Synthesis 2014; 46(21): 2937-2944
DOI: 10.1055/s-0034-1378347
paper
© Georg Thieme Verlag Stuttgart · New York

Novel Type of α-Amino Acid Derived Imidazolium Ionic Liquids

Aleš Marek*
a   Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Pardubice, Studentská 573, Pardubice 532 10, Czech Republic
b   Institute of Organic Chemistry and Biochemistry Academy of Sciences of the Czech Republic, v.v.i., Flemingovo nám. 2, 16610 Prague 6, Czech Republic    Fax: +420(2)20183395   eMail: marek@uochb.cas.cz
,
Filip Bureš
a   Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Pardubice, Studentská 573, Pardubice 532 10, Czech Republic
,
Jiří Kulhánek
a   Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Pardubice, Studentská 573, Pardubice 532 10, Czech Republic
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Publikationsverlauf

Received: 14. April 2014

Accepted after revision: 30. Mai 2014

Publikationsdatum:
04. August 2014 (online)


Abstract

Four N-functionalized imidazole derivatives with α-amino acid residues were prepared and subsequently used for the construction of ten new optically pure imidazolium ionic liquids. The prepared imidazolium salts comprise three derivatives bearing one α-amino acid residue, five derivatives with two residues, and two derivatives possessing two bridged imidazolium ions. The molecular structure of one N-substituted imidazole was also confirmed by X-ray crystal structure analysis. Iodide and (di)bromide ions in five representative imidazolium salts were replaced with tetrafluoroborate ion in an attempt to lower the melting temperatures of these salts. In general, the properties of all target imidazolium ionic liquids could easily be tuned by N1/N3-substitution and the counterion used.

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