Vinyl alcohol

Names

IUPAC name

Ethenol

Other names

Hydroxyethene
Hydroxyethylene

Identifiers

557-75-5^Y

ChEMBL76101^Y

10726^Y

InChI=1S/C2H4O/c1-2-3/h2-3H,1H2^Y
Key: IMROMDMJAWUWLK-UHFFFAOYSA-N^Y
InChI=1S/C2H4O/c1-2-3/h2-3H,1H2
InChI=1S/C2H4O/c1-2-3/h2-3H,1H2
Key: IMROMDMJAWUWLK-UHFFFAOYSA-N

SMILES

OC=C

Properties

Chemical formula

C₂H₄O

Molar mass

44.053 g/mol

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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Infobox references

Vinyl alcohol, also called ethenol (IUPAC name), is an alcohol. It is not to be confused with the drinking alcohol, ethanol. With the formula C H₂CHOH, vinyl alcohol is an isomer of acetaldehyde and ethylene oxide.

Tautomerization of acetaldehyde to vinyl alcohol

Under normal conditions, vinyl alcohol converts (tautomerizes) to acetaldehyde:

At room temperature, acetaldehyde (H₃CC(O)H) is more stable than vinyl alcohol (H₂C=CHOH) by 42.7 kJ/mol:^[1]

H₂C=CHOH → H₃CC(O)H ΔH_298,g = −42.7 kJ/mol

This keto-enol tautomerization has a high barrier and does therefore not occur near room temperature. This tautomerization can be catalyzed via photochemical process. These findings suggest that the keto-enol tautomerization is a viable route under atmospheric and stratospheric conditions, relevant to a role for vinyl alcohol in the production of organic acids in the atmosphere.^[2]^[3]

Relationship to polyvinylalcohol

Because of the instability of vinyl alcohol, the thermoplastic polyvinyl alcohol (PVA or PVOH) is made indirectly by polymerization of vinyl acetate followed by hydrolysis of the ester bonds (Ac = acetyl, HOAc = acetic acid):

n CH₂=CHOAc → (CH₂−CHOAc)_n

(CH₂−CHOAc)_n + n H₂O → (CH₂−CHOH)_n + n HOAc

As a ligand

Several metal complexes are known that contain vinyl alcohol as a ligand. One example is Pt(acac)(η²-C₂H₃OH)Cl.^[4]

Occurrence in interstellar medium

Vinyl alcohol was discovered in the molecular cloud Sagittarius B using the 12-meter radio telescope at the Kitt Peak National Observatory.^[5] This vinyl alcohol being stable in the (dilute) interstellar medium shows that its tautomerization is not unimolecular.

References

↑ R.D. Johnson III. "CCCBDB NIST Standard Reference Database.". Retrieved 2014-08-30.
↑ Heazlewood, B. R.; Maccarone, A. T.; Andrews, D. U.; Osborn, D. L.; Harding, L. B.; Klippenstein, S. J.; Jordan, M. J. T.; Kable, S. H. "Near-threshold H/D exchange in CD₃CHO photodissociation." Nat. Chem. 2011, 3, 443−448. doi:10.1038/nchem.1052
↑ Andrews, D. U.; Heazlewood, B. R.; Maccarone, A. T.; Conroy, T.; Payne, R. J.; Jordan, M. J. T.; Kable, S. H. "Photo-tautomerization of acetaldehyde to vinyl alcohol: A potential route to tropospheric acids." Science 2012, 337, 1203−1206. doi:10.1126/science.1220712
↑ F. A. Cotton, J. N. Francis, B. A. Frenz, M. Tsutsui "Structure of a dihapto(vinyl alcohol) complex of platinum(II)" Journal of the American Chemical Society, 1973, volume 95, p. 2483-6. doi:10.1021/ja00789a011
↑ "Scientists Toast the Discovery of Vinyl Alcohol in Interstellar Space". National Radio Astronomy Observatory. 2001-10-01. Retrieved 2006-12-20.

Molecules detected in outer space

Molecules

Diatomic	Aluminium monochloride Aluminium monofluoride Aluminium monoxide Argon hydride Carbon monophosphide Carbon monosulfide Carbon monoxide Carborundum Cyanogen radical Diatomic carbon Fluoromethylidynium Hydrogen chloride Hydrogen fluoride Hydrogen (molecular) Hydroxyl radical Iron(II) oxide Magnesium monohydride cation Methylidyne radical Nitric oxide Nitrogen (molecular) Nitrogen monohydride Nitrogen sulfide Oxygen (molecular) Phosphorus monoxide Phosphorus mononitride Potassium chloride Silicon carbide Silicon mononitride Silicon monoxide Silicon monosulfide Sodium chloride Sodium iodide Sulfur monohydride Sulfur monoxide Titanium oxide

Triatomic	Aluminium hydroxide Aluminium isocyanide Amino radical Carbon dioxide Carbonyl sulfide CCP radical Chloronium Diazenylium Dicarbon monoxide Disilicon carbide Ethynyl radical Formyl radical Hydrogen cyanide Hydrogen isocyanide (HCN) Hydrogen isocyanide (HNC) Hydrogen sulfide Hydroperoxyl Iron cyanide Isoformyl Magnesium cyanide Magnesium isocyanide Methylene radical N₂H⁺ Nitrous oxide Nitroxyl Ozone Phosphaethyne Potassium cyanide Protonated molecular hydrogen Sodium cyanide Sodium hydroxide Silicon carbonitride c-Silicon dicarbide Silicon naphthalocyanine Sulfur dioxide Thioformyl Thioxoethenylidene Titanium dioxide Tricarbon Water

Four atoms	Acetylene Ammonia Cyanic acid Cyanoethynyl Cyclopropynylidyne Formaldehyde Fulminic acid HCCN Hydrogen peroxide Hydromagnesium isocyanide Isocyanic acid Isothiocyanic acid Ketenyl Methylene amidogen Methyl radical Propynylidyne Protonated carbon dioxide Protonated hydrogen cyanide Silicon tricarbide Thioformaldehyde Tricarbon monoxide Tricarbon sulfide Thiocyanic acid

Five atoms	Ammonium Ion Butadiynyl Carbodiimide Cyanamide Cyanoacetylene Cyanoformaldehyde Cyanomethyl Cyclopropenylidene Formic acid Isocyanoacetylene Ketene Methane Methoxy radical Methylenimine Propadienylidene Protonated formaldehyde Protonated formaldehyde Silane Silicon-carbide cluster

Six atoms	Acetonitrile Cyanobutadiynyl radical E-Cyanomethanimine Cyclopropenone Diacetylene Ethylene Formamide HC₄N Ketenimine Methanethiol Methanol Methyl isocyanide Pentynylidyne Propynal Protonated cyanoacetylene

Seven atoms	Acetaldehyde Acrylonitrile Cyanodiacetylene Ethylene oxide Hexatriynyl radical Methylacetylene Methylamine Methyl isocyanate Vinyl alcohol

Eight atoms	Acetic acid Aminoacetonitrile Cyanoallene Ethanimine Glycolaldehyde Heptatrienyl radical Hexapentaenylidene Methylcyanoacetylene Methyl formate Propenal

Nine atoms	Acetamide Cyanohexatriyne Cyanotriacetylene Dimethyl ether Ethanol Methyldiacetylene Octatetraynyl radical Propene Propionitrile

Ten atoms or more	Acetone Benzene Buckminsterfullerene (C₆₀ fullerene) ("bucky-ball") C₇₀ fullerene Cyanodecapentayne Cyanopentaacetylene Cyanotetra-acetylene Ethylene glycol Ethyl formate Methyl acetate Methyl-cyano-diacetylene Methyltriacetylene Propanal n-Propyl cyanide Pyrimidine

Deuterated
molecules

Unconfirmed

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