A practical solvating agent for the chiral NMR discrimination of carboxylic acids

Seon Mi Kim, Kihang Choi

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

A bisimidazoline compound has been prepared as a new chiral solvating agent starting from isophthalaldehyde and (S,S)-1,2-diphenylethylenediamine through a single-step synthesis. In the presence of one equivalent of this reagent, carboxylic acid racemates show 1H NMR chemical shift nonequivalences large enough for the discrimination of the enantiomers. Studies with related compounds showed that the 1,3-disubstituted structure is crucial for the acid-solvating ability of the bisimidazoline compound.

Original languageEnglish
Pages (from-to)4747-4750
Number of pages4
JournalEuropean Journal of Organic Chemistry
Issue number25
DOIs
Publication statusPublished - 2011 Sep 1

Fingerprint

Enantiomers
enantiomers
Chemical shift
Carboxylic Acids
carboxylic acids
reagents
chemical equilibrium
discrimination
Nuclear magnetic resonance
nuclear magnetic resonance
acids
Acids
synthesis
1,2-dianilinoethane

Keywords

  • Chiral auxiliaries
  • Chirality
  • Enantiomeric purity
  • NMR spectroscopy

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry

Cite this

A practical solvating agent for the chiral NMR discrimination of carboxylic acids. / Kim, Seon Mi; Choi, Kihang.

In: European Journal of Organic Chemistry, No. 25, 01.09.2011, p. 4747-4750.

Research output: Contribution to journalArticle

@article{db5969a27e5c40b198cdfbbf4f3d59b8,
title = "A practical solvating agent for the chiral NMR discrimination of carboxylic acids",
abstract = "A bisimidazoline compound has been prepared as a new chiral solvating agent starting from isophthalaldehyde and (S,S)-1,2-diphenylethylenediamine through a single-step synthesis. In the presence of one equivalent of this reagent, carboxylic acid racemates show 1H NMR chemical shift nonequivalences large enough for the discrimination of the enantiomers. Studies with related compounds showed that the 1,3-disubstituted structure is crucial for the acid-solvating ability of the bisimidazoline compound.",
keywords = "Chiral auxiliaries, Chirality, Enantiomeric purity, NMR spectroscopy",
author = "Kim, {Seon Mi} and Kihang Choi",
year = "2011",
month = "9",
day = "1",
doi = "10.1002/ejoc.201100692",
language = "English",
pages = "4747--4750",
journal = "Annalen der Pharmacie",
issn = "0075-4617",
publisher = "Wiley-VCH Verlag",
number = "25",

}

TY - JOUR

T1 - A practical solvating agent for the chiral NMR discrimination of carboxylic acids

AU - Kim, Seon Mi

AU - Choi, Kihang

PY - 2011/9/1

Y1 - 2011/9/1

N2 - A bisimidazoline compound has been prepared as a new chiral solvating agent starting from isophthalaldehyde and (S,S)-1,2-diphenylethylenediamine through a single-step synthesis. In the presence of one equivalent of this reagent, carboxylic acid racemates show 1H NMR chemical shift nonequivalences large enough for the discrimination of the enantiomers. Studies with related compounds showed that the 1,3-disubstituted structure is crucial for the acid-solvating ability of the bisimidazoline compound.

AB - A bisimidazoline compound has been prepared as a new chiral solvating agent starting from isophthalaldehyde and (S,S)-1,2-diphenylethylenediamine through a single-step synthesis. In the presence of one equivalent of this reagent, carboxylic acid racemates show 1H NMR chemical shift nonequivalences large enough for the discrimination of the enantiomers. Studies with related compounds showed that the 1,3-disubstituted structure is crucial for the acid-solvating ability of the bisimidazoline compound.

KW - Chiral auxiliaries

KW - Chirality

KW - Enantiomeric purity

KW - NMR spectroscopy

UR - http://www.scopus.com/inward/record.url?scp=80051955688&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=80051955688&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201100692

DO - 10.1002/ejoc.201100692

M3 - Article

AN - SCOPUS:80051955688

SP - 4747

EP - 4750

JO - Annalen der Pharmacie

JF - Annalen der Pharmacie

SN - 0075-4617

IS - 25

ER -