Advanced search
1 file | 1.28 MB

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

(2012) CHEMISTRY-A EUROPEAN JOURNAL. 18(40). p.12725-12732
Author
Organization
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.
Keywords
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

Downloads

  • (...).pdf
    • full text
    • |
    • UGent only
    • |
    • PDF
    • |
    • 1.28 MB

Citation

Please use this url to cite or link to this publication:

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.
@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},
}

Altmetric
View in Altmetric
Web of Science
Times cited: