On the Formation of a Protic Ionic Liquid in Nature1. Issue 44 (17th July 2014)

• Record Type: Journal Article
• Authors: 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.
• Is Part Of: Angewandte Chemie international edition. Volume 53:Issue 44(2014)
• Page Start: 11762
• Page End: 11765
• Publication Date: 2014-07-17
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201404402
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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.</p> </abstract>