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

Chemistry (Twin Cities)

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

224 Scopus citations

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 (US)
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
State	Published - Sep 4 1995

Bibliographical 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.

Publisher link

10.1016/0040-4039(95)01296-T

Find It

Find It at U of M Libraries

Cite this

@article{4435c14f446041e0bcfde71f6f4685f1,

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",

month = sep,

day = "4",

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

language = "English (US)",

volume = "36",

pages = "6483--6486",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "36",

}

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.

UR - https://www.scopus.com/pages/publications/0029143485

UR - https://www.scopus.com/pages/publications/0029143485#tab=citedBy

U2 - 10.1016/0040-4039(95)01296-T

DO - 10.1016/0040-4039(95)01296-T

M3 - Article

AN - SCOPUS:0029143485

SN - 0040-4039

VL - 36

SP - 6483

EP - 6486

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 36

ER -

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

Abstract

Bibliographical note

Publisher link

Find It

Other files and links

Fingerprint

Cite this