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

被引：38

作者：

Albrecht, Merwe ^{[1
]}

Soloshonok, Vadim A. ^{[2
,3
]}

Schrader, Lena ^{[1
]}

Yasumoto, Manabu ^{[4
]}

Suhm, Martin A. ^{[1
]}

机构：

[1] Univ Gottingen, Inst Phys Chem, D-37077 Gottingen, Germany

[2] Univ Oklahoma, Dept Chem & Biochem, Norman, OK 73019 USA

[3] Natl Acad Sci Ukraine, Inst Bioorgan Chem & Petrochem, UA-02660 Kiev 94, Ukraine

[4] Cent Glass Co, Kawagoe, Saitama 3501151, Japan

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2010年 / 131卷 / 04期

关键词：

Eutectic; Sublimation; Chirality; Dimer; Racemate; Infrared; GAS-PHASE; PREBIOTIC CONDITIONS; ACHIRAL PHASE; SOLID-STATE; SEPARATION; CHROMATOGRAPHY; HOMOCHIRALITY; AMPLIFICATION; DISTILLATION; ENANTIOMORPH;

D O I：

10.1016/j.jfluchem.2009.11.015

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A mass-spectrometric determination of the sublimation pressure diagram of alpha-(trifluoromethyl)-lactic acid as a function of its enantiomeric composition at 293 K shows that the racemic crystals have a 38 +/- 15% higher volatility than the enantiomerically pure crystals and the sublimation eutectic has a 55 +/- 10% higher vapor pressure. These data indicate a possibility for thermodynamically controlled enantiomeric enrichment of the residual material via sublimation of samples of higher than 35 +/- 10% ee. The vibrational spectroscopy of isolated (S,S) and (S,R) dimers in supersonic jets shows that chirality recognition effects are restricted to larger clusters. This is a consequence of the rigid planar carboxylic acid binding motif. (C) 2009 Elsevier B.V. All rights reserved.

引用

页码：495 / 504

页数：10

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