The effect of the electron density distribution of guest on the entropy change during complex formation of calix[6]arene hexasulfonate host with ortho- and para-cresols as guests

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Abstract

The π-π interaction-based inclusion complexation of calix[6]arene hexasulfonate as host with neutral aromatic guest molecules was studied in aqueous media. To vary the distribution of electron density on the guest's aromatic rings, the phenol parent compound was substituted in the para - or ortho - positions with CH 3 group. To study the interaction between calixarene and the guests, PL, DSC and quantum-chemical methods were used. The results indicate 1:1 stoichiometry of the formed host-guest complexes. Although the enthalpy change during complex formation of calixarene with p - or o -cresol are the same, the Gibbs free energy change is significantly higher in the case of calixarene - o -cresol complexes. This property is due to the unexpected entropy change during the complex formation. Using molecular dynamic calculations, a guest-induced redistribution of the electron density on the calixarene rings, followed by the restructuring of the solvent molecules was identified as a background of this unexpected entropy change at molecular level.

Original languageEnglish
Pages (from-to)245-250
Number of pages6
JournalSupramolecular Chemistry
Volume18
Issue number3
DOIs
Publication statusPublished - May 1 2006

Keywords

  • Calixarene
  • Complexation thermodynamics
  • Host-guest complexes

ASJC Scopus subject areas

  • Chemistry(all)

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