Issue 4, 2013
From the journal:

Chemical Communications

Unconventional preparation of racemic crystals of isopropyl 3,3,3-trifluoro-2-hydroxypropanoate and their unusual crystallographic structure: the ultimate preference for homochiral intermolecular interactions†

José Luis Aceña,a   Alexander E. Sorochinsky,ab   Toshimasa Katagiric  and  Vadim A. Soloshonok*ab  

* Corresponding authors

a Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, 20018 San Sebastián, Spain
E-mail: vadym.soloshonok@ehu.es
Fax: +34 943-015270
Tel: +34 943-015177

b IKERBASQUE, Basque Foundation for Science, 48011 Bilbao, Spain

c Department of Applied Chemistry, Faculty of Engineering, Okayama University, 3-1-1, Tsushimanaka, Kita-ku, Okayama 700-8530, Japan

Abstract

This work reports the first example of the transformation of conglomerate (R)- and (S)-crystals into racemic crystals via sublimation. Crystallographic analysis of racemic isopropyl 3,3,3-trifluoro-2-hydroxypropanoate did not reveal the highly expected heterochiral dimer indicating that this compound is capable of forming exclusively homochiral oligomers via infinite multi-centred H-bonding networks.

Graphical abstract: Unconventional preparation of racemic crystals of isopropyl 3,3,3-trifluoro-2-hydroxypropanoate and their unusual crystallographic structure: the ultimate preference for homochiral intermolecular interactions

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Article information

DOI
https://doi.org/10.1039/C2CC37491A
Article type
Communication
Submitted
13 Oct 2012
Accepted
14 Nov 2012
First published
15 Nov 2012

Chem. Commun., 2013,49, 373-375

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Unconventional preparation of racemic crystals of isopropyl 3,3,3-trifluoro-2-hydroxypropanoate and their unusual crystallographic structure: the ultimate preference for homochiral intermolecular interactions

J. L. Aceña, A. E. Sorochinsky, T. Katagiri and V. A. Soloshonok, Chem. Commun., 2013, 49, 373 DOI: 10.1039/C2CC37491A

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