title: On the formation of a protic ionic liquid in nature.
abstract: 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.
authors.affiliation: State Key Lab of Integrated Management of Pest Insects and Rodents; Institute of Zoology, Chinese Academy of Sciences, Beijing, 100101 (P.R. China).
authors.forename: Li
authors.initials: L
authors.lastname: Chen
authors.forename: Genevieve E
authors.initials: GE
authors.lastname: Mullen
authors.forename: Myriam
authors.initials: M
authors.lastname: Le Roch
authors.forename: Cody G
authors.initials: CG
authors.lastname: Cassity
authors.forename: Nicolas
authors.initials: N
authors.lastname: Gouault
authors.forename: Henry Y
authors.initials: HY
authors.lastname: Fadamiro
authors.forename: Robert E
authors.initials: RE
authors.lastname: Barletta
authors.forename: Richard A
authors.initials: RA
authors.lastname: O'Brien
authors.forename: Richard E
authors.initials: RE
authors.lastname: Sykora
authors.forename: Alexandra C
authors.initials: AC
authors.lastname: Stenson
authors.forename: Kevin N
authors.initials: KN
authors.lastname: West
authors.forename: Howard E
authors.initials: HE
authors.lastname: Horne
authors.forename: Jeffrey M
authors.initials: JM
authors.lastname: Hendrich
authors.forename: Kang Rui
authors.initials: KR
authors.lastname: Xiang
authors.forename: James H
authors.initials: JH
authors.lastname: Davis
mesh_terms: D000818:Animals; D001000:Ants; D052578:Ionic Liquids / Q000378:metabolism*
chemical_list: D052578:Ionic Liquids
keywords: alkaloids; ionic liquid; natural products; solenopsin; venom