{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,17]],"date-time":"2026-01-17T04:49:19Z","timestamp":1768625359806,"version":"3.49.0"},"reference-count":42,"publisher":"Wiley","issue":"32","license":[{"start":{"date-parts":[[2017,6,22]],"date-time":"2017-06-22T00:00:00Z","timestamp":1498089600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001655","name":"Deutscher Akademischer Austauschdienst","doi-asserted-by":"publisher","award":["10.13039\/501100001655"],"award-info":[{"award-number":["10.13039\/501100001655"]}],"id":[{"id":"10.13039\/501100001655","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2017,8]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Solutions of azidomethylidenemalononitrile were photolyzed at low temperatures to produce the corresponding 2H\u2010azirine and tricyanomethane, which were analyzed by low\u2010temperature NMR spectroscopy. The latter product was also observed after short thermolysis of the azide precursor in solution whereas irradiation of the azide isolated in an argon matrix did not lead to tricyanomethane, but to unequivocal detection of the tautomeric ketenimine by IR spectroscopy for the first time. When the long\u2010known \u201caquoethereal\u201d greenish phase generated from potassium tricyanomethanide, dilute sulfuric acid, and diethyl ether was rapidly evaporated and sublimed, a mixture of hydronium tricyanomethanide and tricyanomethane was formed instead of the previously claimed ketenimine tautomer. Under special conditions of sublimation, single crystals of tricyanomethane could be isolated, which enabled the analysis of the molecular structure by X\u2010ray diffraction.<\/jats:p>","DOI":"10.1002\/anie.201704561","type":"journal-article","created":{"date-parts":[[2017,5,16]],"date-time":"2017-05-16T13:51:00Z","timestamp":1494942660000},"page":"9582-9586","source":"Crossref","is-referenced-by-count":23,"title":["Tricyanomethane and Its Ketenimine Tautomer: Generation from Different Precursors and Analysis in Solution, Argon Matrix, and as a Single Crystal"],"prefix":"10.1002","volume":"56","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-2335-7523","authenticated-orcid":false,"given":"Klaus","family":"Banert","sequence":"first","affiliation":[{"name":"Chemnitz University of Technology Organic Chemistry  Strasse der Nationen 62 09111 Chemnitz Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Madhu","family":"Chityala","sequence":"additional","affiliation":[{"name":"Chemnitz University of Technology Organic Chemistry  Strasse der Nationen 62 09111 Chemnitz Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Manfred","family":"Hagedorn","sequence":"additional","affiliation":[{"name":"Chemnitz University of Technology Organic Chemistry  Strasse der Nationen 62 09111 Chemnitz Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Helmut","family":"Beckers","sequence":"additional","affiliation":[{"name":"Institut f\u00fcr Chemie und Biochemie Anorganische Chemie Freie Universit\u00e4t Berlin  Fabeckstrasse 34\u201336 14195 Berlin Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Tony","family":"St\u00fcker","sequence":"additional","affiliation":[{"name":"Institut f\u00fcr Chemie und Biochemie Anorganische Chemie Freie Universit\u00e4t Berlin  Fabeckstrasse 34\u201336 14195 Berlin Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sebastian","family":"Riedel","sequence":"additional","affiliation":[{"name":"Institut f\u00fcr Chemie und Biochemie Anorganische Chemie Freie Universit\u00e4t Berlin  Fabeckstrasse 34\u201336 14195 Berlin Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Tobias","family":"R\u00fcffer","sequence":"additional","affiliation":[{"name":"Chemnitz University of Technology Inorganic Chemistry  Strasse der Nationen 62 09111 Chemnitz Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Heinrich","family":"Lang","sequence":"additional","affiliation":[{"name":"Chemnitz University of Technology Inorganic Chemistry  Strasse der Nationen 62 09111 Chemnitz Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2017,6,22]]},"reference":[{"key":"e_1_2_2_1_1","doi-asserted-by":"publisher","DOI":"10.1002\/cber.18960290204"},{"key":"e_1_2_2_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/cber.18990320193"},{"key":"e_1_2_2_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo01036a503"},{"key":"e_1_2_2_4_1","unstructured":"For a more detailed description of the cyanoform story see the excellent introduction in Ref.\u2009[5]."},{"key":"e_1_2_2_5_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201000559"},{"key":"e_1_2_2_6_1","doi-asserted-by":"publisher","DOI":"10.1016\/0022-2860(77)87015-4"},{"key":"e_1_2_2_7_1","doi-asserted-by":"publisher","DOI":"10.1515\/znb-1987-0311"},{"key":"e_1_2_2_8_1","unstructured":"\u00a0"},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/j100798a004"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/poc.2946"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo101409p"},{"key":"e_1_2_2_12_1","unstructured":"\u00a0"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jpca.6b10951"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200800583"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1016\/0022-2860(75)87072-4"},{"key":"e_1_2_2_16_2","first-page":"155","volume":"13","author":"Stoyanov S. 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Khim."},{"key":"e_1_2_2_23_1","unstructured":"For an investigation of8by quantum-chemical methods see Ref.\u2005[9a]."},{"key":"e_1_2_2_24_1","unstructured":"For details see the Supporting Information."},{"key":"e_1_2_2_25_1","unstructured":"For the chemistry of vinyl azides see:"},{"key":"e_1_2_2_26_2","first-page":"115","volume-title":"Organic Azides, Syntheses and Applications","author":"Banert K.","year":"2010"},{"key":"e_1_2_2_27_2","first-page":"541","volume-title":"Science of Synthesis, Vol.\u200533","author":"Collier S. 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