Self-disproportionation of enantiomers via achiral chromatography: a warning and an extra dimension in optical purifications

Reply to the ‘Comment on “Theoretical investigations into the enantiomeric and racemic forms of α-(trifluoromethyl)lactic acid”’ by M. A. Suhm and M. Albrecht, Phys. Chem. Chem. Phys., 2011, 13, DOI: 10.1039/c0cp02455d

(2011) Ralf Tonner et al.   PHYSICAL CHEMISTRY CHEMICAL PHYSICS

Comment on “Theoretical investigations into the enantiomeric and racemic forms of α-(trifluoromethyl)lactic acid” by R. Tonner, V. A. Soloshonok and P. Schwerdtfeger, Phys. Chem. Chem. Phys., 2011, 13, 811-817

(2011) M. A. Suhm et al.   PHYSICAL CHEMISTRY CHEMICAL PHYSICS

A simple explanation of the enhancement or depletion of the enantiomeric excess in the partial sublimation of enantiomerically enriched amino acids

(2010) Aurélien Bellec et al.   CHEMICAL COMMUNICATIONS

Asymmetric Construction of Stereogenic Carbon Centers Featuring a Trifluoromethyl Group from Prochiral Trifluoromethylated Substrates

(2010) Jing Nie et al.   CHEMICAL REVIEWS

First principle lattice energy calculations for enantiopure and racemic crystals of α-(trifluoromethyl)lactic acid: Is self-disproportionation of enantiomers controlled by thermodynamic stability of crystals?

(2010) Seiji Tsuzuki et al.   JOURNAL OF FLUORINE CHEMISTRY

Separation of non-racemic mixtures of enantiomers: an essential part of optical resolution

(2010) Ferenc Faigl et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Theoretical investigations into the enantiomeric and racemic forms of α-(trifluoromethyl)lactic acid

(2010) Ralf Tonner et al.   PHYSICAL CHEMISTRY CHEMICAL PHYSICS

Nonlinear effects in enantioselective chromatography: prediction of unusual elution profiles of enantiomers in non-racemic mixtures on an achiral stationary phase doped with small amounts of a chiral selector

(2010) Oliver Trapp et al.   TETRAHEDRON-ASYMMETRY

Rational application of self-disproportionation of enantiomers via sublimation—a novel methodological dimension for enantiomeric purifications

(2010) Hisanori Ueki et al.   TETRAHEDRON-ASYMMETRY

Self-disproportionation of enantiomers of α-trifluoromethyl lactic acid amides via sublimation

(2009) Manabu Yasumoto et al.   JOURNAL OF FLUORINE CHEMISTRY

Self-disproportionation of enantiomers of isopropyl 3,3,3-(trifluoro)lactate via sublimation: Sublimation rates vs. enantiomeric composition

(2009) Manabu Yasumoto et al.   JOURNAL OF FLUORINE CHEMISTRY

Asymmetric synthesis of fluorine-containing amines, amino alcohols, α- and β-amino acids mediated by chiral sulfinyl group

(2009) Alexander E. Sorochinsky et al.   JOURNAL OF FLUORINE CHEMISTRY

Attempts to explain the self-disproportionation observed in the partial sublimation of enantiomerically enriched carboxylic acids

(2009) Aurélien Bellec et al.   JOURNAL OF FLUORINE CHEMISTRY

Discrimination of enantiomeric excess of optically active trifluorolactate by distillation: Evidence for a multi-center hydrogen bonding network in the liquid state

(2009) Toshimasa Katagiri et al.   JOURNAL OF FLUORINE CHEMISTRY

Chirality-dependent sublimation of -(trifluoromethyl)-lactic acid: Relative vapor pressures of racemic, eutectic, and enantiomerically pure forms, and vibrational spectroscopy of isolated (S,S) and (S,R) dimers

(2009) Merwe Albrecht et al.   JOURNAL OF FLUORINE CHEMISTRY

Self-disproportionation of enantiomers of 3,3,3-trifluorolactic acid amides via sublimation

(2009) Manabu Yasumoto et al.   JOURNAL OF FLUORINE CHEMISTRY

Atropisomeric lactam chemistry: catalytic enantioselective synthesis, application to asymmetric enolate chemistry and synthesis of key intermediates for NET inhibitors

(2009) Masashi Takahashi et al.   TETRAHEDRON

Separation of Racemate from Excess Enantiomer of Chiral Nonracemic Compounds via Density Gradient Ultracentrifugation

(2008) Yitzhak Mastai et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Understanding organofluorine chemistry. An introduction to the C–F bond

(2007) David O'Hagan   CHEMICAL SOCIETY REVIEWS