Hydroxyl radical
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| Names | |||
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| IUPAC name
Hydroxyl radical
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| Systematic IUPAC name | |||
Other names
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| Identifiers | |||
CAS Number
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3D model (JSmol)
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| ChEBI | |||
| ChemSpider | |||
Gmelin Reference
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105 | ||
| KEGG | |||
PubChem CID
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CompTox Dashboard (EPA)
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InChI
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SMILES
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| Properties | |||
Chemical formula
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HO | ||
| Molar mass | 17.007 g·mol−1 | ||
| Acidity (pKa) | 11.8 to 11.9[2] | ||
| Thermochemistry | |||
Std molar
entropy (S⦵298) |
183.71 J K−1 mol−1 | ||
Std enthalpy of
formation (ΔfH⦵298) |
38.99 kJ mol−1 | ||
| Related compounds | |||
Related compounds
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O2H+ OH− O22− | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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The hydroxyl radical, denoted as •OH or HO•,[a] is the neutral form of the hydroxide ion (OH–). As a free radical, it is highly reactive and consequently short-lived, making it a pivotal species in radical chemistry.[3]
In nature, hydroxyl radicals are most notably produced from the decomposition of hydroperoxides (ROOH) or, in atmospheric chemistry, by the reaction of excited atomic oxygen with water. They are also significant in radiation chemistry, where their formation can lead to hydrogen peroxide and oxygen, which in turn can accelerate corrosion and stress corrosion cracking in environments such as nuclear reactor coolant systems. Other important formation pathways include the UV-light dissociation of hydrogen peroxide (H2O2) and the Fenton reaction, where trace amounts of reduced transition metals catalyze the breakdown of peroxide.
In organic synthesis, hydroxyl radicals are most commonly generated by photolysis of 1-Hydroxy-2(1H)-pyridinethione.
The hydroxyl radical is often referred to as the "detergent" of the troposphere because it reacts with many pollutants, often acting as the first step to their removal. It also has an important role in eliminating some greenhouse gases like methane and ozone.[4] The rate of reaction with the hydroxyl radical often determines how long many pollutants last in the atmosphere, if they do not undergo photolysis or are rained out. For instance, methane, which reacts relatively slowly with hydroxyl radicals, has an average lifetime of >5 years and many CFCs have lifetimes of 50+ years. Pollutants, such as larger hydrocarbons, can have very short average lifetimes of less than a few hours.
The first reaction with many volatile organic compounds (VOCs) is the removal of a hydrogen atom, forming water and an alkyl radical (R•):
- •OH + RH → H2O + R•
The alkyl radical will typically react rapidly with oxygen forming a peroxy radical:
- R• + O2 → RO2•
The fate of this radical in the troposphere is dependent on factors such as the amount of sunlight, pollution in the atmosphere and the nature of the alkyl radical that formed it (see chapters 12 & 13 in External Links "University Lecture notes on Atmospheric chemistry").
- ^ a b "Hydroxyl (CHEBI:29191)". Chemical Entities of Biological Interest (ChEBI). UK: European Bioinformatics Institute.
- ^ Perrin, D. D., ed. (1982) [1969]. Ionisation Constants of Inorganic Acids and Bases in Aqueous Solution. IUPAC Chemical Data (2nd ed.). Oxford: Pergamon (published 1984). Entry 32. ISBN 0-08-029214-3. LCCN 82-16524.
- ^ Finlayson-Pitts, Barbara J.; Pitts, James N. (2000). Chemistry of the Upper and Lower Atmosphere. Academic Press. ISBN 978-0-12-257060-5.
- ^ Forster, P.; V. Ramaswamy; P. Artaxo; T. Berntsen; R. Betts; D.W. Fahey; J. Haywood; J. Lean; D.C. Lowe; G. Myhre; J. Nganga; R. Prinn; G. Raga; M. Schulz; R. Van Dorland (2007). "Changes in Atmospheric Constituents and in Radiative Forcing" (PDF). In Solomon, S.; D. Qin; M. Manning; Z. Chen; M. Marquis; K.B. Averyt; M.Tignor; H.L. Miller (eds.). Climate Change 2007: The Physical Science Basis. Contribution of Working Group I to the Fourth Assessment Report of the Intergovernmental Panel on Climate Change. Cambridge University Press.
The hydroxyl free radical (OH) is the major oxidizing chemical in the atmosphere, destroying about 3.7 Gt of trace gases, including CH4 and all HFCs and HCFCs, each year (Ehhalt, 1999).
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