Anion recognition by urea and thiourea groups: Remarkably simple neutral receptors for dihydrogenphosphate

Seiichi Nishizawa, Philippe Bühlmann, Masatoshi Iwao, Yoshio Umezawa

Research output: Contribution to journalArticlepeer-review

206 Citations (Scopus)

Abstract

A bis-urea and a bis-thiourea host, both derived in only one step from 1,3-bis(aminomethyl)benzene, are shown to bind dihydrogenphosphate selectively over various other anions (H2PO4- > CH3COO- > Cl- > HSO4- > NO3- > ClO4-). The much stronger binding of H2PO4- by the bis-thiourea is rationalized by the stronger H-bond donor strength of the thiourea groups and the binding selectivity is explained in terms of the complex geometry and the basicity of the guest anions. The lack of self-association and the changes in the UV spectrum upon complexation make bis-thiourea hosts a promising new class of neutral receptors for dihydrogenphosphate.

Original languageEnglish
Pages (from-to)6483-6486
Number of pages4
JournalTetrahedron Letters
Volume36
Issue number36
DOIs
Publication statusPublished - 1995 Sep 4
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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