A selective acetate anion binding receptor: Participation via cationic CH3 donors

Thiravidamani Senthil Pandian, Venkatesan Srinivasadesikan, Ming-Chang Lin, Jongmin Kang*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

A novel receptor 1, which has only C-H hydrogen bonds as recognition element has been designed and synthesized. The receptor 1 utilizes cationic CH3 in 2-methyl benzimidazole and naphthalene benzylic C-H as hydrogen bonding donor. The binding cavity formed in receptor 1 prefers to accommodate small negatively charged atom such as oxygen. Therefore, acetate and nitrite show strong affinity for receptor 1 in acetonitrile due to negatively charged oxygen in them. In addition, the order of binding affinity for halides are Br->Cl->I-. These results reflect the size and basicities of halides. Further, 1H NMR titration of halide clearly indicates the anion-π interaction. The experimental data from UV-vis, fluorescence and 1H NMR titration are consistent with DFT results.

Original languageEnglish
Pages (from-to)8350-8356
Number of pages7
JournalTetrahedron
Volume71
Issue number43
DOIs
StatePublished - 28 Oct 2015

Keywords

  • Acetate
  • Anion receptor
  • Anion-π interaction
  • C-H hydrogen bonds
  • Nitrite

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