Nitric oxide: Difference between revisions
Changed the hatlinks as it said not to be confused with nitrogen oxide and article said that nitrogen oxide was an alternative name. Tried to make it clearer but not sure I've got it quite right |
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{{short description|Colorless gas with the formula NO}} |
{{short description|Colorless gas with the formula NO}} |
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{{distinguish|nitrous oxide}} |
{{distinguish|nitrous oxide}} |
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{{About| |
{{About|a molecule of one nitrogen atom and one oxygen atom|other chemical combinations of nitrogen and oxygen|nitrogen oxide|the use of nitric oxide as a medication or in biology|Biological functions of nitric oxide}} |
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{{About|a molecule of one nitrogen atom and one oxygen atom|other chemical combinations of nitrogen and oxygen|nitrogen oxide}} |
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{{Chembox |
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| IUPACName = Nitrogen monoxide<ref name="Nomenclature_2005" /> |
| IUPACName = Nitrogen monoxide<ref name="Nomenclature_2005" /> |
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| SystematicName = Oxidonitrogen(•)<ref>{{cite web|title = Nitric Oxide (CHEBI:16480)|url = https://www.ebi.ac.uk/chebi/searchId.do?chebiId=16480|work = Chemical Entities of Biological Interest (ChEBI)|location = UK|publisher = European Bioinformatics Institute}}</ref> (additive) |
| SystematicName = Oxidonitrogen(•)<ref>{{cite web|title = Nitric Oxide (CHEBI:16480)|url = https://www.ebi.ac.uk/chebi/searchId.do?chebiId=16480|work = Chemical Entities of Biological Interest (ChEBI)|location = UK|publisher = European Bioinformatics Institute}}</ref> (additive) |
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| OtherNames = Nitrogen oxide<br/>Nitrogen(II) oxide<br>Oxonitrogen |
| OtherNames = Nitrogen oxide<br/>Nitrogen(II) oxide<br>Oxonitrogen<br>Nitrogen monoxide |
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| Section1 = {{Chembox Identifiers |
| Section1 = {{Chembox Identifiers |
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| IUPHAR_ligand = 2509 |
| IUPHAR_ligand = 2509 |
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'''Nitric oxide''' (nitrogen oxide or nitrogen monoxide<ref name="Nomenclature_2005">{{cite book |title=Nomenclature of Inorganic Chemistry, IUPAC Recommendations <!-- |title-link=IUPAC nomenclature of inorganic chemistry 2005 --> |url=http://old.iupac.org/publications/books/rbook/Red_Book_2005.pdf |publisher=International Union of Pure and Applied Chemistry |year=2005 |page=69}}</ref>) is a colorless gas with the formula {{chem|NO}}. It is one of the principal [[oxides of nitrogen]]. Nitric oxide is a [[free radical]]: it has an [[unpaired electron]], which is sometimes denoted by a dot in its [[chemical formula]] (<sup>•</sup>N=O or <sup>•</sup>NO). Nitric oxide is also a [[heteronuclear]] [[diatomic molecule]], a class of molecules whose study spawned early modern [[molecular orbital theory|theories of chemical bonding]].<ref name=G&E/> |
'''Nitric oxide''' ('''nitrogen oxide''' or '''nitrogen monoxide'''<ref name="Nomenclature_2005">{{cite book |title=Nomenclature of Inorganic Chemistry, IUPAC Recommendations <!-- |title-link=IUPAC nomenclature of inorganic chemistry 2005 --> |url=http://old.iupac.org/publications/books/rbook/Red_Book_2005.pdf |publisher=International Union of Pure and Applied Chemistry |year=2005 |page=69}}</ref>) is a colorless gas with the formula '''{{chem|NO}}'''. It is one of the principal [[oxides of nitrogen]]. Nitric oxide is a [[free radical]]: it has an [[unpaired electron]], which is sometimes denoted by a dot in its [[chemical formula]] (<sup>•</sup>N=O or <sup>•</sup>NO). Nitric oxide is also a [[heteronuclear]] [[diatomic molecule]], a class of molecules whose study spawned early modern [[molecular orbital theory|theories of chemical bonding]].<ref name="G&E" /> |
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An important [[Reaction intermediate|intermediate]] in [[chemical industry|industrial chemistry]], nitric oxide forms in combustion systems and can be generated by lightning in thunderstorms. In mammals, including humans, nitric oxide is a [[signaling molecule]] in many physiological and pathological processes.<ref>{{cite journal |pmid=10390607 |year=1999 |last1=Hou |first1=Y. C. |last2=Janczuk |first2=A. |last3=Wang |first3=P. G. |title=Current trends in the development of nitric oxide donors |volume=5 |issue=6 |pages=417–441 |journal=Current Pharmaceutical Design}}</ref> It was proclaimed the "[[Molecule of the Year]]" in 1992.<ref name="pmid1361684">{{cite journal |author1=Culotta, Elizabeth |author2=Koshland, Daniel E. Jr. | year = 1992 | title = NO news is good news | journal = Science | volume = 258 | issue = 5090 | pages = 1862–1864 | doi = 10.1126/science.1361684 | pmid = 1361684 |bibcode=1992Sci...258.1862C }}</ref> The [[List of Nobel laureates in Physiology or Medicine#1951.E2.80.932000|1998 Nobel Prize in Physiology or Medicine]] was awarded for discovering nitric oxide's role as a cardiovascular signalling molecule.<ref>{{Cite web |title=The Nobel Prize in Physiology or Medicine 1998 |url=https://www.nobelprize.org/prizes/medicine/1998/summary/ |access-date=2022-06-17 |website=NobelPrize.org |language=en-US}}</ref> |
An important [[Reaction intermediate|intermediate]] in [[chemical industry|industrial chemistry]], nitric oxide forms in combustion systems and can be generated by lightning in thunderstorms. In mammals, including humans, nitric oxide is a [[signaling molecule]] in many physiological and pathological processes.<ref>{{cite journal |pmid=10390607 |year=1999 |last1=Hou |first1=Y. C. |last2=Janczuk |first2=A. |last3=Wang |first3=P. G. |title=Current trends in the development of nitric oxide donors |volume=5 |issue=6 |pages=417–441 |journal=Current Pharmaceutical Design|doi=10.2174/138161280506230110111042 }}</ref> It was proclaimed the "[[Molecule of the Year]]" in 1992.<ref name="pmid1361684">{{cite journal |author1=Culotta, Elizabeth |author2=Koshland, Daniel E. Jr. | year = 1992 | title = NO news is good news | journal = Science | volume = 258 | issue = 5090 | pages = 1862–1864 | doi = 10.1126/science.1361684 | pmid = 1361684 |bibcode=1992Sci...258.1862C }}</ref> The [[List of Nobel laureates in Physiology or Medicine#1951.E2.80.932000|1998 Nobel Prize in Physiology or Medicine]] was awarded for discovering nitric oxide's role as a cardiovascular signalling molecule.<ref>{{Cite web |title=The Nobel Prize in Physiology or Medicine 1998 |url=https://www.nobelprize.org/prizes/medicine/1998/summary/ |access-date=2022-06-17 |website=NobelPrize.org |language=en-US}}</ref> |
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Nitric oxide should not be confused with [[nitrogen dioxide]] (NO<sub>2</sub>), a brown gas and major [[air pollutant]], |
Nitric oxide should not be confused with [[nitrogen dioxide]] (NO<sub>2</sub>), a brown gas and major [[air pollutant]], or with [[nitrous oxide]] (N<sub>2</sub>O), an [[general anaesthetic|anesthetic]] gas.<ref name="G&E"/> |
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==Physical properties== |
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===Electronic configuration=== |
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The ground state electronic configuration of NO is, in united atom notation:<ref>{{cite book |last1=Berkowitz |first1=Joseph |title=Photoabsorption, Photoionization, and Photoelectron Spectroscopy |date=1979 |publisher=Academic Press |page=231 |doi=10.1016/B978-0-12-091650-4.50012-8 |url=https://doi.org/10.1016/B978-0-12-091650-4.50012-8}}</ref> |
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<math display="block">(1\sigma)^2(2\sigma)^2(3\sigma)^2(4\sigma^*)^2(5\sigma)^2(1\pi)^4(2\pi^*)^1</math> |
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The first two orbitals are actually pure atomic 1''s''<sub>O</sub> and 1''s''<sub>N</sub> from oxygen and nitrogen respectively and therefore are usually not noted in the united atom notation. Orbitals noted with an asterisk are antibonding. The ordering of 5σ and 1π according to their binding energies is subject to discussion. Removal of a 1π electron leads to 6 states whose energies span over a range starting at a lower level than a 5σ electron an extending to a higher level. This is due to the different orbital momentum couplings between a 1π and a 2π electron. |
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The lone electron in the 2π orbital makes NO a doublet (X ²Π) in its ground state whose degeneracy is split in the fine structure from spin-orbit coupling with a total momentum ''J''={{frac|3|2}} or ''J''={{frac|1|2}}. |
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===Dipole=== |
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The dipole of NO has been measured experimentally to 0.15740 D and is oriented from O to N (⁻NO⁺) due to the transfer of negative electronic charge from oxygen to nitrogen. <ref>{{cite journal |first1=A. R. |last1=Hoy |first2=J. W. C. |last2=Johns |first3=A. R. W. |last3=McKellar |title=Stark Spectroscopy with the CO Laser: Dipole Moments, Hyperfine Structure, and Level Crossing Effects in the Fundamental Band of NO |journal=Canadian Journal of Physics |date=1975 |volume=53 |issue=19 |pages=2029–2039|doi=10.1139/p75-254 |bibcode=1975CaJPh..53.2029H |url=https://doi.org/10.1139/p75-254}}</ref> |
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==Reactions== |
==Reactions== |
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Since the heat of formation of <sup>•</sup>NO is [[endothermic]], NO can be decomposed to the elements. [[Catalytic converter]]s in cars exploit this reaction: |
Since the heat of formation of <sup>•</sup>NO is [[endothermic]], NO can be decomposed to the elements. [[Catalytic converter]]s in cars exploit this reaction: |
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: 2 NO → O<sub>2</sub> + N<sub>2</sub> |
: 2 <sup>•</sup>NO → O<sub>2</sub> + N<sub>2</sub> |
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When exposed to [[oxygen]], nitric oxide converts into [[nitrogen dioxide]]: |
When exposed to [[oxygen]], nitric oxide converts into [[nitrogen dioxide]]: |
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: 2 NO + O<sub>2</sub> → 2 NO<sub>2</sub> |
: 2 <sup>•</sup>NO + O<sub>2</sub> → 2 <sup>•</sup>NO<sub>2</sub> |
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This reaction is thought to occur via the intermediates ONOO<sup>•</sup> and the red compound ONOONO.<ref name="Galliker Kissner Nauser Koppenol pp. 6161–6168">{{cite journal | last1=Galliker | first1=Benedikt | last2=Kissner | first2=Reinhard | last3=Nauser | first3=Thomas | last4=Koppenol | first4=Willem H. | display-authors=1 | title=Intermediates in the Autoxidation of Nitrogen Monoxide | journal=Chemistry - A European Journal | volume=15 | issue=25 | date=2009 | issn=0947-6539 | doi=10.1002/chem.200801819 | pages=6161–6168| pmid=19437472 }}</ref> |
This reaction is thought to occur via the intermediates ONOO<sup>•</sup> and the red compound ONOONO.<ref name="Galliker Kissner Nauser Koppenol pp. 6161–6168">{{cite journal | last1=Galliker | first1=Benedikt | last2=Kissner | first2=Reinhard | last3=Nauser | first3=Thomas | last4=Koppenol | first4=Willem H. | display-authors=1 | title=Intermediates in the Autoxidation of Nitrogen Monoxide | journal=Chemistry - A European Journal | volume=15 | issue=25 | date=2009 | issn=0947-6539 | doi=10.1002/chem.200801819 | pages=6161–6168| pmid=19437472 }}</ref> |
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In water, nitric oxide reacts with oxygen to form [[nitrous acid]] (HNO<sub>2</sub>). The reaction is thought to proceed via the following [[stoichiometry]]: |
In water, nitric oxide reacts with oxygen to form [[nitrous acid]] (HNO<sub>2</sub>). The reaction is thought to proceed via the following [[stoichiometry]]: |
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: 4 NO + O<sub>2</sub> + 2 H<sub>2</sub>O → 4 HNO<sub>2</sub> |
: 4 <sup>•</sup>NO + O<sub>2</sub> + 2 H<sub>2</sub>O → 4 HNO<sub>2</sub> |
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Nitric oxide reacts with [[fluorine]], [[chlorine]], and [[bromine]] to form the nitrosyl halides, such as [[nitrosyl chloride]]: |
Nitric oxide reacts with [[fluorine]], [[chlorine]], and [[bromine]] to form the nitrosyl halides, such as [[nitrosyl chloride]]: |
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: 2 NO + Cl<sub>2</sub> → 2 NOCl |
: 2 <sup>•</sup>NO + Cl<sub>2</sub> → 2 NOCl |
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With NO<sub>2</sub>, also a radical, NO combines to form the intensely blue [[dinitrogen trioxide]]:<ref name=G&E/> |
With NO<sub>2</sub>, also a radical, NO combines to form the intensely blue [[dinitrogen trioxide]]:<ref name=G&E/> |
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: NO + NO<sub>2</sub> {{eqm}} ON−NO<sub>2</sub> |
: <sup>•</sup>NO + <sup>•</sup>NO<sub>2</sub> {{eqm}} ON−NO<sub>2</sub> |
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===Organic chemistry=== |
===Organic chemistry=== |
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The addition of a nitric oxide [[Moiety (chemistry)|moiety]] to another molecule is often referred to as ''[[nitrosylation]]''. The '''Traube reaction'''<ref>{{confused|Traube purine synthesis}}</ref> is the [[addition reaction|addition]] of a two [[equivalent (chemistry)|equivalent]]s of nitric oxide onto an [[enolate]], giving a diazeniumdiolate (also called a ''nitrosohydroxylamine'').<ref>{{cite journal |title= Synthesis of Diazeniumdiolates from the Reactions of Nitric Oxide with Enolates |first1= Navamoney |last1= Arulsamy |first2= D. Scott |last2= Bohle |journal= J. Org. Chem. |year= 2006 |volume= 71 |issue= 2 |pages= 572–581 |doi= 10.1021/jo051998p |pmid= 16408967 }}</ref> The product can undergo a subsequent retro-[[aldol reaction]], giving an overall process similar to the [[haloform reaction]]. For example, nitric oxide reacts with [[acetone]] and an [[alkoxide]] to form a diazeniumdiolate on each [[alpha carbon|α position]], with subsequent loss of [[methyl acetate]] as a [[by-product]]:<ref>{{cite journal |doi=10.1002/jlac.18983000108 |title=Ueber Synthesen stickstoffhaltiger Verbindungen mit Hülfe des Stickoxyds |year=1898 |last1=Traube |first1=Wilhelm |journal=Justus Liebig's Annalen der Chemie |volume=300 |pages=81–128 |language=de|url=https://zenodo.org/record/1427495 }}</ref> |
The addition of a nitric oxide [[Moiety (chemistry)|moiety]] to another molecule is often referred to as ''[[nitrosylation]]''. The '''Traube reaction'''<ref>{{confused|Traube purine synthesis}}</ref> is the [[addition reaction|addition]] of a two [[equivalent (chemistry)|equivalent]]s of nitric oxide onto an [[enolate]], giving a diazeniumdiolate (also called a ''nitrosohydroxylamine'').<ref>{{cite journal |title= Synthesis of Diazeniumdiolates from the Reactions of Nitric Oxide with Enolates |first1= Navamoney |last1= Arulsamy |first2= D. Scott |last2= Bohle |journal= J. Org. Chem. |year= 2006 |volume= 71 |issue= 2 |pages= 572–581 |doi= 10.1021/jo051998p |pmid= 16408967 }}</ref> The product can undergo a subsequent retro-[[aldol reaction]], giving an overall process similar to the [[haloform reaction]]. For example, nitric oxide reacts with [[acetone]] and an [[alkoxide]] to form a diazeniumdiolate on each [[alpha carbon|α position]], with subsequent loss of [[methyl acetate]] as a [[by-product]]:<ref>{{cite journal |doi=10.1002/jlac.18983000108 |title=Ueber Synthesen stickstoffhaltiger Verbindungen mit Hülfe des Stickoxyds |year=1898 |last1=Traube |first1=Wilhelm |journal=Justus Liebig's Annalen der Chemie |volume=300 |issue=1 |pages=81–128 |language=de|url=https://zenodo.org/record/1427495 }}</ref> |
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: [[File:TraubeReaction.svg|400px|Traube reaction]] |
: [[File:TraubeReaction.svg|400px|Traube reaction]] |
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In commercial settings, nitric oxide is produced by the [[oxidation]] of [[ammonia]] at 750–900 °C (normally at 850 °C) with [[platinum]] as [[catalyst]] in the [[Ostwald process]]: |
In commercial settings, nitric oxide is produced by the [[oxidation]] of [[ammonia]] at 750–900 °C (normally at 850 °C) with [[platinum]] as [[catalyst]] in the [[Ostwald process]]: |
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:4 NH<sub>3</sub> + 5 O<sub>2</sub> → 4 NO + 6 H<sub>2</sub>O |
:4 NH<sub>3</sub> + 5 O<sub>2</sub> → 4 <sup>•</sup>NO + 6 H<sub>2</sub>O |
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The uncatalyzed [[endothermic]] reaction of [[oxygen]] (O<sub>2</sub>) and [[nitrogen]] (N<sub>2</sub>), which is effected at high temperature (>2000 °C) by lightning has not been developed into a practical commercial synthesis (see [[Birkeland–Eyde process]]): |
The uncatalyzed [[endothermic]] reaction of [[oxygen]] (O<sub>2</sub>) and [[nitrogen]] (N<sub>2</sub>), which is effected at high temperature (>2000 °C) by lightning has not been developed into a practical commercial synthesis (see [[Birkeland–Eyde process]]): |
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:N<sub>2</sub> + O<sub>2</sub> → 2 NO |
:N<sub>2</sub> + O<sub>2</sub> → 2 <sup>•</sup>NO |
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===Laboratory methods=== |
===Laboratory methods=== |
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In the laboratory, nitric oxide is conveniently generated by reduction of dilute [[nitric acid]] with [[copper]]: |
In the laboratory, nitric oxide is conveniently generated by reduction of dilute [[nitric acid]] with [[copper]]: |
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:8 HNO<sub>3</sub> + 3 Cu → 3 Cu(NO<sub>3</sub>)<sub>2</sub> + 4 H<sub>2</sub>O + 2 NO |
:8 HNO<sub>3</sub> + 3 Cu → 3 Cu(NO<sub>3</sub>)<sub>2</sub> + 4 H<sub>2</sub>O + 2 <sup>•</sup>NO |
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An alternative route involves the reduction of nitrous acid in the form of [[sodium nitrite]] or [[potassium nitrite]]: |
An alternative route involves the reduction of nitrous acid in the form of [[sodium nitrite]] or [[potassium nitrite]]: |
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: 2 NaNO<sub>2</sub> + 2 NaI + 2 H<sub>2</sub>SO<sub>4</sub> → I<sub>2</sub> + 2 Na<sub>2</sub>SO<sub>4</sub> + 2 H<sub>2</sub>O + 2 NO |
: 2 NaNO<sub>2</sub> + 2 NaI + 2 H<sub>2</sub>SO<sub>4</sub> → I<sub>2</sub> + 2 Na<sub>2</sub>SO<sub>4</sub> + 2 H<sub>2</sub>O + 2 <sup>•</sup>NO |
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: 2 NaNO<sub>2</sub> + 2 FeSO<sub>4</sub> + 3 H<sub>2</sub>SO<sub>4</sub> → Fe<sub>2</sub>(SO<sub>4</sub>)<sub>3</sub> + 2 NaHSO<sub>4</sub> + 2 H<sub>2</sub>O + 2 NO |
: 2 NaNO<sub>2</sub> + 2 FeSO<sub>4</sub> + 3 H<sub>2</sub>SO<sub>4</sub> → Fe<sub>2</sub>(SO<sub>4</sub>)<sub>3</sub> + 2 NaHSO<sub>4</sub> + 2 H<sub>2</sub>O + 2 <sup>•</sup>NO |
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: 3 KNO<sub>2</sub> + KNO<sub>3</sub> + Cr<sub>2</sub>O<sub>3</sub> → 2 K<sub>2</sub>CrO<sub>4</sub> + 4 NO |
: 3 KNO<sub>2</sub> + KNO<sub>3</sub> + Cr<sub>2</sub>O<sub>3</sub> → 2 K<sub>2</sub>CrO<sub>4</sub> + 4 <sup>•</sup>NO |
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The iron(II) sulfate route is simple and has been used in undergraduate laboratory experiments. So-called [[NONOate]] compounds are also used for nitric oxide generation. |
The iron(II) sulfate route is simple and has been used in undergraduate laboratory experiments. So-called [[NONOate]] compounds are also used for nitric oxide generation. |
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Nitric oxide concentration can be determined using a [[chemiluminescence|chemiluminescent reaction]] involving [[ozone]].<ref>{{cite journal |title=Homogeneous chemiluminescent measurement of nitric oxide with ozone. Implications for continuous selective monitoring of gaseous air pollutants|year=1970 |last1=Fontijn |first1=Arthur |last2=Sabadell |first2=Alberto J. |last3=Ronco |first3=Richard J. |journal=Analytical Chemistry |volume=42 |issue=6 |pages=575–579 |doi=10.1021/ac60288a034}}</ref> A sample containing nitric oxide is mixed with a large quantity of ozone. The nitric oxide reacts with the ozone to produce [[oxygen]] and [[nitrogen dioxide]], accompanied with emission of [[light]] ([[chemiluminescence]]): |
Nitric oxide concentration can be determined using a [[chemiluminescence|chemiluminescent reaction]] involving [[ozone]].<ref>{{cite journal |title=Homogeneous chemiluminescent measurement of nitric oxide with ozone. Implications for continuous selective monitoring of gaseous air pollutants|year=1970 |last1=Fontijn |first1=Arthur |last2=Sabadell |first2=Alberto J. |last3=Ronco |first3=Richard J. |journal=Analytical Chemistry |volume=42 |issue=6 |pages=575–579 |doi=10.1021/ac60288a034}}</ref> A sample containing nitric oxide is mixed with a large quantity of ozone. The nitric oxide reacts with the ozone to produce [[oxygen]] and [[nitrogen dioxide]], accompanied with emission of [[light]] ([[chemiluminescence]]): |
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: NO + O<sub>3</sub> → NO<sub>2</sub> + O<sub>2</sub> + ''hν'' |
: <sup>•</sup>NO + O<sub>3</sub> → <sup>•</sup>NO<sub>2</sub> + O<sub>2</sub> + ''hν'' |
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which can be measured with a [[photodetector]]. The amount of light produced is proportional to the amount of nitric oxide in the sample. |
which can be measured with a [[photodetector]]. The amount of light produced is proportional to the amount of nitric oxide in the sample. |
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Other methods of testing include [[electrochemistry|electroanalysis]] (amperometric approach), where ·NO reacts with an electrode to induce a current or voltage change. The detection of NO radicals in biological tissues is particularly difficult due to the short lifetime and concentration of these radicals in tissues. One of the few practical methods is [[spin trapping]] of nitric oxide with iron-[[dithiocarbamate]] complexes and subsequent detection of the mono-nitrosyl-iron complex with [[electron paramagnetic resonance]] (EPR).<ref>{{cite book |last1=Vanin |first1=A |last2=Huisman |first2=A |last3=Van Faassen |first3=E | |
Other methods of testing include [[electrochemistry|electroanalysis]] (amperometric approach), where ·NO reacts with an electrode to induce a current or voltage change. The detection of NO radicals in biological tissues is particularly difficult due to the short lifetime and concentration of these radicals in tissues. One of the few practical methods is [[spin trapping]] of nitric oxide with iron-[[dithiocarbamate]] complexes and subsequent detection of the mono-nitrosyl-iron complex with [[electron paramagnetic resonance]] (EPR).<ref>{{cite book |last1=Vanin |first1=A |last2=Huisman |first2=A |last3=Van Faassen |first3=E |title=Nitric Oxide, Part D: Oxide Detection, Mitochondria and Cell Functions, and Peroxynitrite Reactions |chapter=Iron dithiocarbamate as spin trap for nitric oxide detection: Pitfalls and successes |year=2002 |volume=359 |pages=[https://archive.org/details/nitricoxide0000unse/page/27 27–42] |pmid=12481557 |doi=10.1016/S0076-6879(02)59169-2 |series=Methods in Enzymology |isbn=9780121822620 |chapter-url=https://archive.org/details/nitricoxide0000unse/page/27 }}</ref><ref>{{cite journal |last1=Nagano |first1=T |last2=Yoshimura |first2=T |year=2002 |title=Bioimaging of nitric oxide |journal=Chemical Reviews |volume=102 |issue=4 |pages=1235–1270 |doi=10.1021/cr010152s |pmid=11942795}}</ref> |
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A group of [[fluorescent dye]] indicators that are also available in [[acetyl]]ated form for intracellular measurements exist. The most common compound is [[4,5-diaminofluorescein]] (DAF-2).<ref name="undefined">{{cite journal |
A group of [[fluorescent dye]] indicators that are also available in [[acetyl]]ated form for intracellular measurements exist. The most common compound is [[4,5-diaminofluorescein]] (DAF-2).<ref name="undefined">{{cite journal |
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=== Acid rain deposition === |
=== Acid rain deposition === |
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Nitric oxide reacts with the [[hydroperoxyl|hydroperoxyl radical]] ({{chem|HO|2|•}}) to form nitrogen dioxide (NO<sub>2</sub>), which then can react with a hydroxyl radical (<sup> |
Nitric oxide reacts with the [[hydroperoxyl|hydroperoxyl radical]] ({{chem|HO|2|•}}) to form nitrogen dioxide (NO<sub>2</sub>), which then can react with a [[hydroxyl radical]] (HO<sup>•</sup>) to produce [[nitric acid]] (HNO<sub>3</sub>): |
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: <sup>•</sup>NO + {{chem|HO|2|•}} → <sup>•</sup>NO<sub>2</sub> + <sup>•</sup> |
: <sup>•</sup>NO + {{chem|HO|2|•}} → <sup>•</sup>NO<sub>2</sub> + HO<sup>•</sup> |
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: <sup>•</sup>NO<sub>2</sub> + <sup>•</sup> |
: <sup>•</sup>NO<sub>2</sub> + HO<sup>•</sup> → HNO<sub>3</sub> |
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Nitric acid, along with [[sulfuric acid]], contributes to [[acid rain]] deposition. |
Nitric acid, along with [[sulfuric acid]], contributes to [[acid rain]] deposition. |
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=== Ozone depletion === |
=== Ozone depletion === |
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<sup>•</sup>NO participates in [[ozone layer depletion]]. Nitric oxide reacts with stratospheric [[ozone]] to form O<sub>2</sub> and nitrogen dioxide: |
<sup>•</sup>NO participates in [[ozone layer depletion]]. Nitric oxide reacts with stratospheric [[ozone]] to form O<sub>2</sub> and nitrogen dioxide: |
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: <sup>•</sup>NO + O<sub>3</sub> → NO<sub>2</sub> + O<sub>2</sub> |
: <sup>•</sup>NO + O<sub>3</sub> → <sup>•</sup>NO<sub>2</sub> + O<sub>2</sub> |
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This reaction is also utilized to measure concentrations of <sup>•</sup>NO in control volumes. |
This reaction is also utilized to measure concentrations of <sup>•</sup>NO in control volumes. |
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==Biological functions== |
==Biological functions== |
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{{Main|Biological functions of nitric oxide}} |
{{Main|Biological functions of nitric oxide}} |
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NO is a [[gaseous signaling molecule]].<ref>{{Cite journal|last1=Liu|first1=Hongying|last2=Weng|first2=Lingyan|last3=Yang|first3=Chi|date=2017-03-28|title=A review on nanomaterial-based electrochemical sensors for H<sub>2</sub>O<sub>2</sub>, H<sub>2</sub>S and NO inside cells or released by cells|journal=Microchimica Acta|volume=184|issue=5|pages=1267–1283|doi=10.1007/s00604-017-2179-2|s2cid=21308802|issn=0026-3672 |
NO is a [[gaseous signaling molecule]].<ref>{{Cite journal|last1=Liu|first1=Hongying|last2=Weng|first2=Lingyan|last3=Yang|first3=Chi|date=2017-03-28|title=A review on nanomaterial-based electrochemical sensors for H<sub>2</sub>O<sub>2</sub>, H<sub>2</sub>S and NO inside cells or released by cells|journal=Microchimica Acta|volume=184|issue=5|pages=1267–1283|doi=10.1007/s00604-017-2179-2|s2cid=21308802|issn=0026-3672}}</ref> It is a key [[vertebrate]] [[signal transduction|biological messenger]], playing a role in a variety of biological processes.<ref>Weller, Richard, [http://www.ted.com/talks/richard_weller_could_the_sun_be_good_for_your_heart.html Could the sun be good for your heart?] {{Webarchive|url=https://web.archive.org/web/20140216052804/http://www.ted.com/talks/richard_weller_could_the_sun_be_good_for_your_heart.html |date=2014-02-16 }} TedxGlasgow. Filmed March 2012, posted January 2013</ref> It is a bioproduct in almost all types of organisms, including bacteria, plants, fungi, and animal cells.<ref>Roszer, T (2012) The Biology of Subcellular Nitric Oxide. {{ISBN|978-94-007-2818-9}}</ref> |
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Nitric oxide, an [[endothelium-derived relaxing factor]] (EDRF), is biosynthesized endogenously from [[arginine|<small>L</small>-arginine]], [[oxygen]], and [[NADPH]] by various [[nitric oxide synthase]] (NOS) [[enzyme]]s.<ref name="Perez 2598–2607.e1">{{Cite journal|last1=Perez|first1=Krystle M.|last2=Laughon|first2=Matthew|date=November 2015|title=Sildenafil in Term and Premature Infants: A Systematic Review|journal=Clinical Therapeutics|volume=37|issue=11|pages=2598–2607.e1|doi=10.1016/j.clinthera.2015.07.019|pmid=26490498|issn=0149-2918}}</ref> Reduction of inorganic nitrate may also make nitric oxide.<ref name="stryer" /> One of the main enzymatic targets of nitric oxide is [[Guanylate cyclase|guanylyl cyclase]].<ref name=" |
Nitric oxide, an [[endothelium-derived relaxing factor]] (EDRF), is biosynthesized endogenously from [[arginine|<small>L</small>-arginine]], [[oxygen]], and [[NADPH]] by various [[nitric oxide synthase]] (NOS) [[enzyme]]s.<ref name="Perez 2598–2607.e1">{{Cite journal|last1=Perez|first1=Krystle M.|last2=Laughon|first2=Matthew|date=November 2015|title=Sildenafil in Term and Premature Infants: A Systematic Review|journal=Clinical Therapeutics|volume=37|issue=11|pages=2598–2607.e1|doi=10.1016/j.clinthera.2015.07.019|pmid=26490498|issn=0149-2918}}</ref> Reduction of inorganic nitrate may also make nitric oxide.<ref name="stryer" /> One of the main enzymatic targets of nitric oxide is [[Guanylate cyclase|guanylyl cyclase]].<ref name="Hancock-2010">{{Cite book|title=Cell signalling|last=T.|first=Hancock, John|date=2010|publisher=Oxford University Press|isbn=9780199232109|edition= 3rd|location=Oxford|oclc=444336556}}</ref> The binding of nitric oxide to the [[heme]] region of the enzyme leads to activation, in the presence of iron.<ref name="Hancock-2010" /> Nitric oxide is highly reactive (having a lifetime of a few seconds), yet diffuses freely across membranes. These attributes make nitric oxide ideal for a transient [[paracrine]] (between adjacent cells) and [[autocrine]] (within a single cell) signaling molecule.<ref name="stryer">{{cite book|last = Stryer| first = Lubert| title = Biochemistry |edition=4th| publisher = W.H. Freeman and Company|year = 1995| page = 732| isbn = 978-0-7167-2009-6}}</ref> Once nitric oxide is converted to nitrates and nitrites by oxygen and water, cell signaling is deactivated.<ref name="Hancock-2010" /> |
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The [[endothelium]] (inner lining) of [[blood vessel]]s uses nitric oxide to signal the surrounding [[smooth muscle]] to relax, resulting in [[vasodilation]] and increasing blood flow.<ref name="stryer" /> [[Sildenafil]] (Viagra) is a drug that uses the nitric oxide pathway. Sildenafil does not produce nitric oxide, but enhances the signals that are downstream of the nitric oxide pathway by protecting [[cyclic guanosine monophosphate]] (cGMP) from degradation by [[cGMP-specific phosphodiesterase type 5]] (PDE5) in the [[corpus cavernosum penis|corpus cavernosum]], allowing for the signal to be enhanced, and thus [[vasodilation]].<ref name="Perez 2598–2607.e1"/> Another endogenous gaseous transmitter, [[Hydrogen sulfide|hydrogen sulfide (H<sub>2</sub>S)]] works with NO to induce vasodilation and angiogenesis in a cooperative manner.<ref>{{Cite journal|last1=Szabo|first1=Csaba|last2=Coletta|first2=Ciro|last3=Chao|first3=Celia|last4=Módis|first4=Katalin|last5=Szczesny|first5=Bartosz|last6=Papapetropoulos|first6=Andreas|last7=Hellmich|first7=Mark R.|date=2013-07-23|title=Tumor-derived hydrogen sulfide, produced by cystathionine-β-synthase, stimulates bioenergetics, cell proliferation, and angiogenesis in colon cancer|journal=Proceedings of the National Academy of Sciences of the United States of America|volume=110|issue=30|pages=12474–12479|doi=10.1073/pnas.1306241110|issn=1091-6490|pmc=3725060|pmid=23836652|bibcode=2013PNAS..11012474S|doi-access=free}}</ref><ref name="Altaany 879–888">{{Cite journal|last1=Altaany|first1=Zaid|last2=Yang|first2=Guangdong|last3=Wang|first3=Rui|date=July 2013|title=Crosstalk between hydrogen sulfide and nitric oxide in endothelial cells|journal=Journal of Cellular and Molecular Medicine|volume=17|issue=7|pages=879–888|doi=10.1111/jcmm.12077|issn=1582-4934|pmc=3822893|pmid=23742697}}</ref> |
The [[endothelium]] (inner lining) of [[blood vessel]]s uses nitric oxide to signal the surrounding [[smooth muscle]] to relax, resulting in [[vasodilation]] and increasing blood flow.<ref name="stryer" /> [[Sildenafil]] (Viagra) is a drug that uses the nitric oxide pathway. Sildenafil does not produce nitric oxide, but enhances the signals that are downstream of the nitric oxide pathway by protecting [[cyclic guanosine monophosphate]] (cGMP) from degradation by [[cGMP-specific phosphodiesterase type 5]] (PDE5) in the [[corpus cavernosum penis|corpus cavernosum]], allowing for the signal to be enhanced, and thus [[vasodilation]].<ref name="Perez 2598–2607.e1"/> Another endogenous gaseous transmitter, [[Hydrogen sulfide|hydrogen sulfide (H<sub>2</sub>S)]] works with NO to induce vasodilation and angiogenesis in a cooperative manner.<ref>{{Cite journal|last1=Szabo|first1=Csaba|last2=Coletta|first2=Ciro|last3=Chao|first3=Celia|last4=Módis|first4=Katalin|last5=Szczesny|first5=Bartosz|last6=Papapetropoulos|first6=Andreas|last7=Hellmich|first7=Mark R.|date=2013-07-23|title=Tumor-derived hydrogen sulfide, produced by cystathionine-β-synthase, stimulates bioenergetics, cell proliferation, and angiogenesis in colon cancer|journal=Proceedings of the National Academy of Sciences of the United States of America|volume=110|issue=30|pages=12474–12479|doi=10.1073/pnas.1306241110|issn=1091-6490|pmc=3725060|pmid=23836652|bibcode=2013PNAS..11012474S|doi-access=free}}</ref><ref name="Altaany 879–888">{{Cite journal|last1=Altaany|first1=Zaid|last2=Yang|first2=Guangdong|last3=Wang|first3=Rui|date=July 2013|title=Crosstalk between hydrogen sulfide and nitric oxide in endothelial cells|journal=Journal of Cellular and Molecular Medicine|volume=17|issue=7|pages=879–888|doi=10.1111/jcmm.12077|issn=1582-4934|pmc=3822893|pmid=23742697}}</ref> |
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Nasal breathing produces nitric oxide within the body, while [[mouth breathing|oral breathing]] does not.<ref>{{cite journal|doi=10.2170/jjphysiol.47.465|doi-access=free|issn=0021-521X|first1=Yoshifumi|last1=Yasuda|first2=Tomonori|last2=Itoh|first3=Miharu|last3=Miyamura|first4=Hitoo|last4=Nishino|journal=Japanese Journal of Physiology|year=1997|volume=47|issue=5|url=https://www.jstage.jst.go.jp/article/jjphysiol/47/5/47_5_465/_article/-char/ja/|pages=465–470|title=Comparison of Exhaled Nitric Oxide and Cardiorespiratory Indices between Nasal and Oral Breathing during Submaximal Exercise in Humans|access-date=2022-11-17}} |
Nasal breathing produces nitric oxide within the body, while [[mouth breathing|oral breathing]] does not.<ref>{{cite journal|doi=10.2170/jjphysiol.47.465|doi-access=free|issn=0021-521X|first1=Yoshifumi|last1=Yasuda|first2=Tomonori|last2=Itoh|first3=Miharu|last3=Miyamura|first4=Hitoo|last4=Nishino|journal=Japanese Journal of Physiology|year=1997|volume=47|issue=5|url=https://www.jstage.jst.go.jp/article/jjphysiol/47/5/47_5_465/_article/-char/ja/|pages=465–470|title=Comparison of Exhaled Nitric Oxide and Cardiorespiratory Indices between Nasal and Oral Breathing during Submaximal Exercise in Humans|pmid=9504133 |access-date=2022-11-17}} |
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</ref><ref>{{Cite web|last=Dahl|first=Melissa|date=2011-01-11|title='Mouth-breathing' gross, harmful to your health|url=http://www.nbcnews.com/healthmain/mouth-breathing-gross-harmful-your-health-1C6437430 |
</ref><ref>{{Cite web|last=Dahl|first=Melissa|date=2011-01-11|title='Mouth-breathing' gross, harmful to your health|url=http://www.nbcnews.com/healthmain/mouth-breathing-gross-harmful-your-health-1C6437430|access-date=2021-09-06|website=NBC News|language=en}}</ref> |
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== Occupational safety and health == |
== Occupational safety and health == |
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== Explosion hazard == |
== Explosion hazard == |
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Liquid nitrogen oxide is very sensitive to detonation even in the absence of fuel, and can be initiated as readily as nitroglycerin. Detonation of the endothermic liquid oxide close to its b.p. (-152°C) generated a 100 kbar pulse and fragmented the test equipment. It is the simplest molecule that is capable of detonation in all three phases. The liquid oxide is sensitive and may explode during distillation, and this has been the cause of industrial accidents.<ref>{{Cite |
Liquid nitrogen oxide is very sensitive to detonation even in the absence of fuel, and can be initiated as readily as nitroglycerin. Detonation of the endothermic liquid oxide close to its b.p. (-152°C) generated a 100 kbar pulse and fragmented the test equipment. It is the simplest molecule that is capable of detonation in all three phases. The liquid oxide is sensitive and may explode during distillation, and this has been the cause of industrial accidents.<ref>{{Cite book|title=Bretherick's Handbook of Reactive Chemical Hazards {{!}} ScienceDirect|url=https://www.sciencedirect.com/book/9780081009710/brethericks-handbook-of-reactive-chemical-hazards|access-date=2022-02-23|isbn=9780081009710 |language=en |last1=Urben |first1=Peter |date=22 May 2017 |publisher=Elsevier Science }}</ref> Gaseous nitric oxide detonates at about 2300 m/s, but as a solid it can reach a detonation velocity of 6100 m/s.<ref>{{Cite journal|last1=Ribovich|first1=John|last2=Murphy|first2=John|last3=Watson|first3=Richard|date=1975-01-01|title=Detonation studies with nitric oxide, nitrous oxide, nitrogen tetroxide, carbon monoxide, and ethylene|url=https://dx.doi.org/10.1016/0304-3894%2875%2980001-X|journal=Journal of Hazardous Materials|language=en|volume=1|issue=4|pages=275–287|doi=10.1016/0304-3894(75)80001-X|bibcode=1975JHzM....1..275R |issn=0304-3894}}</ref> |
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==References== |
==References== |
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'''Notes ''' |
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{{Reflist}} |
{{Reflist}} |
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'''Further reading''' |
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* Butler A. and Nicholson R.; [https://books.google.com/books?id=0d1Z0m76YeYC |
* Butler A. and Nicholson R.; [https://books.google.com/books?id=0d1Z0m76YeYC "Life, death and NO."] Cambridge 2003. {{ISBN|978-0-85404-686-7}}. |
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* van Faassen, E. E.; Vanin, A. F. (eds); [https://books.google.com/books?id=UJ4glFNEcn0C |
* van Faassen, E. E.; Vanin, A. F. (eds); [https://books.google.com/books?id=UJ4glFNEcn0C "Radicals for life: The various forms of Nitric Oxide."] Elsevier, Amsterdam 2007. {{ISBN|978-0-444-52236-8}}. |
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* Ignarro, L. J. (ed.); [https://books.google.com/books?id=h5FugARr4bgC |
* Ignarro, L. J. (ed.); [https://books.google.com/books?id=h5FugARr4bgC "Nitric oxide:biology and pathobiology."] Academic Press, San Diego 2000. {{ISBN|0-12-370420-0}}. |
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==External links== |
==External links== |
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[[Category:Gaseous signaling molecules]] |
[[Category:Gaseous signaling molecules]] |
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[[Category:GABAA receptor positive allosteric modulators]] |
[[Category:GABAA receptor positive allosteric modulators]] |
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[[Category:Mitochondrial toxins]] |
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[[Category:Nitrogen oxides]] |
[[Category:Nitrogen oxides]] |
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[[Category:Neurotransmitters]] |
[[Category:Neurotransmitters]] |
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[[Category:Orphan drugs]] |
[[Category:Orphan drugs]] |
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[[Category:Diatomic molecules]] |
[[Category:Diatomic molecules]] |
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[[Category:Albanian discoveries]] |
Revision as of 02:52, 22 June 2024
![]() | |||
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Names | |||
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IUPAC name
Nitrogen monoxide[1]
| |||
Systematic IUPAC name
Oxidonitrogen(•)[2] (additive) | |||
Other names
Nitrogen oxide
Nitrogen(II) oxide Oxonitrogen Nitrogen monoxide | |||
Identifiers | |||
3D model (JSmol)
|
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3DMet | |||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
DrugBank | |||
ECHA InfoCard | 100.030.233 | ||
EC Number |
| ||
451 | |||
KEGG | |||
PubChem CID
|
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RTECS number |
| ||
UNII | |||
UN number | 1660 | ||
CompTox Dashboard (EPA)
|
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Properties | |||
NO | |||
Molar mass | 30.006 g·mol−1 | ||
Appearance | Colourless gas | ||
Density | 1.3402 g/L | ||
Melting point | −164 °C (−263 °F; 109 K) | ||
Boiling point | −152 °C (−242 °F; 121 K) | ||
0.0098 g / 100 ml (0 °C) 0.0056 g / 100 ml (20 °C) | |||
Refractive index (nD)
|
1.0002697 | ||
Structure | |||
linear (point group C∞v) | |||
Thermochemistry | |||
Std molar
entropy (S⦵298) |
210.76 J/(K·mol) | ||
Std enthalpy of
formation (ΔfH⦵298) |
90.29 kJ/mol | ||
Pharmacology | |||
R07AX01 (WHO) | |||
License data | |||
Inhalation | |||
Pharmacokinetics: | |||
good | |||
via pulmonary capillary bed | |||
2–6 seconds | |||
Hazards | |||
Occupational safety and health (OHS/OSH): | |||
Main hazards
|
| ||
GHS labelling: | |||
![]() ![]() ![]() ![]() | |||
Danger | |||
H270, H280, H314, H330[3][4] | |||
P220, P244, P260, P280, P303+P361+P353+P315, P304+P340+P315, P305+P351+P338+P315, P370+P376, P403, P405[3][4] | |||
NFPA 704 (fire diamond) | |||
Lethal dose or concentration (LD, LC): | |||
LC50 (median concentration)
|
315 ppm (rabbit, 15 min) 854 ppm (rat, 4 h) 2500 ppm (mouse, 12 min)[5] | ||
LCLo (lowest published)
|
320 ppm (mouse)[5] | ||
Safety data sheet (SDS) | External SDS | ||
Related compounds | |||
Related nitrogen oxides
|
Dinitrogen pentoxide Dinitrogen tetroxide | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
Nitric oxide (nitrogen oxide or nitrogen monoxide[1]) is a colorless gas with the formula NO. It is one of the principal oxides of nitrogen. Nitric oxide is a free radical: it has an unpaired electron, which is sometimes denoted by a dot in its chemical formula (•N=O or •NO). Nitric oxide is also a heteronuclear diatomic molecule, a class of molecules whose study spawned early modern theories of chemical bonding.[6]
An important intermediate in industrial chemistry, nitric oxide forms in combustion systems and can be generated by lightning in thunderstorms. In mammals, including humans, nitric oxide is a signaling molecule in many physiological and pathological processes.[7] It was proclaimed the "Molecule of the Year" in 1992.[8] The 1998 Nobel Prize in Physiology or Medicine was awarded for discovering nitric oxide's role as a cardiovascular signalling molecule.[9]
Nitric oxide should not be confused with nitrogen dioxide (NO2), a brown gas and major air pollutant, or with nitrous oxide (N2O), an anesthetic gas.[6]
Physical properties
Electronic configuration
The ground state electronic configuration of NO is, in united atom notation:[10]
The first two orbitals are actually pure atomic 1sO and 1sN from oxygen and nitrogen respectively and therefore are usually not noted in the united atom notation. Orbitals noted with an asterisk are antibonding. The ordering of 5σ and 1π according to their binding energies is subject to discussion. Removal of a 1π electron leads to 6 states whose energies span over a range starting at a lower level than a 5σ electron an extending to a higher level. This is due to the different orbital momentum couplings between a 1π and a 2π electron.
The lone electron in the 2π orbital makes NO a doublet (X ²Π) in its ground state whose degeneracy is split in the fine structure from spin-orbit coupling with a total momentum J=3⁄2 oder J=1⁄2.
Dipole
The dipole of NO has been measured experimentally to 0.15740 D and is oriented from O to N (⁻NO⁺) due to the transfer of negative electronic charge from oxygen to nitrogen. [11]
Reactions
With di- and triatomic molecules
Upon condensing to a liquid, nitric oxide dimerizes to dinitrogen dioxide, but the association is weak and reversible. The N–N distance in crystalline NO is 218 pm, nearly twice the N–O distance.[6]
Since the heat of formation of •NO is endothermic, NO can be decomposed to the elements. Catalytic converters in cars exploit this reaction:
- 2 •NO → O2 + N2
When exposed to oxygen, nitric oxide converts into nitrogen dioxide:
- 2 •NO + O2 → 2 •NO2
This reaction is thought to occur via the intermediates ONOO• and the red compound ONOONO.[12]
In water, nitric oxide reacts with oxygen to form nitrous acid (HNO2). The reaction is thought to proceed via the following stoichiometry:
- 4 •NO + O2 + 2 H2O → 4 HNO2
Nitric oxide reacts with fluorine, chlorine, and bromine to form the nitrosyl halides, such as nitrosyl chloride:
- 2 •NO + Cl2 → 2 NOCl
With NO2, also a radical, NO combines to form the intensely blue dinitrogen trioxide:[6]
- •NO + •NO2 ⇌ ON−NO2
Organic chemistry
The addition of a nitric oxide moiety to another molecule is often referred to as nitrosylation. The Traube reaction[13] is the addition of a two equivalents of nitric oxide onto an enolate, giving a diazeniumdiolate (also called a nitrosohydroxylamine).[14] The product can undergo a subsequent retro-aldol reaction, giving an overall process similar to the haloform reaction. For example, nitric oxide reacts with acetone and an alkoxide to form a diazeniumdiolate on each α position, with subsequent loss of methyl acetate as a by-product:[15]
This reaction, which was discovered around 1898, remains of interest in nitric oxide prodrug research. Nitric oxide can also react directly with sodium methoxide, ultimately forming sodium formate and nitrous oxide by way of an N-methoxydiazeniumdiolate.[16]
Coordination complexes
Nitric oxide reacts with transition metals to give complexes called metal nitrosyls. The most common bonding mode of nitric oxide is the terminal linear type (M−NO).[6] Alternatively, nitric oxide can serve as a one-electron pseudohalide. In such complexes, the M−N−O group is characterized by an angle between 120° and 140°. The NO group can also bridge between metal centers through the nitrogen atom in a variety of geometries.
Production and preparation
In commercial settings, nitric oxide is produced by the oxidation of ammonia at 750–900 °C (normally at 850 °C) with platinum as catalyst in the Ostwald process:
- 4 NH3 + 5 O2 → 4 •NO + 6 H2O
The uncatalyzed endothermic reaction of oxygen (O2) and nitrogen (N2), which is effected at high temperature (>2000 °C) by lightning has not been developed into a practical commercial synthesis (see Birkeland–Eyde process):
- N2 + O2 → 2 •NO
Laboratory methods
In the laboratory, nitric oxide is conveniently generated by reduction of dilute nitric acid with copper:
- 8 HNO3 + 3 Cu → 3 Cu(NO3)2 + 4 H2O + 2 •NO
An alternative route involves the reduction of nitrous acid in the form of sodium nitrite or potassium nitrite:
- 2 NaNO2 + 2 NaI + 2 H2SO4 → I2 + 2 Na2SO4 + 2 H2O + 2 •NO
- 2 NaNO2 + 2 FeSO4 + 3 H2SO4 → Fe2(SO4)3 + 2 NaHSO4 + 2 H2O + 2 •NO
- 3 KNO2 + KNO3 + Cr2O3 → 2 K2CrO4 + 4 •NO
The iron(II) sulfate route is simple and has been used in undergraduate laboratory experiments. So-called NONOate compounds are also used for nitric oxide generation.
Detection and assay
![](http://upload.wikimedia.org/wikipedia/commons/thumb/0/06/The_production_and_diffusion_of_nitric_oxide_%28NO%29_%28white%29_in_the_cytoplasm_%28green%29_of_clusters_of_conifer_cells_one_hour_after_mechanical_agitation.jpg/250px-The_production_and_diffusion_of_nitric_oxide_%28NO%29_%28white%29_in_the_cytoplasm_%28green%29_of_clusters_of_conifer_cells_one_hour_after_mechanical_agitation.jpg)
Nitric oxide concentration can be determined using a chemiluminescent reaction involving ozone.[17] A sample containing nitric oxide is mixed with a large quantity of ozone. The nitric oxide reacts with the ozone to produce oxygen and nitrogen dioxide, accompanied with emission of light (chemiluminescence):
- •NO + O3 → •NO2 + O2 + hν
which can be measured with a photodetector. The amount of light produced is proportional to the amount of nitric oxide in the sample.
Other methods of testing include electroanalysis (amperometric approach), where ·NO reacts with an electrode to induce a current or voltage change. The detection of NO radicals in biological tissues is particularly difficult due to the short lifetime and concentration of these radicals in tissues. One of the few practical methods is spin trapping of nitric oxide with iron-dithiocarbamate complexes and subsequent detection of the mono-nitrosyl-iron complex with electron paramagnetic resonance (EPR).[18][19]
A group of fluorescent dye indicators that are also available in acetylated form for intracellular measurements exist. The most common compound is 4,5-diaminofluorescein (DAF-2).[20]
Environmental effects
Acid rain deposition
Nitric oxide reacts with the hydroperoxyl radical (HO•
2) to form nitrogen dioxide (NO2), which then can react with a hydroxyl radical (HO•) to produce nitric acid (HNO3):
- •NO + HO•
2 → •NO2 + HO• - •NO2 + HO• → HNO3
Nitric acid, along with sulfuric acid, contributes to acid rain deposition.
Ozone depletion
•NO participates in ozone layer depletion. Nitric oxide reacts with stratospheric ozone to form O2 and nitrogen dioxide:
- •NO + O3 → •NO2 + O2
This reaction is also utilized to measure concentrations of •NO in control volumes.
Precursor to NO2
As seen in the acid deposition section, nitric oxide can transform into nitrogen dioxide (this can happen with the hydroperoxy radical, HO•
2, or diatomic oxygen, O2). Symptoms of short-term nitrogen dioxide exposure include nausea, dyspnea and headache. Long-term effects could include impaired immune and respiratory function.[21]
Biological functions
NO is a gaseous signaling molecule.[22] It is a key vertebrate biological messenger, playing a role in a variety of biological processes.[23] It is a bioproduct in almost all types of organisms, including bacteria, plants, fungi, and animal cells.[24]
Nitric oxide, an endothelium-derived relaxing factor (EDRF), is biosynthesized endogenously from L-arginine, oxygen, and NADPH by various nitric oxide synthase (NOS) enzymes.[25] Reduction of inorganic nitrate may also make nitric oxide.[26] One of the main enzymatic targets of nitric oxide is guanylyl cyclase.[27] The binding of nitric oxide to the heme region of the enzyme leads to activation, in the presence of iron.[27] Nitric oxide is highly reactive (having a lifetime of a few seconds), yet diffuses freely across membranes. These attributes make nitric oxide ideal for a transient paracrine (between adjacent cells) and autocrine (within a single cell) signaling molecule.[26] Once nitric oxide is converted to nitrates and nitrites by oxygen and water, cell signaling is deactivated.[27]
The endothelium (inner lining) of blood vessels uses nitric oxide to signal the surrounding smooth muscle to relax, resulting in vasodilation and increasing blood flow.[26] Sildenafil (Viagra) is a drug that uses the nitric oxide pathway. Sildenafil does not produce nitric oxide, but enhances the signals that are downstream of the nitric oxide pathway by protecting cyclic guanosine monophosphate (cGMP) from degradation by cGMP-specific phosphodiesterase type 5 (PDE5) in the corpus cavernosum, allowing for the signal to be enhanced, and thus vasodilation.[25] Another endogenous gaseous transmitter, hydrogen sulfide (H2S) works with NO to induce vasodilation and angiogenesis in a cooperative manner.[28][29]
Nasal breathing produces nitric oxide within the body, while oral breathing does not.[30][31]
Occupational safety and health
In the U.S., the Occupational Safety and Health Administration (OSHA) has set the legal limit (permissible exposure limit) for nitric oxide exposure in the workplace as 25 ppm (30 mg/m3) over an 8-hour workday. The National Institute for Occupational Safety and Health (NIOSH) has set a recommended exposure limit (REL) of 25 ppm (30 mg/m3) over an 8-hour workday. At levels of 100 ppm, nitric oxide is immediately dangerous to life and health.[32]
Explosion hazard
Liquid nitrogen oxide is very sensitive to detonation even in the absence of fuel, and can be initiated as readily as nitroglycerin. Detonation of the endothermic liquid oxide close to its b.p. (-152°C) generated a 100 kbar pulse and fragmented the test equipment. It is the simplest molecule that is capable of detonation in all three phases. The liquid oxide is sensitive and may explode during distillation, and this has been the cause of industrial accidents.[33] Gaseous nitric oxide detonates at about 2300 m/s, but as a solid it can reach a detonation velocity of 6100 m/s.[34]
References
Notes
- ^ a b Nomenclature of Inorganic Chemistry, IUPAC Recommendations (PDF). International Union of Pure and Applied Chemistry. 2005. p. 69.
- ^ "Nitric Oxide (CHEBI:16480)". Chemical Entities of Biological Interest (ChEBI). UK: European Bioinformatics Institute.
- ^ a b c "Nitrogen monoxide - Registration Dossier - ECHA". Retrieved 2020-11-02.
- ^ a b c d "Safety Data Sheet - Nitric Oxide, compressed - Registration Dossier" (PDF). Retrieved 2020-11-02.
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Further reading
- Butler A. and Nicholson R.; "Life, death and NO." Cambridge 2003. ISBN 978-0-85404-686-7.
- van Faassen, E. E.; Vanin, A. F. (eds); "Radicals for life: The various forms of Nitric Oxide." Elsevier, Amsterdam 2007. ISBN 978-0-444-52236-8.
- Ignarro, L. J. (ed.); "Nitric oxide:biology and pathobiology." Academic Press, San Diego 2000. ISBN 0-12-370420-0.
External links
- International Chemical Safety Card 1311
- "Nitric oxide and its role in health and diabetes". 21 October 2015.
- Microscale Gas Chemistry: Experiments with Nitrogen Oxides
- Your Brain Boots Up Like a Computer – new insights about the biological role of nitric oxide.
- Assessing The Potential of Nitric Oxide in the Diabetic Foot
- New Discoveries About Nitric Oxide Can Provide Drugs For Schizophrenia
- Nitric Oxide at the Chemical Database
- "Immediately Dangerous to Life or Health Concentrations (IDLH): Nitric oxide". National Institute for Occupational Safety and Health. 2 November 2018.