Molecular recognition of dicarboxylate ions by bis-phenylureas derived from a new dicarboxylic acid

Kyu Sung Jeong; Woo Park Jong; Lag Cho Young

doi:10.1016/0040-4039(96)00431-5

Molecular recognition of dicarboxylate ions by bis-phenylureas derived from a new dicarboxylic acid

Kyu Sung Jeong, Woo Park Jong, Lag Cho Young

Department of Chemistry

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

14 Citations (Scopus)

Abstract

A new dicarboxylic acid 4 was synthesized from 1,5-dichloroanthraquinone (1) and modified to ditopic receptors for binding of diammonium and dicarboxylate salts by multiple hydrogen bonds. The cis and trans isomers of 4 were assigned by the relative binding affinities of the bis(crown ether) derivatives, 5a and 5b to alkyl diammonium dipicrates. The association constants (K(a)) between p-substituted bis-phenylureas and adipate vary from 5 x 10² to 2 x 10⁴ M^-1 in DMSO-d₆, depending on substituents in the phenyl ring.

Original language	English
Pages (from-to)	2795-2798
Number of pages	4
Journal	Tetrahedron Letters
Volume	37
Issue number	16
DOIs	https://doi.org/10.1016/0040-4039(96)00431-5
Publication status	Published - 1996 Apr 15

Bibliographical note

Funding Information:
Acknowledgement This work was financially supported by the Basic Science Research Institute

Funding Information:
Program, Ministry of Education (Project No. BSRI-94-3422).

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/0040-4039(96)00431-5

Cite this

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abstract = "A new dicarboxylic acid 4 was synthesized from 1,5-dichloroanthraquinone (1) and modified to ditopic receptors for binding of diammonium and dicarboxylate salts by multiple hydrogen bonds. The cis and trans isomers of 4 were assigned by the relative binding affinities of the bis(crown ether) derivatives, 5a and 5b to alkyl diammonium dipicrates. The association constants (K(a)) between p-substituted bis-phenylureas and adipate vary from 5 x 102 to 2 x 104 M-1 in DMSO-d6, depending on substituents in the phenyl ring.",

author = "Jeong, {Kyu Sung} and Jong, {Woo Park} and Young, {Lag Cho}",

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T1 - Molecular recognition of dicarboxylate ions by bis-phenylureas derived from a new dicarboxylic acid

AU - Jeong, Kyu Sung

AU - Jong, Woo Park

AU - Young, Lag Cho

N1 - Funding Information: Acknowledgement This work was financially supported by the Basic Science Research Institute Funding Information: Program, Ministry of Education (Project No. BSRI-94-3422).

PY - 1996/4/15

Y1 - 1996/4/15

N2 - A new dicarboxylic acid 4 was synthesized from 1,5-dichloroanthraquinone (1) and modified to ditopic receptors for binding of diammonium and dicarboxylate salts by multiple hydrogen bonds. The cis and trans isomers of 4 were assigned by the relative binding affinities of the bis(crown ether) derivatives, 5a and 5b to alkyl diammonium dipicrates. The association constants (K(a)) between p-substituted bis-phenylureas and adipate vary from 5 x 102 to 2 x 104 M-1 in DMSO-d6, depending on substituents in the phenyl ring.

AB - A new dicarboxylic acid 4 was synthesized from 1,5-dichloroanthraquinone (1) and modified to ditopic receptors for binding of diammonium and dicarboxylate salts by multiple hydrogen bonds. The cis and trans isomers of 4 were assigned by the relative binding affinities of the bis(crown ether) derivatives, 5a and 5b to alkyl diammonium dipicrates. The association constants (K(a)) between p-substituted bis-phenylureas and adipate vary from 5 x 102 to 2 x 104 M-1 in DMSO-d6, depending on substituents in the phenyl ring.

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Molecular recognition of dicarboxylate ions by bis-phenylureas derived from a new dicarboxylic acid

Abstract

Bibliographical note

All Science Journal Classification (ASJC) codes

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