Chirality sensing by nonchiral porphines

Jan Labuta, Shinsuke Ishihara, Atsuomi Shundo, Satoshi Arai, Shinji Takeoka, Katsuhiko Ariga, Jonathan P. Hill

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

Let's split the difference: Nonchiral porphine macrocycles have been used as chemical shift agents for the determination of the enantiomeric excesses of chiral carboxylic acids. This method is based on the observation of the relative splitting induced in the 1H NMR resonances of the porphine protons. A mechanism for the recognition based on the fast exchange of the guest molecules has been proposed (see scheme).

Original languageEnglish
Pages (from-to)3558-3561
Number of pages4
JournalChemistry - A European Journal
Volume17
Issue number13
DOIs
Publication statusPublished - 2011 Mar 21

Fingerprint

Chirality
Chemical shift
Carboxylic acids
Protons
Nuclear magnetic resonance
Molecules
Carboxylic Acids
porphine

Keywords

  • carboxylic acids
  • chiral solvating agents
  • enantiomeric excess
  • NMR spectroscopy
  • porphyrinoids

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Labuta, J., Ishihara, S., Shundo, A., Arai, S., Takeoka, S., Ariga, K., & Hill, J. P. (2011). Chirality sensing by nonchiral porphines. Chemistry - A European Journal, 17(13), 3558-3561. https://doi.org/10.1002/chem.201100052

Chirality sensing by nonchiral porphines. / Labuta, Jan; Ishihara, Shinsuke; Shundo, Atsuomi; Arai, Satoshi; Takeoka, Shinji; Ariga, Katsuhiko; Hill, Jonathan P.

In: Chemistry - A European Journal, Vol. 17, No. 13, 21.03.2011, p. 3558-3561.

Research output: Contribution to journalArticle

Labuta, J, Ishihara, S, Shundo, A, Arai, S, Takeoka, S, Ariga, K & Hill, JP 2011, 'Chirality sensing by nonchiral porphines', Chemistry - A European Journal, vol. 17, no. 13, pp. 3558-3561. https://doi.org/10.1002/chem.201100052
Labuta J, Ishihara S, Shundo A, Arai S, Takeoka S, Ariga K et al. Chirality sensing by nonchiral porphines. Chemistry - A European Journal. 2011 Mar 21;17(13):3558-3561. https://doi.org/10.1002/chem.201100052
Labuta, Jan ; Ishihara, Shinsuke ; Shundo, Atsuomi ; Arai, Satoshi ; Takeoka, Shinji ; Ariga, Katsuhiko ; Hill, Jonathan P. / Chirality sensing by nonchiral porphines. In: Chemistry - A European Journal. 2011 ; Vol. 17, No. 13. pp. 3558-3561.
@article{2716296210804e2fba4a907f71ab0940,
title = "Chirality sensing by nonchiral porphines",
abstract = "Let's split the difference: Nonchiral porphine macrocycles have been used as chemical shift agents for the determination of the enantiomeric excesses of chiral carboxylic acids. This method is based on the observation of the relative splitting induced in the 1H NMR resonances of the porphine protons. A mechanism for the recognition based on the fast exchange of the guest molecules has been proposed (see scheme).",
keywords = "carboxylic acids, chiral solvating agents, enantiomeric excess, NMR spectroscopy, porphyrinoids",
author = "Jan Labuta and Shinsuke Ishihara and Atsuomi Shundo and Satoshi Arai and Shinji Takeoka and Katsuhiko Ariga and Hill, {Jonathan P.}",
year = "2011",
month = "3",
day = "21",
doi = "10.1002/chem.201100052",
language = "English",
volume = "17",
pages = "3558--3561",
journal = "Chemistry - A European Journal",
issn = "0947-6539",
publisher = "Wiley-VCH Verlag",
number = "13",

}

TY - JOUR

T1 - Chirality sensing by nonchiral porphines

AU - Labuta, Jan

AU - Ishihara, Shinsuke

AU - Shundo, Atsuomi

AU - Arai, Satoshi

AU - Takeoka, Shinji

AU - Ariga, Katsuhiko

AU - Hill, Jonathan P.

PY - 2011/3/21

Y1 - 2011/3/21

N2 - Let's split the difference: Nonchiral porphine macrocycles have been used as chemical shift agents for the determination of the enantiomeric excesses of chiral carboxylic acids. This method is based on the observation of the relative splitting induced in the 1H NMR resonances of the porphine protons. A mechanism for the recognition based on the fast exchange of the guest molecules has been proposed (see scheme).

AB - Let's split the difference: Nonchiral porphine macrocycles have been used as chemical shift agents for the determination of the enantiomeric excesses of chiral carboxylic acids. This method is based on the observation of the relative splitting induced in the 1H NMR resonances of the porphine protons. A mechanism for the recognition based on the fast exchange of the guest molecules has been proposed (see scheme).

KW - carboxylic acids

KW - chiral solvating agents

KW - enantiomeric excess

KW - NMR spectroscopy

KW - porphyrinoids

UR - http://www.scopus.com/inward/record.url?scp=79952595399&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79952595399&partnerID=8YFLogxK

U2 - 10.1002/chem.201100052

DO - 10.1002/chem.201100052

M3 - Article

C2 - 21344527

AN - SCOPUS:79952595399

VL - 17

SP - 3558

EP - 3561

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 13

ER -