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Solvent-catalyzed ring-chain-ring tautomerization in axially chiral compounds

Asli Yildirim, FFethiye Aylin Sungur Konuklar, Saron Catak UGent, Veronique Van Speybroeck UGent, Michel Waroquier UGent, Ilknur Dogan and Viktorya Aviyente (2012) CHEMISTRY-A EUROPEAN JOURNAL. 18(40). p.12725-12732
abstract
The mechanism of ring-chain-ring tautomerization and the prominent effect of the solvent environment have been computationally investigated in an effort to explain the enantiomeric interconversion observed in 2-oxazolidinone derivatives, heterocyclic analogues of biphenyl atropisomers, which were isolated as single stable enantiomers and have the potential to be used as axially chiral catalysts. This study has shed light on the identity of the intermediate species involved in the ring-chain-ring tautomerization process as well as the catalytic effect of polar protic solvents. These mechanistic details will prove very useful in predicting and understanding ring-chain tautomeric equilibria in similar heterocyclic systems and will further enable experimentalists to devise appropriate experimental conditions in which axially chiral catalysts remain stable as single enantiomers.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
DENSITY-FUNCTIONAL THEORY, MOLECULAR-ORBITAL METHODS, THERMOCHEMICAL KINETICS, tautomerization, microsolvation, density functional calculations, chirality, biaryls, NONCOVALENT INTERACTIONS, INSULIN SENSITIZERS, ELECTRON-DENSITY, MP2 ENERGY, MECHANISM, ATROPISOMERS, DERIVATIVES
journal title
CHEMISTRY-A EUROPEAN JOURNAL
Chem.-Eur. J.
volume
18
issue
40
pages
12725 - 12732
Web of Science type
Article
Web of Science id
000309238400024
JCR category
CHEMISTRY, MULTIDISCIPLINARY
JCR impact factor
5.831 (2012)
JCR rank
21/150 (2012)
JCR quartile
1 (2012)
ISSN
0947-6539
DOI
10.1002/chem.201200363
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
3040441
handle
http://hdl.handle.net/1854/LU-3040441
date created
2012-11-05 08:29:56
date last changed
2012-11-05 11:50:57
@article{3040441,
  abstract     = {The mechanism of ring-chain-ring tautomerization and the prominent effect of the solvent environment have been computationally investigated in an effort to explain the enantiomeric interconversion observed in 2-oxazolidinone derivatives, heterocyclic analogues of biphenyl atropisomers, which were isolated as single stable enantiomers and have the potential to be used as axially chiral catalysts. This study has shed light on the identity of the intermediate species involved in the ring-chain-ring tautomerization process as well as the catalytic effect of polar protic solvents. These mechanistic details will prove very useful in predicting and understanding ring-chain tautomeric equilibria in similar heterocyclic systems and will further enable experimentalists to devise appropriate experimental conditions in which axially chiral catalysts remain stable as single enantiomers.},
  author       = {Yildirim, Asli and Konuklar, FFethiye Aylin Sungur and Catak, Saron and Van Speybroeck, Veronique and Waroquier, Michel and Dogan, Ilknur and Aviyente, Viktorya},
  issn         = {0947-6539},
  journal      = {CHEMISTRY-A EUROPEAN JOURNAL},
  keyword      = {DENSITY-FUNCTIONAL THEORY,MOLECULAR-ORBITAL METHODS,THERMOCHEMICAL KINETICS,tautomerization,microsolvation,density functional calculations,chirality,biaryls,NONCOVALENT INTERACTIONS,INSULIN SENSITIZERS,ELECTRON-DENSITY,MP2 ENERGY,MECHANISM,ATROPISOMERS,DERIVATIVES},
  language     = {eng},
  number       = {40},
  pages        = {12725--12732},
  title        = {Solvent-catalyzed ring-chain-ring tautomerization in axially chiral compounds},
  url          = {http://dx.doi.org/10.1002/chem.201200363},
  volume       = {18},
  year         = {2012},
}

Chicago
Yildirim, Asli, Ffethiye Aylin Sungur Konuklar, Saron Catak, Veronique Van Speybroeck, Michel Waroquier, Ilknur Dogan, and Viktorya Aviyente. 2012. “Solvent-catalyzed Ring-chain-ring Tautomerization in Axially Chiral Compounds.” Chemistry-a European Journal 18 (40): 12725–12732.
APA
Yildirim, A., Konuklar, Ff. A. S., Catak, S., Van Speybroeck, V., Waroquier, M., Dogan, I., & Aviyente, V. (2012). Solvent-catalyzed ring-chain-ring tautomerization in axially chiral compounds. CHEMISTRY-A EUROPEAN JOURNAL, 18(40), 12725–12732.
Vancouver
1.
Yildirim A, Konuklar FfAS, Catak S, Van Speybroeck V, Waroquier M, Dogan I, et al. Solvent-catalyzed ring-chain-ring tautomerization in axially chiral compounds. CHEMISTRY-A EUROPEAN JOURNAL. 2012;18(40):12725–32.
MLA
Yildirim, Asli, Ffethiye Aylin Sungur Konuklar, Saron Catak, et al. “Solvent-catalyzed Ring-chain-ring Tautomerization in Axially Chiral Compounds.” CHEMISTRY-A EUROPEAN JOURNAL 18.40 (2012): 12725–12732. Print.