Stereochemistry and thermodynamics of the inclusion of aliphatic and aromatic anionic guests in a tetracationic calix[4]arene in acidic and neutral aqueous solutions

Carmelo Sgarlata, Carmela Bonaccorso, Fabio Giuseppe Gulino, Valeria Zito, Giuseppe Arena, Domenico Sciotto

Research output: Contribution to journalArticle

Abstract

A cationic calix[4]arene derivative binds both aliphatic and aromatic anions in aqueous solution thanks to concerted electrostatic and hydrophobic interactions. 1H NMR and potentiometric data show that the host flexibility changes as a function of pH. 1H NMR and isothermal titration calorimetry (ITC) studies, also supported by ESI-MS data, show that inclusion yields supramolecular complexes of the guest⊂host type only. Binding becomes weaker as the pH increases due to rigidification of the host in neutral aqueous solutions, and is enthalpically favoured for all the supramolecular complexes, regardless of pH.

Original languageEnglish
Pages (from-to)991-997
Number of pages7
JournalNew Journal of Chemistry
Volume33
Issue number5
DOIs
Publication statusPublished - 2009

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ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Materials Chemistry

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