Investigation of inclusion complexation of imidazolium and pyrrolidinium chlorides with water-soluble p-sulfonatocalix[6]arene: characteristic effects of external pressure, temperature, and substituents

Yoshimi Sueishi, Yusaku Honda, Shono Fujitani, Naoya Inazumi, Tadashi Hanaya

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Using the inclusion complexation of methylene blue as a chemical indicator, the inclusion constants of imidazolium and pyrrolidinium chlorides (ionic liquids (IL)) with p-sulfonatocalix[6]arene (Calix-S6) were determined in a water–methanol mixture. In the inclusion of imidazolium chlorides, we found the characteristic inclusion constants, dependent on the length of the alkyl side chain. From the temperature effect on the inclusion, the differences in the inclusion interactions of imidazolium and pyrrolidinium ring moiety with the sulfonate groups of the Calix-S6’s portal were observed. Further, from high-pressure studies on the inclusion complexation, the volume changes caused by the conformational changes of Calix-S6 and desolvation around the guest and host molecules upon inclusion were evaluated. Based on the results, we demonstrated that the volume change related to desolvation upon inclusion plays an important role in the reaction volume for the inclusion equilibrium of IL with Calix-S6. The structures of the inclusion complexes were established from 2D ROESY NMR measurements and a volumetric study of the inclusion complexation with p-sulfonated Calix-S6 having a flexible cavity was performed.

Original languageEnglish
Pages (from-to)255-261
Number of pages7
JournalJournal of Inclusion Phenomena and Macrocyclic Chemistry
Volume86
Issue number3-4
DOIs
Publication statusPublished - Dec 1 2016

Fingerprint

S 6
Complexation
Chlorides
chlorides
inclusions
Pressure
Ionic Liquids
Temperature
Water
water
temperature
methylene blue
sulfonates
Methylene Blue
imidazole
calix(6)arene
chemical indicators
ionic liquids
liquids
Thermal effects

Keywords

  • Imidazolium chloride
  • Inclusion complexation
  • p-Sulfonatocalix[6]arene
  • Pressure effects
  • Substituent effects

ASJC Scopus subject areas

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

Cite this

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title = "Investigation of inclusion complexation of imidazolium and pyrrolidinium chlorides with water-soluble p-sulfonatocalix[6]arene: characteristic effects of external pressure, temperature, and substituents",
abstract = "Using the inclusion complexation of methylene blue as a chemical indicator, the inclusion constants of imidazolium and pyrrolidinium chlorides (ionic liquids (IL)) with p-sulfonatocalix[6]arene (Calix-S6) were determined in a water–methanol mixture. In the inclusion of imidazolium chlorides, we found the characteristic inclusion constants, dependent on the length of the alkyl side chain. From the temperature effect on the inclusion, the differences in the inclusion interactions of imidazolium and pyrrolidinium ring moiety with the sulfonate groups of the Calix-S6’s portal were observed. Further, from high-pressure studies on the inclusion complexation, the volume changes caused by the conformational changes of Calix-S6 and desolvation around the guest and host molecules upon inclusion were evaluated. Based on the results, we demonstrated that the volume change related to desolvation upon inclusion plays an important role in the reaction volume for the inclusion equilibrium of IL with Calix-S6. The structures of the inclusion complexes were established from 2D ROESY NMR measurements and a volumetric study of the inclusion complexation with p-sulfonated Calix-S6 having a flexible cavity was performed.",
keywords = "Imidazolium chloride, Inclusion complexation, p-Sulfonatocalix[6]arene, Pressure effects, Substituent effects",
author = "Yoshimi Sueishi and Yusaku Honda and Shono Fujitani and Naoya Inazumi and Tadashi Hanaya",
year = "2016",
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TY - JOUR

T1 - Investigation of inclusion complexation of imidazolium and pyrrolidinium chlorides with water-soluble p-sulfonatocalix[6]arene

T2 - characteristic effects of external pressure, temperature, and substituents

AU - Sueishi, Yoshimi

AU - Honda, Yusaku

AU - Fujitani, Shono

AU - Inazumi, Naoya

AU - Hanaya, Tadashi

PY - 2016/12/1

Y1 - 2016/12/1

N2 - Using the inclusion complexation of methylene blue as a chemical indicator, the inclusion constants of imidazolium and pyrrolidinium chlorides (ionic liquids (IL)) with p-sulfonatocalix[6]arene (Calix-S6) were determined in a water–methanol mixture. In the inclusion of imidazolium chlorides, we found the characteristic inclusion constants, dependent on the length of the alkyl side chain. From the temperature effect on the inclusion, the differences in the inclusion interactions of imidazolium and pyrrolidinium ring moiety with the sulfonate groups of the Calix-S6’s portal were observed. Further, from high-pressure studies on the inclusion complexation, the volume changes caused by the conformational changes of Calix-S6 and desolvation around the guest and host molecules upon inclusion were evaluated. Based on the results, we demonstrated that the volume change related to desolvation upon inclusion plays an important role in the reaction volume for the inclusion equilibrium of IL with Calix-S6. The structures of the inclusion complexes were established from 2D ROESY NMR measurements and a volumetric study of the inclusion complexation with p-sulfonated Calix-S6 having a flexible cavity was performed.

AB - Using the inclusion complexation of methylene blue as a chemical indicator, the inclusion constants of imidazolium and pyrrolidinium chlorides (ionic liquids (IL)) with p-sulfonatocalix[6]arene (Calix-S6) were determined in a water–methanol mixture. In the inclusion of imidazolium chlorides, we found the characteristic inclusion constants, dependent on the length of the alkyl side chain. From the temperature effect on the inclusion, the differences in the inclusion interactions of imidazolium and pyrrolidinium ring moiety with the sulfonate groups of the Calix-S6’s portal were observed. Further, from high-pressure studies on the inclusion complexation, the volume changes caused by the conformational changes of Calix-S6 and desolvation around the guest and host molecules upon inclusion were evaluated. Based on the results, we demonstrated that the volume change related to desolvation upon inclusion plays an important role in the reaction volume for the inclusion equilibrium of IL with Calix-S6. The structures of the inclusion complexes were established from 2D ROESY NMR measurements and a volumetric study of the inclusion complexation with p-sulfonated Calix-S6 having a flexible cavity was performed.

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