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

Seiichi Nishizawa; Philippe Bühlmann; Masatoshi Iwao; Yoshio Umezawa

doi:10.1016/0040-4039(95)01296-T

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

Seiichi Nishizawa, Philippe Bühlmann, Masatoshi Iwao, Yoshio Umezawa

SCI - Chemistry

The University of Tokyo

Research output: Contribution to journal › Article › peer-review

215 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 language	English
Pages (from-to)	6483-6486
Number of pages	4
Journal	Tetrahedron Letters
Volume	36
Issue number	36
DOIs	https://doi.org/10.1016/0040-4039(95)01296-T
Publication status	Published - 1995 Sept 4

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title = "Anion recognition by urea and thiourea groups: Remarkably simple neutral receptors for dihydrogenphosphate",

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.",

author = "Seiichi Nishizawa and Philippe B{\"u}hlmann and Masatoshi Iwao and Yoshio Umezawa",

note = "Funding Information: Acknowledgments. This work was supported by the Nissan Science Foundation, a Sasakawa Scientific Research Grant from The Japan Science Society, and the Ministry of Education, Science and Culture, Japan.",

year = "1995",

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doi = "10.1016/0040-4039(95)01296-T",

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TY - JOUR

T1 - Anion recognition by urea and thiourea groups

T2 - Remarkably simple neutral receptors for dihydrogenphosphate

AU - Nishizawa, Seiichi

AU - Bühlmann, Philippe

AU - Iwao, Masatoshi

AU - Umezawa, Yoshio

N1 - Funding Information: Acknowledgments. This work was supported by the Nissan Science Foundation, a Sasakawa Scientific Research Grant from The Japan Science Society, and the Ministry of Education, Science and Culture, Japan.

PY - 1995/9/4

Y1 - 1995/9/4

N2 - 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.

AB - 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.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

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

Abstract

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