193:
35:
26:
329:
590:
at low temperature. Potassium acetylenediolate is a pale yellow solid that reacts explosively with air, halogens, halogenated hydrocarbons, alcohols, water, and any substance which possesses an acidic hydrogen.
775:
Wang, Jia; Turner, Andrew M.; Marks, Joshua H.; Zhang, Chaojiang; Kleimeier, N. Fabian; Bergantini, Alexandre; Singh, Santosh K.; Fortenberry, Ryan C.; Kaiser, Ralf I. (1 June 2024).
342:
981:
242:
881:
Zur
Kenntnis der sogenannten Alkalicarbonyle. II. Die Kristallstrukturen des Rubidium- und Caesium-acetylendiolats, RbOC≡CORb und CsOC≡COCs.
496:; but for a long time the product was assumed to be "potassium carbonyl" (KCO). Over the next 130 years were described the "carbonyls" of
841:
Zur
Kenntnis der sogenannten «Alkalicarbonyle» IV Über die Reaktion von geschmolzenem Kalium mit Kohlenmonoxid. Helvetica Chimica Acta
34:
207:
903:. Thesis, Pennsylvania State University; also Technical Memo A642321, Penn State University Park Applied Research Lab. 227 pages.
807:
Justus Liebig (1834), Annalen der Chemie und
Pharmacie, volume 11, p. 182. Cited by Raymond N. Vrtis et al. (1988), JACS p. 7564.
604:
432:
934:
Mechanistic
Studies on the Reductive Cyclooligomerisation of CO by U(III) Mixed Sandwich Complexes; the Molecular Structure of
914:
Synthesis and
Stabilization of Tantalum-Coordinated Dihydroxyacetylene from Two Reductively Coupled Carbon Monoxide Ligands
706:
349:
25:
748:
Maier, Günther; Rohr, Christine (1995). "Ethynediol: Photochemical generation and matrix-spectroscopic identification".
586:
Acetylenediolates can also be prepared by the rapid reaction of CO and a solution of the corresponding metal in liquid
171:
777:"Preparation of Acetylenediol (HOCCOH) and Glyoxal (HCOCHO) in Interstellar Analog Ices of Carbon Monoxide and Water"
671:
419:
at 10 K (−263 °C). Recently, this molecule was synthesized in interstellar ice analogs composed of
659:
449:
431:
O) upon exposure to energetic electrons and detected upon sublimation by isomer-selective photoionization
861:
Zur
Kenntnis der sogenannten «Alkalicarbonyle» I Die Kristallstruktur des Kalium-acetylendiolats, KOC≡COK
600:
520:(Pearson, 1933). The reaction was eventually shown to yield a mixture of the potassium acetylenediolate
658:
have been obtained from carbon monoxide under mild conditions by reductive coupling of CO ligands in
188:
47:
468:) dianion O−C≡C−O are known. They are not however prepared from ethynediol, but by the reduction of
73:
369:
107:
971:
485:
408:
404:
134:
949:
917:
884:
864:
844:
824:
788:
757:
416:
270:
83:
489:
469:
420:
114:
883:
Zeitschrift für anorganische und allgemeine Chemie, Volume 330 Issue 5-6, Pages 251–258.
192:
976:
702:
320:
965:
308:
948:
Journal of the
American Chemical Society, volume 130, issue 42, pages 13816–13817.
159:
412:
611:
385:
912:
Raymond N. Vrtis, Ch. Pulla Rao, Simon G. Bott, and
Stephen J. Lippard (1988),
793:
776:
761:
583:
The structure of these salts was clarified only in 1963 by Büchner and Weiss.
298:
125:
888:
868:
848:
505:
493:
381:
701:
Terlouw, Johan K.; Burgers, Peter C.; van Baar, Ben L. M.; Weiske, Thomas;
635:
513:
921:
676:
587:
517:
509:
388:
146:
953:
719:
N–CC–OH and
Related Compounds by Selective Reduction of Their Cations"
828:
501:
497:
319:
Except where otherwise noted, data are given for materials in their
932:
Alistair S. Frey, F. Geoffrey N. Cloke, Peter B. Hitchcock (2008),
424:
384:. Acetylenediol is unstable in the condensed phase, although its
113:
106:
96:
681:
377:
373:
863:. Helvetica Chimica Acta, Volume 46 Issue 4, Pages 1121–1127.
176:
901:
The
Chemical Behavior of the Alkali Metal Acetylenediolates
448:
Like the diol, most simple ether derivatives are labile.
916:
J. Am. Chem. Soc., volume 110 issue 22, pp. 7564–7566.
337:
823:. Nature, volume 131, pp. 166–167 (4 February 1933).
403:
Acetylenediol was first observed in the gas-phase by
158:
82:
707:"The Formation in the Gas Phase of HO–CC–OH, H
8:
610:Acetylenediolate and related anions such as
433:reflectron time-of-flight mass spectrometry
821:Carbonyls of Lithium, Rubidium and Caesium
191:
133:
17:
815:
813:
792:
693:
247:
212:
187:
982:Organic compounds with 2 carbon atoms
843:, Volume 47 Issue 6, Pages 1415–1423.
407:. The compound was later obtained by
219:Key: ZUQAPLKKNAQJAU-UHFFFAOYSA-N
7:
229:Key: ZUQAPLKKNAQJAU-UHFFFAOYAS
149:
14:
879:E. Weiss, Werner Büchner (1963),
452:is however a distillable liquid.
859:Werner Büchner, E. Weiss (1963)
839:Werner Büchner, E. Weiss (1964)
472:. Potassium acetylenediolate (K
327:
282:
33:
24:
899:Charles Kenneth Taylor (1982),
323:(at 25 °C , 100 kPa).
550:and potassium benzenehexolate
488:in 1834, from the reaction of
288:
276:
216:InChI=1S/C2H2O2/c3-1-2-4/h3-4H
1:
226:InChI=1/C2H2O2/c3-1-2-4/h3-4H
605:bis(dimethylphosphino)ethane
603:, such as Cl where dmpe is
372:with formula HO−C≡C−OH (an
998:
672:Acetylenedicarboxylic acid
504:(Gunz and Mentrel, 1903),
781:The Astrophysical Journal
762:10.1002/jlac.199619960303
317:
303:58.07 g/mol
263:
238:
203:
66:
58:
46:
41:
32:
23:
889:10.1002/zaac.19643300504
869:10.1002/hlca.19630460404
849:10.1002/hlca.19640470604
794:10.3847/1538-4357/ad3c3e
484:) was first obtained by
660:organouranium complexes
599:Acetylenediol can form
450:Di-tert-butoxyacetylene
819:T. G. Pearson (1933),
601:coordination compounds
595:Coordination complexes
508:(Roederer, 1906), and
456:Acetylenediolate salts
444:Alkoxide derivatives
48:Preferred IUPAC name
922:10.1021/ja00230a062
20:
500:(Johannis, 1893),
417:solid argon matrix
370:chemical substance
350:Infobox references
61:Dihydroxyacetylene
18:
954:10.1021/ja8059792
405:mass spectrometry
358:Chemical compound
356:
355:
172:CompTox Dashboard
115:Interactive image
108:Interactive image
989:
956:
930:
924:
910:
904:
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829:10.1038/131166b0
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462:acetylenediolate
340:
334:
331:
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290:
284:
278:
271:Chemical formula
196:
195:
180:
178:
162:
151:
137:
117:
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86:
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28:
21:
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750:Liebigs Annalen
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703:Schwarz, Helmut
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490:carbon monoxide
483:
479:
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470:carbon monoxide
458:
446:
441:
430:
421:carbon monoxide
401:
395:is well known.
394:
359:
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189:DTXSID601028556
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756:(3): 307–309.
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492:with metallic
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376:). It is the
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321:standard state
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29:
19:Acetylenediol
13:
10:
9:
6:
4:
3:
2:
994:
983:
980:
978:
975:
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584:
581:
519:
515:
511:
507:
503:
499:
495:
491:
487:
471:
467:
466:ethynediolate
463:
460:Salts of the
455:
453:
451:
443:
438:
436:
434:
426:
422:
418:
414:
410:
406:
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371:
367:
363:
362:Acetylenediol
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309:Boiling point
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22:
16:
933:
928:
913:
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835:
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753:
749:
743:
731:. Retrieved
726:
722:
696:
609:
598:
585:
582:
465:
461:
459:
447:
413:squaric acid
402:
365:
361:
360:
67:Identifiers
59:Other names
15:
439:Derivatives
313:decomposes
264:Properties
966:Categories
688:References
409:photolysis
366:ethynediol
299:Molar mass
126:ChemSpider
95:3D model (
84:16005-17-7
74:CAS Number
52:Ethynediol
787:(2): 79.
729:: 357–359
506:strontium
494:potassium
423:(CO) and
399:Detection
382:acetylene
972:Alkynols
938:(μ-η:η-C
733:1 August
705:(1986).
666:See also
636:squarate
514:rubidium
386:tautomer
711:N–CC–NH
677:Ethynol
612:deltate
588:ammonia
518:caesium
510:lithium
389:glyoxal
368:, is a
343:what is
341: (
250:C(#CO)O
160:9942115
147:PubChem
135:8117727
723:CHIMIA
516:, and
502:barium
498:sodium
486:Liebig
338:verify
335:
243:SMILES
42:Names
977:Diols
425:water
415:in a
391:(CHO)
364:, or
255:OC#CO
208:InChI
97:JSmol
754:1996
735:2009
682:Ynol
634:and
378:diol
374:ynol
950:doi
918:doi
885:doi
865:doi
845:doi
825:doi
789:doi
785:967
758:doi
715:, H
411:of
380:of
177:EPA
150:CID
968::
812:^
783:.
779:.
752:.
727:40
725:.
721:.
662:.
607:.
580:.
512:,
435:.
427:(H
952::
946:)
944:2
942:O
940:2
936:2
920::
887::
867::
847::
827::
797:.
791::
764:.
760::
737:.
717:2
713:2
709:2
653:4
648:O
644:4
639:C
629:3
624:O
620:3
615:C
575:6
570:O
566:6
561:C
557:6
552:K
545:2
540:O
536:2
531:C
527:2
522:K
482:2
480:O
478:2
476:C
474:2
464:(
429:2
393:2
333:N
292:2
289:O
286:2
283:H
280:2
277:C
179:)
175:(
99:)
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