Strong hydrogen bond-mediated complexation of H2PO4- by neutral bis-thiourea hosts

Philippe Bühlmann, Seiichi Nishizawa, Kang Ping Xiao, Yoshio Umezawa

Research output: Contribution to journalArticle

234 Citations (Scopus)

Abstract

Highly preorganized bis-thiourea receptors based on a xanthene spacer selectively (H2PO4- > CH3COO- > Cl-) bind dihydrogenphosphate via multitopic hydrogen bonding, giving stronger complexes with H2PO4- than any synthetic neutral receptor known so far. The high complexation strengths are rationalized by the hydrogen bond donor strength of the thiourea groups and by host preorganization. The hydrogen bond acceptor strengths of the guest anions and, for small ions, guest solvation explain the observed selectivity of complexation in dimethyl sulfoxide (DMSO).

Original languageEnglish
Pages (from-to)1647-1654
Number of pages8
JournalTetrahedron
Volume53
Issue number5
DOIs
Publication statusPublished - 1997 Feb 3

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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