A ketenyl anion contains a C=C=O allene-like functional group, similar to ketene, with a negative charge on either terminal carbon or oxygen atom, forming resonance structures by moving a lone pair of electrons on C-C-O bond. Ketenes have been sources for many organic compounds with its reactivity despite a challenge to isolate them as crystal. Precedent method to obtain this product has been at gas phase or at reactive intermediate, and synthesis of ketene is used be done in extreme conditions (i.e., high temperature, low pressure).[1][2][3] Recently found stabilized ketenyl anions become easier to prepare compared to precedent synthetic procedure. A major feature about stabilized ketene is that it can be prepared from carbon monoxide (CO) reacting with main-group starting materials such as ylides, silylene, and phosphinidene to synthesize and isolate for further steps. As CO becomes a more common carbon source for various type of synthesis,[4] this recent finding about stabilizing ketene with main-group elements opens a variety of synthetic routes to target desired products.
^Robinson, Marin S.; Davico, Gustavo E.; Bierbaum, Veronica M.; DePuy, Charles H. (1994-10-06). "The gas phase ion/molecule chemistry of the carbon- 13 labeled ketenyl and methyl ketenyl anions with CS2, COS, and CO2". International Journal of Mass Spectrometry and Ion Processes. 137: 107–119. doi:10.1016/0168-1176(94)04030-3. ISSN 0168-1176.
^Allen, Annette D.; Tidwell, Thomas T. (2013-09-11). "Ketenes and Other Cumulenes as Reactive Intermediates". Chemical Reviews. 113 (9): 7287–7342. doi:10.1021/cr3005263. ISSN 0009-2665. PMID 23767795.
^Woodbury, Richard P.; Long, Nathan R.; Rathke, Michael W. (January 1978). "Reaction of trimethylsilylketene with strong base. Evidence for ketene enolate formation". The Journal of Organic Chemistry. 43 (2): 376. doi:10.1021/jo00396a057. ISSN 0022-3263.
^Fujimori, Shiori; Inoue, Shigeyoshi (2022-02-09). "Carbon Monoxide in Main-Group Chemistry". Journal of the American Chemical Society. 144 (5): 2034–2050. doi:10.1021/jacs.1c13152. ISSN 0002-7863. PMID 35068141. S2CID 246238305.
A ketenylanion contains a C=C=O allene-like functional group, similar to ketene, with a negative charge on either terminal carbon or oxygen atom, forming...
own in any of three forms: methanide anion (CH−3), methylium cation (CH+3) or methyl radical (CH• 3). The anion has eight valence electrons, the radical...
intermediate in the solution phase. The conjugate base, NO−, nitroxide anion, is the reduced form of nitric oxide (NO) and is isoelectronic with dioxygen...
occurs via [HONNO]− to nitrous oxide and the hydroxide anion. Hyponitrites (involving the N 2O2− 2 anion) are stable to reducing agents and more commonly act...
acetylene in a mole ratio of 100:1 In 2006 the negatively charged hexatriyne anion of this molecule, C6H−, was the first negatively charged ion to be discovered...
species in cell biology. The molecule has a bent structure. The superoxide anion, • O− 2, and the hydroperoxyl radical exist in equilibrium in aqueous solution:...
and occurs naturally, most notably in some ants. Esters, salts and the anion derived from formic acid are called formates. Industrially, formic acid...
Hence, MIISi with their zigzag chains of Si2− anions (containing two lone pairs of electrons on each Si anion that can accept protons) yield the polymeric...
tetrahedral structure and is isoelectronic with methane and the borohydride anion. In terms of size, the ammonium cation (rionic = 175 pm)[citation needed]...
leading to fulleride anions, [C60]n− (n = 1–6). The midpoint potentials of 1-electron reduction of buckminsterfullerene and its anions is given in the table...
acid (H−O−C≡N), and also of isofulminic acid (H−O−N+≡C−). Fulminate is the anion [C−≡N+−O−] or any of its salts. For historical reasons, the fulminate functional...
anions). This transfer of electrons is termed electrovalence in contrast to covalence. In the simplest case, the cation is a metal atom and the anion...
resulting in carbon monoxide poisoning. It is isoelectronic with both cyanide anion CN− and molecular nitrogen N2. Carbon monoxide is the simplest oxocarbon...
organic nitrile (hydrogen cyanide is a simpler nitrile, but the cyanide anion is not classed as organic). It is produced mainly as a byproduct of acrylonitrile...
white solid ionic compound consisting of sodium cations Na+ and hydroxide anions OH−. Sodium hydroxide is a highly corrosive base and alkali that decomposes...
one of the 3-positions. Reduction with sodium affords the radical anion. From this anion, a variety of pi-arene complexes can be prepared. Pyrene and its...
including tirapazamine, etravirine, revaprazan, and dasantafil. The cyanamide anion has the character of a pseudo chalcogen, cyanamide can therefore be regarded...
naphthalene forms the dark blue-green radical anion salts such as sodium naphthalene, Na+C10H− 8. The naphthalene anions are strong reducing agents. Naphthalene...
cyanol) (H−O−C≡N). The derived anion of isocyanic acid is the same as the derived anion of cyanic acid, and that anion is [N=C=O]−, which is called cyanate...
cannot be prepared in a condensed phase, as it would donate a proton to any anion, molecule or atom that it came in contact with. It has been shown to protonate...
The structure of solid NaCN is related to that of sodium chloride. The anions and cations are each six-coordinate. Potassium cyanide (KCN) adopts a similar...
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