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On the Formation of a Protic Ionic Liquid in Nature
Author(s) -
Chen Li,
Mullen Genevieve E.,
Le Roch Myriam,
Cassity Cody G.,
Gouault Nicolas,
Fadamiro Henry Y.,
Barletta Robert E.,
O'Brien Richard A.,
Sykora Richard E.,
Stenson Alexandra C.,
West Kevin N.,
Horne Howard E.,
Hendrich Jeffrey M.,
Xiang Kang Rui,
Davis James H.
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201404402
Subject(s) - formic acid , ammonium formate , venom , protonation , chemistry , ionic liquid , ammonium , formate , alkaloid , organic chemistry , ion , biochemistry , catalysis
The practical utility of ionic liquids (ILs) makes the absence (heretofore) of reported examples from nature quite puzzling, given the facility with which nature produces many other types of exotic but utilitarian substances. In that vein, we report here the identification and characterization of a naturally occurring protic IL. It can be formed during confrontations between the ants S. invicta and N. fulva. After being sprayed with alkaloid‐based S. invicta venom, N. fulva detoxifies by grooming with its own venom, formic acid. The mixture is a viscous liquid manifestly different from either of the constituents. Further, we find that the change results as a consequence of formic acid protonation of the N centers of the S. invicta venom alkaloids. The resulting mixed‐cation ammonium formate milieu has properties consistent with its classification as a protic IL.