups at the CD rim or the side chain of branched β-CD are discussed.

Original languageEnglish
Pages (from-to)135-141
Number of pages7
JournalJournal of Inclusion Phenomena and Macrocyclic Chemistry
Volume64
Issue number1-2
DOIs
Publication statusPublished - Jun 2009

Fingerprint

Naphthalenes
naphthalenes
cyclodextrins
Cyclodextrins
naphthalene
Nuclear magnetic resonance
inclusions
naphthols
Naphthols
nuclear magnetic resonance
methylation
Methylation
Equilibrium constants
Chemical shift
2,6-dihydroxynaphthalene
hydroxide ion
rims
Complexation
chemical equilibrium
Molecules

Keywords

  • Cyclodextrin
  • Inclusion complex
  • Naphthols
  • NMR
  • ROESY

ASJC Scopus subject areas

  • Condensed Matter Physics
  • Food Science
  • Chemistry(all)

Cite this

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title = "NMR spectroscopic characterization of inclusion complexes of hydroxy-substituted naphthalenes with native and modified β-cyclodextrins",
abstract = "The equilibrium constants (K) for the inclusion complexation of three kinds of β-cyclodextrins (β-CDs: native β-CD, heptakis(2,6-di-O- methyl)-β-CD, and 6-O-α-d-glucosyl-β-CD) with OH-substituted naphthalenes (2-naphthol, 2,3-dihydroxynaphthalene, and 2,6- dihydroxynaphthalene) were determined from the induced chemical shifts of NMR measurements for inclusion complexes: K = 188-1,250 mol-1 dm 3. The modified β-CDs form stable 1:1 inclusion complexes with OH-substituted naphthalenes, and the high stability of inclusion complexes of 2,6-dihydroxynaphthalene having a hydrophobic body and hydrophilic ends is shown. In addition, the structures of inclusion complexes were characterized by 2D ROESY NMR measurements. The differences in the structure of the inclusion complexes were observed for three kinds of naphthol guest molecules. Based on the results, the inclusion abilities enhanced by methylation of the OH groups at the CD rim or the side chain of branched β-CD are discussed.",
keywords = "Cyclodextrin, Inclusion complex, Naphthols, NMR, ROESY",
author = "Yoshimi Sueishi and Naoya Inazumi and Tadashi Hanaya",
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T1 - NMR spectroscopic characterization of inclusion complexes of hydroxy-substituted naphthalenes with native and modified β-cyclodextrins

AU - Sueishi, Yoshimi

AU - Inazumi, Naoya

AU - Hanaya, Tadashi

PY - 2009/6

Y1 - 2009/6

N2 - The equilibrium constants (K) for the inclusion complexation of three kinds of β-cyclodextrins (β-CDs: native β-CD, heptakis(2,6-di-O- methyl)-β-CD, and 6-O-α-d-glucosyl-β-CD) with OH-substituted naphthalenes (2-naphthol, 2,3-dihydroxynaphthalene, and 2,6- dihydroxynaphthalene) were determined from the induced chemical shifts of NMR measurements for inclusion complexes: K = 188-1,250 mol-1 dm 3. The modified β-CDs form stable 1:1 inclusion complexes with OH-substituted naphthalenes, and the high stability of inclusion complexes of 2,6-dihydroxynaphthalene having a hydrophobic body and hydrophilic ends is shown. In addition, the structures of inclusion complexes were characterized by 2D ROESY NMR measurements. The differences in the structure of the inclusion complexes were observed for three kinds of naphthol guest molecules. Based on the results, the inclusion abilities enhanced by methylation of the OH groups at the CD rim or the side chain of branched β-CD are discussed.

AB - The equilibrium constants (K) for the inclusion complexation of three kinds of β-cyclodextrins (β-CDs: native β-CD, heptakis(2,6-di-O- methyl)-β-CD, and 6-O-α-d-glucosyl-β-CD) with OH-substituted naphthalenes (2-naphthol, 2,3-dihydroxynaphthalene, and 2,6- dihydroxynaphthalene) were determined from the induced chemical shifts of NMR measurements for inclusion complexes: K = 188-1,250 mol-1 dm 3. The modified β-CDs form stable 1:1 inclusion complexes with OH-substituted naphthalenes, and the high stability of inclusion complexes of 2,6-dihydroxynaphthalene having a hydrophobic body and hydrophilic ends is shown. In addition, the structures of inclusion complexes were characterized by 2D ROESY NMR measurements. The differences in the structure of the inclusion complexes were observed for three kinds of naphthol guest molecules. Based on the results, the inclusion abilities enhanced by methylation of the OH groups at the CD rim or the side chain of branched β-CD are discussed.

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KW - Inclusion complex

KW - Naphthols

KW - NMR

KW - ROESY

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