Hydroxy group

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Representation of an organic compound hydroxy group, where R represents a hydrocarbon or other organic moiety, the red and grey spheres represent oxygen and hydrogen atoms respectively, and the rod-like connections between these, covalent chemical bonds. Hydroxyl3D.png
Representation of an organic compound hydroxy group, where R represents a hydrocarbon or other organic moiety, the red and grey spheres represent oxygen and hydrogen atoms respectively, and the rod-like connections between these, covalent chemical bonds.

In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula −OH and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy groups. Both the negatively charged anion HO−, called hydroxide, and the neutral radical HO·, known as the hydroxyl radical, consist of an unbonded hydroxy group.

Contents

According to IUPAC definitions, the term hydroxyl refers to the hydroxyl radical (·OH) only, while the functional group −OH is called a hydroxy group. [1]

Properties

Sulfuric acid contains two hydroxy groups. Sulfuric-acid-2D-dimensions.svg
Sulfuric acid contains two hydroxy groups.

Water, alcohols, carboxylic acids, and many other hydroxy-containing compounds can be readily deprotonated due to a large difference between the electronegativity of oxygen (3.5) and that of hydrogen (2.1). Hydroxy-containing compounds engage in intermolecular hydrogen bonding increasing the electrostatic attraction between molecules and thus to higher boiling and melting points than found for compounds that lack this functional group. Organic compounds, which are often poorly soluble in water, become water-soluble when they contain two or more hydroxy groups, as illustrated by sugars and amino acid.[ citation needed ]

Occurrence

The hydroxy group is pervasive in chemistry and biochemistry. Many inorganic compounds contain hydroxyl groups, including sulfuric acid, the chemical compound produced on the largest scale industrially. [2]

Hydroxy groups participate in the dehydration reactions that link simple biological molecules into long chains. The joining of a fatty acid to glycerol to form a triacylglycerol removes the −OH from the carboxy end of the fatty acid. The joining of two aldehyde sugars to form a disaccharide removes the −OH from the carboxy group at the aldehyde end of one sugar. The creation of a peptide bond to link two amino acids to make a protein removes the −OH from the carboxy group of one amino acid.[ citation needed ]

Hydroxyl radical

Hydroxyl radicals are highly reactive and undergo chemical reactions that make them short-lived. When biological systems are exposed to hydroxyl radicals, they can cause damage to cells, including those in humans, where they can react with DNA, lipids, and proteins. [3]

Planetary observations

Airglow of the Earth

The Earth's night sky is illuminated by diffuse light, called airglow, that is produced by radiative transitions of atoms and molecules. [4] Among the most intense such features observed in the Earth's night sky is a group of infrared transitions at wavelengths between 700 nanometers and 900 nanometers. In 1950, Aden Meinel showed that these were transitions of the hydroxyl molecule, OH. [5]

Surface of the Moon

In 2009, India's Chandrayaan-1 satellite and the National Aeronautics and Space Administration (NASA) Cassini spacecraft and Deep Impact probe each detected evidence of water by evidence of hydroxyl fragments on the Moon. As reported by Richard Kerr, "A spectrometer [the Moon Mineralogy Mapper, also known as "M3"] detected an infrared absorption at a wavelength of 3.0 micrometers that only water or hydroxyl—a hydrogen and an oxygen bound together—could have created." [6] NASA also reported in 2009 that the LCROSS probe revealed an ultraviolet emission spectrum consistent with hydroxyl presence. [7]

On 26 October 2020, NASA reported definitive evidence of water on the sunlit surface of the Moon, in the vicinity of the crater Clavius (crater), obtained by the Stratospheric Observatory for Infrared Astronomy (SOFIA). [8] The SOFIA Faint Object infrared Camera for the SOFIA Telescope (FORCAST) detected emission bands at a wavelength of 6.1 micrometers that are present in water but not in hydroxyl. The abundance of water on the Moon's surface was inferred to be equivalent to the contents of a 12-ounce bottle of water per cubic meter of lunar soil. [9]

The Chang'e 5 probe, which landed on the Moon on 1 December 2020, carried a mineralogical spectrometer that could measure infrared reflectance spectra of lunar rock and regolith. The reflectance spectrum of a rock sample at a wavelength of 2.85 micrometers indicated localized water/hydroxyl concentrations as high as 180 parts per million. [10]

Atmosphere of Venus

The Venus Express orbiter collected Venus science data from April 2006 until December 2014. In 2008, Piccioni, et al. reported measurements of night-side airglow emission in the atmosphere of Venus made with the Visible and Infrared Thermal Imaging Spectrometer (VIRTIS) on Venus Express. They attributed emission bands in wavelength ranges of 1.40 - 1.49 micrometers and 2.6 - 3.14 micrometers to vibrational transitions of OH. [11] This was the first evidence for OH in the atmosphere of any planet other than Earth's. [11]

Atmosphere of Mars

In 2013, OH near-infrared spectra were observed in the night glow in the polar winter atmosphere of Mars by use of the Compact Reconnaissance Imaging Spectrometer for Mars (CRISM). [12]

Exoplanets

In 2021, evidence for OH in the dayside atmosphere of the exoplanet WASP-33b was found in its emission spectrum at wavelengths between 1 and 2 micrometers. [13] Evidence for OH in the atmosphere of exoplanet WASP-76b was subsequently found. [14] Both WASP-33b and WASP-76b are ultra-hot Jupiters and it is likely that any water in their atmospheres is present as dissociated ions.

See also

Related Research Articles

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In chemistry, an alcohol is a type of organic compound that carries at least one hydroxyl functional group bound to a saturated carbon atom. Alcohols range from the simple, like methanol and ethanol, to complex, like sugar alcohols and cholesterol. The presence of an OH group strongly modifies the properties of hydrocarbons, conferring hydrophilic (water-loving) properties. The OH group provides a site at which many reactions can occur.

Infrared astronomy is a sub-discipline of astronomy which specializes in the observation and analysis of astronomical objects using infrared (IR) radiation. The wavelength of infrared light ranges from 0.75 to 300 micrometers, and falls in between visible radiation, which ranges from 380 to 750 nanometers, and submillimeter waves.

<span class="mw-page-title-main">Astrochemistry</span> Study of molecules in the Universe and their reactions

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<span class="mw-page-title-main">Pioneer Venus project</span> Two spacecraft send to Venus in 1978

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<span class="mw-page-title-main">W. M. Keck Observatory</span> Astronomical observatory in Hawaii

The W. M. Keck Observatory is an astronomical observatory with two telescopes at an elevation of 4,145 meters (13,600 ft) near the summit of Mauna Kea in the U.S. state of Hawaii. Both telescopes have 10 m (33 ft) aperture primary mirrors, and, when completed in 1993 and 1996, they were the largest optical reflecting telescopes in the world. They are currently the third and fourth largest.

<span class="mw-page-title-main">Upper Atmosphere Research Satellite</span> NASA-operated orbital observatory (1991-2011)

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<span class="mw-page-title-main">Hydroxyl radical</span> Neutral form of the hydroxide ion (OH−)

The hydroxyl radical, •HO, is the neutral form of the hydroxide ion (HO–). Hydroxyl radicals are highly reactive and consequently short-lived; however, they form an important part of radical chemistry. Most notably hydroxyl radicals are produced from the decomposition of hydroperoxides (ROOH) or, in atmospheric chemistry, by the reaction of excited atomic oxygen with water. It is also an important radical formed in radiation chemistry, since it leads to the formation of hydrogen peroxide and oxygen, which can enhance corrosion and SCC in coolant systems subjected to radioactive environments. Hydroxyl radicals are also produced during UV-light dissociation of H2O2 (suggested in 1879) and likely in Fenton chemistry, where trace amounts of reduced transition metals catalyze peroxide-mediated oxidations of organic compounds.

<span class="mw-page-title-main">Cabeus (crater)</span> Lunar impact crater

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<span class="mw-page-title-main">Airglow</span> Faint emission of light by a planetary atmosphere


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<span class="mw-page-title-main">Life on Venus</span> Scientific assessments on the microbial habitability of Venus

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References

  1. ↑ "Alcohols". Gold Book. IUPAC. February 24, 2014. doi: 10.1351/goldbook.A00204 . Retrieved 23 March 2015.
  2. ↑ "Research Report 2012 – 2013" (PDF). Ludwig Maximilians Universität München Fakultät für Chemie und Pharmazie. 12. Archived from the original (PDF) on Dec 7, 2022.
  3. ↑ Kanno, Taro; Nakamura, Keisuke; Ikai, Hiroyo; Kikuchi, Katsushi; Sasaki, Keiichi; Niwano, Yoshimi (July 2012). "Literature review of the role of hydroxyl radicals in chemically-induced mutagenicity and carcinogenicity for the risk assessment of a disinfection system utilizing photolysis of hydrogen peroxide". Journal of Clinical Biochemistry and Nutrition. 51 (1): 9–14. doi: 10.3164/jcbn.11-105 . ISSN   0912-0009. PMC   3391867 . PMID   22798706.
  4. ↑ Silverman SM (October 1970). "Night airglow phenomenology". Space Science Reviews. 11 (2): 341–79. Bibcode: 1970SSRv...11..341S . doi:10.1007/BF00241526. S2CID   120677542. Archived from the original on Oct 5, 2023.
  5. ↑ Meinel AB (1950). "OH Emission Bands in the Spectrum of the Night Sky. I". Astrophysical Journal. 111: 555–564. Bibcode: 1950ApJ...111..555M . doi: 10.1086/145296 . Archived from the original on Oct 24, 2022.
  6. ↑ Kerr RA (24 September 2009). "A Whiff of Water Found on the Moon". Science. Archived from the original on Dec 8, 2023. Retrieved 2016-06-01.
  7. ↑ Dino J (13 November 2009). "LCROSS Impact Data Indicates Water on Moon". NASA. Archived from the original on 2009-11-15. Retrieved 2009-11-14.
  8. ↑ Honniball CI, Lucey PG, Li S, Shenoy S, Orlando TM, Hibbitts CA, Hurley DM, Farrell WM (2020). "Molecular water detected on the sunlit Moon by SOFIA". Nature Astronomy. 5 (2): 121–127. Bibcode:2021NatAs...5..121H. doi:10.1038/s41550-020-01222-x. S2CID   228954129.
  9. ↑ Chou F, Hawkes A (26 October 2020). "NASA's SOFIA Discovers Water on Sunlit Surface of Moon". NASA . Retrieved 2020-10-26.
  10. ↑ Lin H, Li S, Xu R, Liu Y, Wu X, Yang W, Wei Y, Lin Y, He Z, Hui H, He K, Hu S, Zhang C, Li C, Lv G, Yuan L, Zou Y, Wang C (2022). "In situ detection of water on the Moon by the Chang'E-5 lander". Science Advances. 8 (1): eabl9174. Bibcode:2022SciA....8.9174L. doi:10.1126/sciadv.abl9174. PMC   8741181 . PMID   34995111.
  11. 1 2 Piccioni, G.; Drossart, P.; Zasova, L.; Migliorini, A.; Gérard, J.-C.; Mills, F. P.; Shakun, A.; García Muñoz, A.; Ignatiev, N.; Grassi, D.; Cottini, V.; Taylor, F. W.; Erard, S. (2008-04-01). "First detection of hydroxyl in the atmosphere of Venus". Astronomy & Astrophysics. 483 (3). EDP Sciences: L29–L33. doi: 10.1051/0004-6361:200809761 . hdl: 1885/35639 . ISSN   0004-6361.
  12. ↑ Clancy RT, Sandor BJ, García-Muñoz A, Lefèvre F, Smith MD, Wolff MJ, Montmessin F, Murchie SL, Nair H (2013). "First detection of Mars atmospheric hydroxyl: CRISM Near-IR measurement versus LMD GCM simulation of OH Meinel band emission in the Mars polar winter atmosphere". Icarus. 226 (1): 272–281. Bibcode:2013Icar..226..272T. doi:10.1016/j.icarus.2013.05.035.
  13. ↑ Stevanus K. Nugroho; Hajime Kawahara; Neale P. Gibson; Ernst J. W. de Mooij; Teruyuki Hirano; Takayuki Kotani; Yui Kawashima; Kento Masuda; Matteo Brogi; Jayne L. Birkby; Chris A. Watson; Motohide Tamura; Konstanze Zwintz; Hiroki Harakawa; Tomoyuki Kudo; Masayuki Kuzuhara; Klaus Hodapp; Masato Ishizuka; Shane Jacobson; Mihoko Konishi; Takashi Kurokawa; Jun Nishikawa; Masashi Omiya; Takuma Serizawa; Akitoshi Ueda; Sébastien Vievard (2021). "First Detection of Hydroxyl Radical Emission from an Exoplanet Atmosphere: High-dispersion Characterization of {WASP}-33b Using Subaru/{IRD}" (PDF). Astrophysical Journal Letters. 910 (1): L9. doi: 10.3847/2041-8213/abec71 . S2CID   232110452.
  14. ↑ R. Landman; A. Sánchez-López; P. Mollière; A. Y. Kesseli; A. J. Louca; I. A. G. Snellen (2021). "Detection of OH in the ultra-hot Jupiter WASP-76b". Astronomy and Astrophysics. 656 (1): A119. arXiv: 2110.11946 . Bibcode:2021A&A...656A.119L. doi: 10.1051/0004-6361/202141696 . S2CID   239616465.

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