{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,12,15]],"date-time":"2025-12-15T14:10:03Z","timestamp":1765807803954,"version":"build-2065373602"},"reference-count":52,"publisher":"Wiley","issue":"4","license":[{"start":{"date-parts":[[2021,5,26]],"date-time":"2021-05-26T00:00:00Z","timestamp":1621987200000},"content-version":"am","delay-in-days":336,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#am"},{"start":{"date-parts":[[2020,6,24]],"date-time":"2020-06-24T00:00:00Z","timestamp":1592956800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100000923","name":"Australian Research Council","doi-asserted-by":"publisher","award":["DP180101187"],"award-info":[{"award-number":["DP180101187"]}],"id":[{"id":"10.13039\/501100000923","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["analyticalsciencejournals.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["J Mass Spectrom"],"published-print":{"date-parts":[[2021,4]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The gas\u2010phase extrusion\u2013insertion reactions of the copper complex [bathophenanthroline (Bphen)Cu<jats:sup>I<\/jats:sup>(O<jats:sub>2<\/jats:sub>CC<jats:sub>6<\/jats:sub>H<jats:sub>5<\/jats:sub>)]<jats:sup>2\u2212<\/jats:sup>, generated via electrospray ionization, was studied in a linear ion trap mass spectrometer with the combination of collision\u2010induced dissociation (CID) and ion\u2010molecule reaction (IMR) events. Multistage mass spectrometry (MS<jats:sup>n<\/jats:sup>) experiments and density functional theory (DFT) demonstrated that extrusion of carbon dioxide from [(Bphen)Cu(O<jats:sub>2<\/jats:sub>CC<jats:sub>6<\/jats:sub>H<jats:sub>5<\/jats:sub>)]<jats:sup>2\u2212<\/jats:sup> (CID) gives the organometallic intermediate [(Bphen)Cu(C<jats:sub>6<\/jats:sub>H<jats:sub>5<\/jats:sub>)]<jats:sup>2\u2212<\/jats:sup>, which subsequently reacts with carbon disulfide (IMR) via insertion to yield [(Bphen)Cu (SC(S)C<jats:sub>6<\/jats:sub>H<jats:sub>5<\/jats:sub>)]<jats:sup>2\u2212<\/jats:sup>. The fragmentation of the product ion resulted in the formation of [Bphen]<jats:sup>2\u2212<\/jats:sup>, [(Bphen)Cu]<jats:sup>\u2212<\/jats:sup> and C<jats:sub>6<\/jats:sub>H<jats:sub>5<\/jats:sub>CS<jats:sub>2<\/jats:sub><jats:sup>\u2212<\/jats:sup> under CID conditions. The formation of the latter two charge separation products thus provides evidence of C\u2013C bond formation in the IMR step. Although analogous studies with isocyanate, which is isoelectronic with CS<jats:sub>2<\/jats:sub>, showed a poor reactivity in the gas phase, the mechanistic understanding obtained from these model studies encourages future development of a solution phase protocol for the synthesis of amides from carboxylic acids and isocyanates mediated by copper(I) complexes.<\/jats:p>","DOI":"10.1002\/jms.4579","type":"journal-article","created":{"date-parts":[[2020,5,26]],"date-time":"2020-05-26T11:00:11Z","timestamp":1590490811000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["Gas\u2010phase studies of copper(I)\u2010mediated CO<sub>2<\/sub> extrusion followed by insertion of the heterocumulenes CS<sub>2<\/sub> or phenylisocyanate"],"prefix":"10.1002","volume":"56","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8443-9712","authenticated-orcid":false,"given":"Yang","family":"Yang","sequence":"first","affiliation":[{"name":"School of Chemistry, Bio21 Institute of Molecular Science and Biotechnology The University of Melbourne  Parkville Australia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Allan J.","family":"Canty","sequence":"additional","affiliation":[{"name":"School of Natural Sciences\u2014Chemistry University of Tasmania  Hobart Australia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8044-0502","authenticated-orcid":false,"given":"Richard A.J.","family":"O'Hair","sequence":"additional","affiliation":[{"name":"School of Chemistry, Bio21 Institute of Molecular Science and Biotechnology The University of Melbourne  Parkville Australia"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2020,6,24]]},"reference":[{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1351\/pac200880081725"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200704782"},{"key":"e_1_2_6_2_3","doi-asserted-by":"publisher","DOI":"10.1002\/ijch.201000039"},{"key":"e_1_2_6_2_4","doi-asserted-by":"publisher","DOI":"10.1021\/cr1002744"},{"key":"e_1_2_6_2_5","doi-asserted-by":"publisher","DOI":"10.1039\/c1cs15093f"},{"key":"e_1_2_6_2_6","doi-asserted-by":"publisher","DOI":"10.1007\/s11426-011-4381-0"},{"key":"e_1_2_6_2_7","doi-asserted-by":"publisher","DOI":"10.1055\/s-0031-1289686"},{"key":"e_1_2_6_2_8","doi-asserted-by":"publisher","DOI":"10.1039\/c2sc20312j"},{"key":"e_1_2_6_2_9","doi-asserted-by":"publisher","DOI":"10.1007\/978-3-642-34286-8"},{"key":"e_1_2_6_2_10","doi-asserted-by":"publisher","DOI":"10.1039\/c3ra41442f"},{"key":"e_1_2_6_2_11","doi-asserted-by":"publisher","DOI":"10.6023\/cjoc201805013"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.organomet.8b00720"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200604494"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar500377u"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/om501117p"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7CC00865A"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.organomet.8b00776"},{"key":"e_1_2_6_7_3","doi-asserted-by":"publisher","DOI":"10.1021\/acs.organomet.9b00820"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00713a047"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.9b04110"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5CC08367B"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1177\/1469066717729067"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1177\/1469066718795959"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1039\/b800371h"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4SC02151G"},{"key":"e_1_2_6_11_3","doi-asserted-by":"publisher","DOI":"10.1039\/c3dt32285h"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.1002\/cctc.201900346"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/om400358q"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/om500493w"},{"key":"e_1_2_6_13_3","doi-asserted-by":"publisher","DOI":"10.1021\/jo501886w"},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201102146"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2cp22970f"},{"volume-title":"Gaussian 09, Revision D.01","year":"2009","author":"Frisch MJ","key":"e_1_2_6_15_1"},{"key":"e_1_2_6_16_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00214-007-0310-x"},{"key":"e_1_2_6_17_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.452288"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1007\/BF01114537"},{"key":"e_1_2_6_18_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF00533485"},{"key":"e_1_2_6_19_1","doi-asserted-by":"publisher","DOI":"10.1021\/j100717a029"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar00072a001"},{"key":"e_1_2_6_20_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.1627293"},{"key":"e_1_2_6_21_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp9716997"},{"key":"e_1_2_6_22_1","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1096-9888(199705)32:5<461::AID-JMS515>3.0.CO;2-H"},{"key":"e_1_2_6_23_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6CP00494F"},{"key":"e_1_2_6_24_1","doi-asserted-by":"publisher","DOI":"10.1016\/0039-9140(61)80006-4"},{"key":"e_1_2_6_25_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF02990349"},{"key":"e_1_2_6_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.inorgchem.8b01529"},{"key":"e_1_2_6_27_1","doi-asserted-by":"publisher","DOI":"10.1039\/c1dt10771b"},{"key":"e_1_2_6_28_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-328X(00)83052-1"},{"key":"e_1_2_6_29_1","doi-asserted-by":"publisher","DOI":"10.1107\/S1600536801018281"},{"key":"e_1_2_6_30_1","doi-asserted-by":"publisher","DOI":"10.1021\/om300683c"},{"key":"e_1_2_6_31_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja973814x"},{"key":"e_1_2_6_32_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0020-1693(00)84827-6"}],"container-title":["Journal of Mass Spectrometry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fjms.4579","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/jms.4579","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/jms.4579","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/am-pdf\/10.1002\/jms.4579","content-type":"application\/pdf","content-version":"am","intended-application":"syndication"},{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/jms.4579","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,16]],"date-time":"2025-10-16T16:42:54Z","timestamp":1760632974000},"score":1,"resource":{"primary":{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/10.1002\/jms.4579"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,6,24]]},"references-count":52,"journal-issue":{"issue":"4","published-print":{"date-parts":[[2021,4]]}},"alternative-id":["10.1002\/jms.4579"],"URL":"https:\/\/doi.org\/10.1002\/jms.4579","archive":["Portico"],"relation":{},"ISSN":["1076-5174","1096-9888"],"issn-type":[{"type":"print","value":"1076-5174"},{"type":"electronic","value":"1096-9888"}],"subject":[],"published":{"date-parts":[[2020,6,24]]},"assertion":[{"value":"2020-04-16","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2020-05-20","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2020-06-24","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e4579"}}