Characteristic effects of substituent and external pressure on group-inclusion complexation with p-sulfonatocalix[8]arene and γ-cyclodextrin

Keitaro Miyazono, Tadashi Hanaya, Yoshimi Sueishi

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

By synthesizing unique nitroxide probes (α-substituted phenyl-2,4,6-trimethoxybenzyl(t-butyl)nitroxide), we have shown that p-sulfonatocalix[8]arene (Calix-S8) and γ-cyclodextin (γ-CD) form electron spin resonance spectroscopically separable group-inclusion complexes (α-substituted phenyl-in (R-in) and t-butyl-in complexes) and determined the group-inclusion constants of Calix-S8 and γ-CD. Using nitroxide probes, we have examined the effects of substituent and external pressure on group-inclusion complexation with Calix-S8 and γ-CD. Experiments on pressure dependence enabled us to calculate the reaction volume (ΔV) for R-in and t-butyl-in complex formations. ΔV for group-in complexation with Calix-S8 had negative values. In contrast, ΔV values for γ-CD showed positive values, which is responsible for the repelled water molecules in the CD cavity. The characteristic pressure effects on group-in complexation suggest that group recognition by γ-CD is sensitive when compared with that by Calix-S8.

Original languageEnglish
Pages (from-to)337-344
Number of pages8
JournalHigh Pressure Research
Volume34
Issue number3
DOIs
Publication statusPublished - Jul 5 2014

Fingerprint

inclusions
probes
pressure effects
pressure dependence
electron paramagnetic resonance
cavities
water
molecules

Keywords

  • calixarene
  • cyclodextrin
  • group-inclusion
  • high pressure ESR

ASJC Scopus subject areas

  • Condensed Matter Physics

Cite this

@article{c485e2fd164a45af9a3a49a4c120e059,
title = "Characteristic effects of substituent and external pressure on group-inclusion complexation with p-sulfonatocalix[8]arene and γ-cyclodextrin",
abstract = "By synthesizing unique nitroxide probes (α-substituted phenyl-2,4,6-trimethoxybenzyl(t-butyl)nitroxide), we have shown that p-sulfonatocalix[8]arene (Calix-S8) and γ-cyclodextin (γ-CD) form electron spin resonance spectroscopically separable group-inclusion complexes (α-substituted phenyl-in (R-in) and t-butyl-in complexes) and determined the group-inclusion constants of Calix-S8 and γ-CD. Using nitroxide probes, we have examined the effects of substituent and external pressure on group-inclusion complexation with Calix-S8 and γ-CD. Experiments on pressure dependence enabled us to calculate the reaction volume (ΔV) for R-in and t-butyl-in complex formations. ΔV for group-in complexation with Calix-S8 had negative values. In contrast, ΔV values for γ-CD showed positive values, which is responsible for the repelled water molecules in the CD cavity. The characteristic pressure effects on group-in complexation suggest that group recognition by γ-CD is sensitive when compared with that by Calix-S8.",
keywords = "calixarene, cyclodextrin, group-inclusion, high pressure ESR",
author = "Keitaro Miyazono and Tadashi Hanaya and Yoshimi Sueishi",
year = "2014",
month = "7",
day = "5",
doi = "10.1080/08957959.2014.947605",
language = "English",
volume = "34",
pages = "337--344",
journal = "High Pressure Research",
issn = "0895-7959",
publisher = "Taylor and Francis Ltd.",
number = "3",

}

TY - JOUR

T1 - Characteristic effects of substituent and external pressure on group-inclusion complexation with p-sulfonatocalix[8]arene and γ-cyclodextrin

AU - Miyazono, Keitaro

AU - Hanaya, Tadashi

AU - Sueishi, Yoshimi

PY - 2014/7/5

Y1 - 2014/7/5

N2 - By synthesizing unique nitroxide probes (α-substituted phenyl-2,4,6-trimethoxybenzyl(t-butyl)nitroxide), we have shown that p-sulfonatocalix[8]arene (Calix-S8) and γ-cyclodextin (γ-CD) form electron spin resonance spectroscopically separable group-inclusion complexes (α-substituted phenyl-in (R-in) and t-butyl-in complexes) and determined the group-inclusion constants of Calix-S8 and γ-CD. Using nitroxide probes, we have examined the effects of substituent and external pressure on group-inclusion complexation with Calix-S8 and γ-CD. Experiments on pressure dependence enabled us to calculate the reaction volume (ΔV) for R-in and t-butyl-in complex formations. ΔV for group-in complexation with Calix-S8 had negative values. In contrast, ΔV values for γ-CD showed positive values, which is responsible for the repelled water molecules in the CD cavity. The characteristic pressure effects on group-in complexation suggest that group recognition by γ-CD is sensitive when compared with that by Calix-S8.

AB - By synthesizing unique nitroxide probes (α-substituted phenyl-2,4,6-trimethoxybenzyl(t-butyl)nitroxide), we have shown that p-sulfonatocalix[8]arene (Calix-S8) and γ-cyclodextin (γ-CD) form electron spin resonance spectroscopically separable group-inclusion complexes (α-substituted phenyl-in (R-in) and t-butyl-in complexes) and determined the group-inclusion constants of Calix-S8 and γ-CD. Using nitroxide probes, we have examined the effects of substituent and external pressure on group-inclusion complexation with Calix-S8 and γ-CD. Experiments on pressure dependence enabled us to calculate the reaction volume (ΔV) for R-in and t-butyl-in complex formations. ΔV for group-in complexation with Calix-S8 had negative values. In contrast, ΔV values for γ-CD showed positive values, which is responsible for the repelled water molecules in the CD cavity. The characteristic pressure effects on group-in complexation suggest that group recognition by γ-CD is sensitive when compared with that by Calix-S8.

KW - calixarene

KW - cyclodextrin

KW - group-inclusion

KW - high pressure ESR

UR - http://www.scopus.com/inward/record.url?scp=84908553750&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84908553750&partnerID=8YFLogxK

U2 - 10.1080/08957959.2014.947605

DO - 10.1080/08957959.2014.947605

M3 - Article

VL - 34

SP - 337

EP - 344

JO - High Pressure Research

JF - High Pressure Research

SN - 0895-7959

IS - 3

ER -