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

Kyu-Sung Jeong, Woo Park Jong, Lag Cho Young

Research output: Contribution to journalArticle

41 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 languageEnglish
Pages (from-to)2795-2798
Number of pages4
JournalTetrahedron Letters
Volume37
Issue number16
DOIs
Publication statusPublished - 1996 Apr 15

Fingerprint

Crown Ethers
Molecular recognition
Dicarboxylic Acids
Dimethyl Sulfoxide
Isomers
Hydrogen
Hydrogen bonds
Salts
Association reactions
Ions
Derivatives
adipic acid
1,5-dichloroanthraquinone

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

@article{df3ee04ea4be494a9e88b253b15b7ad3,
title = "Molecular recognition of dicarboxylate ions by bis-phenylureas derived from a new dicarboxylic acid",
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 = "Kyu-Sung Jeong and Jong, {Woo Park} and Young, {Lag Cho}",
year = "1996",
month = "4",
day = "15",
doi = "10.1016/0040-4039(96)00431-5",
language = "English",
volume = "37",
pages = "2795--2798",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "16",

}

Molecular recognition of dicarboxylate ions by bis-phenylureas derived from a new dicarboxylic acid. / Jeong, Kyu-Sung; Jong, Woo Park; Young, Lag Cho.

In: Tetrahedron Letters, Vol. 37, No. 16, 15.04.1996, p. 2795-2798.

Research output: Contribution to journalArticle

TY - JOUR

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

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.

UR - http://www.scopus.com/inward/record.url?scp=0343930708&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0343930708&partnerID=8YFLogxK

U2 - 10.1016/0040-4039(96)00431-5

DO - 10.1016/0040-4039(96)00431-5

M3 - Article

AN - SCOPUS:0343930708

VL - 37

SP - 2795

EP - 2798

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 16

ER -