{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,4]],"date-time":"2026-04-04T18:36:17Z","timestamp":1775327777887,"version":"3.50.1"},"reference-count":43,"publisher":"Wiley","issue":"44","license":[{"start":{"date-parts":[[2014,7,17]],"date-time":"2014-07-17T00:00:00Z","timestamp":1405555200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"},{"start":{"date-parts":[[2014,7,17]],"date-time":"2014-07-17T00:00:00Z","timestamp":1405555200000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2014,10,27]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats: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.\u2005invicta and N.\u2005fulva. After being sprayed with alkaloid\u2010based S.\u2005invicta venom, N.\u2005fulva 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.\u2005invicta venom alkaloids. The resulting mixed\u2010cation ammonium formate milieu has properties consistent with its classification as a protic IL.<\/jats:p>","DOI":"10.1002\/anie.201404402","type":"journal-article","created":{"date-parts":[[2014,7,17]],"date-time":"2014-07-17T16:38:49Z","timestamp":1405615129000},"page":"11762-11765","source":"Crossref","is-referenced-by-count":32,"title":["On the Formation of a Protic Ionic Liquid in Nature"],"prefix":"10.1002","volume":"53","author":[{"given":"Li","family":"Chen","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Genevieve E.","family":"Mullen","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Myriam","family":"Le\u2005Roch","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Cody G.","family":"Cassity","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Nicolas","family":"Gouault","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Henry Y.","family":"Fadamiro","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Robert E.","family":"Barletta","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Richard A.","family":"O'Brien","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Richard E.","family":"Sykora","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Alexandra C.","family":"Stenson","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kevin N.","family":"West","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Howard E.","family":"Horne","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jeffrey M.","family":"Hendrich","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kang Rui","family":"Xiang","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"suffix":"Jr.","given":"James H.","family":"Davis","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2014,7,17]]},"reference":[{"key":"e_1_2_2_1_2","doi-asserted-by":"publisher","DOI":"10.1093\/ae\/43.1.23"},{"key":"e_1_2_2_2_2","doi-asserted-by":"publisher","DOI":"10.1371\/journal.pone.0045314"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1007\/s10530-013-0463-6"},{"key":"e_1_2_2_4_2","unstructured":"\u00a0"},{"key":"e_1_2_2_5_2","doi-asserted-by":"publisher","DOI":"10.1097\/ACI.0b013e328339f325"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.toxicon.2008.12.019"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.toxicon.2009.01.016"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1245833"},{"key":"e_1_2_2_9_2","doi-asserted-by":"crossref","first-page":"44","DOI":"10.1021\/cen-09209-scitech3","volume":"92","author":"Everts S.","year":"2014","journal-title":"Chem. Eng. News"},{"key":"e_1_2_2_10_2","unstructured":"\u00a0"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3gc41389f"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2cs35177c"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1017\/S0954102011000885"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1039\/C0CS00059K"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2gc35906e"},{"key":"e_1_2_2_16_2","unstructured":"G.\u2005J. Maximo R.\u2005J.\u2005B.\u2005N. Santos J.\u2005A. Lopes\u2010da\u2010Silva M.\u2005C. Costa A.\u2005J.\u2005A. Meirelles J.\u2005A.\u2005P. Coutinho ACS Sustainable Chem. Eng.\u00ad2014 DOI:."},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1097-4555(199904)30:4<325::AID-JRS371>3.0.CO;2-5"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1007\/s002140000187"},{"key":"e_1_2_2_19_2","unstructured":"\u201cRaman Spectral Studies of Solutions of Formic Acid and Methyl Formate\u201d: R.\u2005J. Bartholomew PhD Thesis University of Waterloo Ontario 1996."},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1071\/CH06363"},{"key":"e_1_2_2_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201209273"},{"key":"e_1_2_2_21_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201209273"},{"key":"e_1_2_2_22_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2ob25685a"},{"key":"e_1_2_2_23_2","first-page":"337","volume":"3","author":"Mirjafari A.","year":"2013","journal-title":"R. Soc. Chem. Adv."},{"key":"e_1_2_2_24_2","unstructured":"\u00a0"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200906169"},{"key":"e_1_2_2_25_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200906169"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2cc33609j"},{"key":"e_1_2_2_27_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2012.09.101"},{"key":"e_1_2_2_28_2","unstructured":"\u00a0"},{"key":"e_1_2_2_29_2","doi-asserted-by":"publisher","DOI":"10.1039\/b922524m"},{"key":"e_1_2_2_30_2","doi-asserted-by":"publisher","DOI":"10.1071\/CH06478"},{"key":"e_1_2_2_31_2","doi-asserted-by":"publisher","DOI":"10.1039\/b710014k"},{"key":"e_1_2_2_32_2","unstructured":"The direct sampling of the venom mix from the exoskeleton of an envenomatedN.\u2005fulvaimmediately after an ant\u2010to\u2010ant encounter is of keen interest to us but will be technically demanding to execute. Nevertheless attempts to do so are anticipated once regulatory issues bearing on such a study are addressed (a consequence of needing to employ a viableN.\u2005fulvapopulation in a locale where they have not yet established a presence in the wild)."},{"key":"e_1_2_2_33_2","unstructured":"For example see:"},{"key":"e_1_2_2_34_2","doi-asserted-by":"publisher","DOI":"10.1039\/c1cp21187k"},{"key":"e_1_2_2_35_2","first-page":"1383","volume":"39","author":"Petkovic M.","year":"2010","journal-title":"Chem. Soc. Rev."},{"key":"e_1_2_2_36_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3cp53395f"},{"key":"e_1_2_2_37_2","unstructured":"For example see:"},{"key":"e_1_2_2_38_2","doi-asserted-by":"publisher","DOI":"10.1071\/CH08441"},{"key":"e_1_2_2_39_2","doi-asserted-by":"publisher","DOI":"10.1039\/B618943A"},{"key":"e_1_2_2_40_2","doi-asserted-by":"publisher","DOI":"10.1039\/C1CP21947B"},{"key":"e_1_2_2_41_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2cp41625e"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201404402","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201404402","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.201404402","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201404402","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,3,8]],"date-time":"2026-03-08T17:43:47Z","timestamp":1772991827000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201404402"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2014,7,17]]},"references-count":43,"journal-issue":{"issue":"44","published-print":{"date-parts":[[2014,10,27]]}},"alternative-id":["10.1002\/anie.201404402"],"URL":"https:\/\/doi.org\/10.1002\/anie.201404402","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2014,7,17]]}}}