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

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

研究成果: Article

234 引用 (Scopus)

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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).

元の言語English
ページ(範囲)1647-1654
ページ数8
ジャーナルTetrahedron
53
発行部数5
DOI
出版物ステータスPublished - 1997 2 3

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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