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

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

doi:10.1016/S0040-4020(96)01094-0

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 journal › Article › peer-review

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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 language	English (US)
Pages (from-to)	1647-1654
Number of pages	8
Journal	Tetrahedron
Volume	53
Issue number	5
DOIs	https://doi.org/10.1016/S0040-4020(96)01094-0
State	Published - Feb 3 1997
Externally published	Yes

Bibliographical note

Funding Information:
We are indebted to Dr. M. Sasaki for assistancei n mass spectroscopy and S. Amemiya for various interestingd iscussions. This work was supportedb y the Ministry of Education, Science and Culture, Japan, the TokuyamaS cienceF oundationa nd a SasakawaS cientific ResearchG rant from the Japan Science Society.

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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).",

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AU - Bühlmann, Philippe

AU - Nishizawa, Seiichi

AU - Xiao, Kang Ping

AU - Umezawa, Yoshio

N1 - Funding Information: We are indebted to Dr. M. Sasaki for assistancei n mass spectroscopy and S. Amemiya for various interestingd iscussions. This work was supportedb y the Ministry of Education, Science and Culture, Japan, the TokuyamaS cienceF oundationa nd a SasakawaS cientific ResearchG rant from the Japan Science Society.

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