Acetylenedicarboxylate

Acetylenedicarboxylate (often abbreviated as ADC or adc) is a divalent anion with formula C4O42− or [O2C–C≡C–CO2]2−; or any salt or ester thereof. The anion can be derived from acetylenedicarboxylic acid C4H2O4 by the loss of two protons. It is one of several oxocarbon anions which, like carbonate CO32− and oxalate C2O42−, consist solely of carbon and oxygen.

Removal of a single proton from the acid gives the monovalent hydrogenacetylenedicarboxylate anion, HC4O4−.

Synthesis and reactions

The salt potassium acetylenedicarboxylate K2C4O4 is an intermediate in the standard synthesis route of the acid.[1] Both compounds were obtained by E. Bandrowski in 1877.[2][3]

The ADC anion can at as a ligand in organometallic complexes, e.g. the blue polymeric complex with copper(II) and 2,2'-bipyridine, [Cu2+ · C4O42− · (C5H4N)2]n.[4][5]

Thallium acetylenedicarboxylate Tl2C4O4 decomposes at 195 °C leaving a residue of pyrophoric thallium powder.[6]

See also

References

  1. ^ Abbott, T. W.; Arnold, R. T.; Thompson, R. B., "Acetylenedicarboxylic acid", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv2p0010 ; Coll. Vol. 2: 10 
  2. ^ E. Bandrowski (1877) Ueber Acetylendicarbonsäure Chemische Berichte band 10, 838–842 (1877).
  3. ^ E. Bandrowski (1879) Weitere Beiträge zur Kenntniss der Acetylendicarbonsäure. Berichte der deutschen chemischen Gesellschaft, volume 12, issue 2, 2212–2216. doi:10.1002/cber.187901202261
  4. ^ Ming Xing LI, Min SHAO, Hui DAI, Bao Li AN, Wen Cong LU, Yu ZHU, Chen Xia DU (2005), Synthesis and Crystal Structure of a Novel Copper (II) Complex with Acetylenedicarboxylate and 2,2'-Bipyridine. Chinese Chemical Letters, volume 16, issue 10, pp. 1405–1408.
  5. ^ Min Shao, Ming-Xing Li, Hui Dai, Wen-Cong Lu and Bao-Li An (2007), Polynuclear complexes incorporating Cu(II) and Mn(II) centers bridged by acetylenedicarboxylate: Structure, thermal stability and magnetism. Journal of Molecular Structure, volume 829, issues 1–3, pp. 155–160.
  6. ^ Ruth Ahlers and Uwe Ruschewitz (2009), Non-centrosymmetric coordination polymers based on thallium and acetylenedicarboxylate. Solid State Sciences, volume 11, issue 6, pp. 1058–1064.