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40:
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27:
535:
Raamat, E.; Kaupmees, K.; Ovsjannikov, G.; Trummal, A.; Kütt, A.; Saame, J.; Koppel, I.; Kaljurand, I.; Lipping, L.; Rodima, T.; Pihl, V.; Koppel, I. A.; Leito, I. (2013). "Acidities of strong neutral Brønsted acids in different media".
496:. The team discovered that cyanoform was stable at temperatures below −40°C; previous beliefs were that cyanoform was stable at room temperature. The isolation confirmed that cyanoform is a colorless liquid.
421:
255:
665:
391:
Dilute solutions of this acid, as well as its salts, have long been well known. Cyanoform ranks as one of the most acidic of the
424:
in water (a reaction first tried by H. Schmidtmann in 1896 with inconclusive results) is reported to result in the formation of
597:Šišak, Dubravka; McCusker, Lynne B.; Buckl, Andrea; Wuitschik, Georg; Wu, Yi-Lin; Schweizer, W. Bernd; Dunitz, Jack D. (2010).
220:
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638:
655:
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67:
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620:
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379:. For many years, chemists have been unable to isolate this compound as a neat, free
172:
610:
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545:
519:
358:
354:
278:
488:
In
September 2015 cyanoform was successfully isolated by a team of scientists at
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649:
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624:
615:
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523:
413:
39:
383:. However, in September 2015, reports surfaced of a successful isolation.
511:
Soltner, T.; Häusler J.; Kornath A.J. "The
Existence of Tricyanomethane"
392:
376:
368:
295:
138:
48:
549:
425:
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Except where otherwise noted, data are given for materials in their
477:
26:
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https://www.sciencenews.org/article/elusive-acid-finally-created
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464:
is reported to yield 1-chloro-1-amino-2,2-dicyanoethylene (
380:
461:
456:, depending on the precise conditions. The reaction of
321:−40 °C (−40 °F; 233 K) (decomposes)
647:
171:
460:gas with sodium tricyanomethanide dissolved in
102:
572:Berichte der deutschen chemischen Gesellschaft
599:"The Search for Tricyanomethane (Cyanoform)"
562:
204:
146:
614:
16:Cyanocarbon compound derived from methane
637:Mole, B - Elusive acid finally created
565:"Ueber einige Derivate des Malonitrils"
513:Angewandte Chemie International Edition
444:)-3-amino-2-cyano-3-hydroxyacrylamide,
200:
648:
232:Key: HFWIMJHBCIGYFH-UHFFFAOYSA-N
367:. It is a colorless liquid. It is a
242:Key: HFWIMJHBCIGYFH-UHFFFAOYAU
162:
13:
666:Substances discovered in the 2010s
47:
38:
14:
677:
229:InChI=1S/C4HN3/c5-1-4(2-6)3-7/h4H
239:InChI=1/C4HN3/c5-1-4(2-6)3-7/h4H
25:
405:of -5.1 in water and measured p
331:(at 25 °C , 100 kPa).
631:
590:
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1:
603:Chemistry: A European Journal
499:
386:
490:Ludwig Maximilian University
483:
7:
450:N−)(HO−)C=C(−C≡N)(−C(=O)−NH
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10:
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584:10.1002/cber.18960290204
563:Schmidtmann, H. (1896).
422:sodium tricyanomethanide
616:10.1002/chem.201000559
524:10.1002/anie.201506753
72:Methanetricarbonitrile
52:
43:
440:or the formation of (
51:
42:
68:Preferred IUPAC name
303: g·mol
21:
538:J. Phys. Org. Chem
428:tricyanomethanide
416:. The reaction of
395:with an estimated
371:and derivative of
335:Infobox references
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19:
343:Chemical compound
341:
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311:Colorless liquid
185:CompTox Dashboard
128:Interactive image
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578:(2): 1168–1175.
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550:10.1002/poc.2946
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359:chemical formula
355:organic compound
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279:Chemical formula
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609:(24): 7224–30.
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351:tricyanomethane
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81:Tricyanomethane
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544:(2): 162–170.
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329:standard state
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263:C(#N)C(C#N)C#N
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656:Organic acids
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418:sulfuric acid
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317:Boiling point
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434:O][C(CN)
414:acetonitrile
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398:
393:carbon acids
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377:cyano groups
350:
346:
345:
87:Identifiers
79:Other names
375:with three
369:cyanocarbon
308:Appearance
272:Properties
650:Categories
500:References
476:) and its
412:of 5.1 in
387:Properties
296:Molar mass
139:ChemSpider
115:3D model (
94:CAS Number
20:Cyanoform
484:Isolation
426:hydronium
357:with the
347:Cyanoform
661:Nitriles
625:20480465
478:tautomer
353:) is an
104:454-50-2
470:C=C(−NH
373:methane
290:
173:5232958
160:PubChem
148:4402366
623:
494:Munich
466:(N≡C−)
430:[H
362:HC(CN)
301:91.073
285:HC(CN)
256:SMILES
62:Names
568:(PDF)
420:with
221:InChI
117:JSmol
621:PMID
516:2015
381:acid
611:doi
580:doi
546:doi
520:doi
492:of
474:)Cl
462:THF
458:HCl
190:EPA
163:CID
652::
619:.
607:16
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446:(H
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472:2
468:2
454:)
452:2
448:2
442:Z
438:]
436:3
432:3
410:a
407:K
402:a
399:K
397:p
364:3
349:(
287:3
192:)
188:(
119:)
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