Glyoxylide
   HOME

TheInfoList



OR:

Ethylene dione or ethylenedione, also called dicarbon dioxide, Carbon peroxide, ethenedione, or ethene-1,2-dione, is a
chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...
with the
formula In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwe ...
or . It is an
oxide An oxide () is a chemical compound containing at least one oxygen atom and one other element in its chemical formula. "Oxide" itself is the dianion (anion bearing a net charge of −2) of oxygen, an O2− ion with oxygen in the oxidation st ...
of
carbon Carbon () is a chemical element; it has chemical symbol, symbol C and atomic number 6. It is nonmetallic and tetravalence, tetravalent—meaning that its atoms are able to form up to four covalent bonds due to its valence shell exhibiting 4 ...
(an
oxocarbon In chemistry, an oxocarbon or oxide of carbon is a chemical compound consisting only of carbon and oxygen. The simplest and most common oxocarbons are carbon monoxide (CO) and carbon dioxide (). Many other stable (practically if not thermodynamica ...
), and can be described as the carbon-carbon covalent
dimer Dimer may refer to: * Dimer (chemistry), a chemical structure formed from two similar sub-units ** Protein dimer, a protein quaternary structure ** d-dimer ** TH-dimer * Dimer model, an item in statistical mechanics, based on ''domino tiling'' * ...
of
carbon monoxide Carbon monoxide (chemical formula CO) is a poisonous, flammable gas that is colorless, odorless, tasteless, and slightly less dense than air. Carbon monoxide consists of one carbon atom and one oxygen atom connected by a triple bond. It is the si ...
. It can also be thought of as the
dehydrated In physiology, dehydration is a lack of total body water that disrupts Metabolism, metabolic processes. It occurs when free water loss exceeds intake, often resulting from excessive sweating, health conditions, or inadequate consumption of wate ...
form of
glyoxylic acid Glyoxylic acid or oxoacetic acid is an organic compound. Together with acetic acid, glycolic acid, and oxalic acid, glyoxylic acid is one of the C2 carboxylic acids. It is a colourless solid that occurs naturally and is useful industrially. Str ...
(), or a
ketone In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone ( ...
of
ethenone Ethenone is the formal name for ketene, an organic compound with formula or . It is the simplest member of the ketene class. It is an important reagent for acetylations. Properties Ethenone is a highly reactive gas (at Standard temperature an ...
.


Synthesis attempts

The existence of ethylenedione was first suggested in 1913.H. Staudinger, E. Anthes, ''Ber. Dtsch. Chem. Ges.'' 1913, 46, 1426. However, for over a century the compound had eluded all attempts to synthesize and observe it, and it came to be considered a purely
hypothetical compound A hypothetical chemical compound is a chemical compound that has been conceived of, but is not known to have been synthesized, observed, or isolated (identified or shown to exist). Some hypothetical compounds cannot form at all, due to steric ef ...
, or at best an "exceedingly coy molecule". In 2015, a research group reported the creation of ethylenedione — by using
laser A laser is a device that emits light through a process of optical amplification based on the stimulated emission of electromagnetic radiation. The word ''laser'' originated as an acronym for light amplification by stimulated emission of radi ...
light to eject an
electron The electron (, or in nuclear reactions) is a subatomic particle with a negative one elementary charge, elementary electric charge. It is a fundamental particle that comprises the ordinary matter that makes up the universe, along with up qua ...
from the corresponding stable singly-charged
anion An ion () is an atom or molecule with a net electrical charge. The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by conven ...
— and its spectroscopic characterization. However, the reported spectrum was later found to match that of the oxyallyl diradical, , formed by rearrangement or disproportionation under the high-energy experimental conditions rather than simple electron loss.Katharine G. Lunny, Yanice Benitez, Yishai Albeck, Daniel Strasser, John F. Stanton, Robert E. Continetti (2018): "Spectroscopy of Ethylenedione and Ethynediolide: A Reinvestigation". ''Angewandte Chemie, International Edition'', volume 57, issue 19, pages 5394-5397.


Theoretical investigations

Despite the existence of the
closed-shell In atomic physics and quantum chemistry, the electron configuration is the distribution of electrons of an atom or molecule (or other physical structure) in atomic or molecular orbitals. For example, the electron configuration of the neon atom ...
Kekulé structure, O=C=C=O, the lowest bound state of ethyledione is a triplet. It would then be a
diradical In chemistry, a diradical is a chemical species, molecular species with two electrons occupying molecular orbitals (MOs) which are degenerate energy level, degenerate. The term "diradical" is mainly used to describe organic compounds, where most ...
, with an
electronic structure Quantum chemistry, also called molecular quantum mechanics, is a branch of physical chemistry focused on the application of quantum mechanics to chemical systems, particularly towards the quantum-mechanical calculation of electronic contributions ...
motif similar to the
oxygen Oxygen is a chemical element; it has chemical symbol, symbol O and atomic number 8. It is a member of the chalcogen group (periodic table), group in the periodic table, a highly reactivity (chemistry), reactive nonmetal (chemistry), non ...
molecule. However, when the molecule is distorted away from its equilibrium geometry, the potential surfaces of the triplet and
singlet state In quantum mechanics, a singlet state usually refers to a system in which all electrons are paired. The term 'singlet' originally meant a linked set of particles whose net angular momentum is zero, that is, whose overall spin quantum number s=0. A ...
s intersect, allowing for
intersystem crossing Intersystem crossing (ISC) is an isoenergetic radiationless process involving a transition between the two electronic states with different spin multiplicity. Excited singlet and triplet states When an electron in a molecule with a singlet grou ...
to the singlet state, which is unbound and dissociates to two ground-state CO molecules. The timescale of the intersystem crossing was predicted to be 0.5 ns, making triplet ethylenedione a transient, yet spectroscopically long-lived molecule. On the other hand, the mono
anion An ion () is an atom or molecule with a net electrical charge. The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by conven ...
of ethylenedione, OCCO, as well as the dianion , called
acetylenediol Acetylenediol, or ethynediol, is a chemical substance with formula HO−C≡C−OH (an ynol). It is the diol of acetylene. Acetylenediol is unstable in the condensed phase, although its tautomer glyoxal (CHO)2 is well known. Detection Acetylen ...
ate, are both stable. Recent theoretical computations suggest that the ''in situ'' preparation and characterization of ethylenedione may be possible through low-energy free-electron induced single-molecule engineering.


Koch's glyoxylide

In the 1940s,
Detroit Detroit ( , ) is the List of municipalities in Michigan, most populous city in the U.S. state of Michigan. It is situated on the bank of the Detroit River across from Windsor, Ontario. It had a population of 639,111 at the 2020 United State ...
physician William Frederick Koch claimed that he had synthesized this compound, which he called glyoxylide, and that it was an
antidote An antidote is a substance that can counteract a form of poisoning. The term ultimately derives from the Greek term φάρμακον ἀντίδοτον ''(pharmakon antidoton)'', "(medicine) given as a remedy". An older term in English which is ...
to the
toxins A toxin is a naturally occurring poison produced by metabolic activities of living cells or organisms. They occur especially as proteins, often conjugated. The term was first used by organic chemist Ludwig Brieger (1849–1919), derived ...
that caused a long list of ailments, including
diabetes Diabetes mellitus, commonly known as diabetes, is a group of common endocrine diseases characterized by sustained high blood sugar levels. Diabetes is due to either the pancreas not producing enough of the hormone insulin, or the cells of th ...
and
cancer Cancer is a group of diseases involving Cell growth#Disorders, abnormal cell growth with the potential to Invasion (cancer), invade or Metastasis, spread to other parts of the body. These contrast with benign tumors, which do not spread. Po ...
. The claims were false and the drug was classified as a fraud by the
FDA The United States Food and Drug Administration (FDA or US FDA) is a federal agency of the Department of Health and Human Services. The FDA is responsible for protecting and promoting public health through the control and supervision of food ...
.


See also

*
Cyclohexanehexone Cyclohexanehexone, also known as hexaketocyclohexane and triquinoyl, is an organic compound with formula , the sixfold ketone of cyclohexane. It is an oxide of carbon (an oxocarbon), a hexamer of carbon monoxide. The compound is expected to be hi ...
C6O6, also called triquinoyl, formally a trimer of ethylene dione. *
Oxocarbons In chemistry, an oxocarbon or oxide of carbon is a chemical compound consisting only of carbon and oxygen. The simplest and most common oxocarbons are carbon monoxide (CO) and carbon dioxide (). Many other stable (practically if not thermodynamica ...


References

{{Inorganic compounds of carbon Oxocarbons Heterocumulenes Conjugated ketones