Probing the Entropic Effect in Molecular Noncovalent Interactions between Resin-Bound Polybrominated Arenes and Small Substrates

Masanori Yamamoto, Miyuki Obara, Keisuke Ochi, Atsushi Yamamoto, Katsuhiko Takenaka, Tsunehiro Tanaka, Kazunori Sato

Research output: Contribution to journalArticle

Abstract

The associative interaction between resin-bound polybrominated arenes and small molecules was analyzed by using various spectroscopic techniques as well as a synthetic molecular model to establish the thermodynamics. The binding in acetonitrile was three orders of magnitude stronger than that in methanol, partly owing to the tertiary conformational gating of the resin that controls the entropic terms. By using the entropic superiority, the associative binding of up to 3×104 m−1 is achieved with the non-biological system. A modified Hill plot for the quantitative analysis of bindings was also devised, which enabled the interactions at the molecular level to be elucidated.

Original languageEnglish
Pages (from-to)820-824
Number of pages5
JournalChemPlusChem
Volume83
Issue number9
DOIs
Publication statusPublished - 2018 Sep

Keywords

  • adsorption
  • entropy
  • liquid chromatography
  • noncovalent interactions
  • solid-phase extraction

ASJC Scopus subject areas

  • Chemistry(all)

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