On the Formation of a Protic Ionic Liquid in Nature

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. Verrückt nach ionischen Flüssigkeiten: In den USA konkurrieren die invasiven Ameisenarten S. invicta (Feuerameisen) and N. fulva (gelbbraune verückte Ameise) um Ressourcen. Während einer Konfrontation wird N. fulva von S. invicta mit einem lipophilen, piperidinbasierten Gift besprüht. N. fulva reagiert darauf mit der Absonderung ihres eigenen Giftes, der Ameisensäure. Die Kombination beider Gifte führt zur Bildung einer natürlichen protischen ionischen Flüssigkeit.