Carbon monoxide
Preferred IUPAC name Carbon monoxide
Other names Carbon monooxide Carbonous oxide Carbon(II) oxide Carbonyl
Identifiers
CAS number	630-08-0 Y
PubChem	281 Y
ChemSpider	275 Y
UNII	7U1EE4V452 Y
EC number	211-128-3
UN number	1016
KEGG	D09706 Y
MeSH	Carbon+monoxide
ChEBI	CHEBI:17245 Y
RTECS number	FG3500000
Beilstein Reference	3587264
Gmelin Reference	421
Jmol-3D images	Image 1
SMILES [C-]#[O+]
InChI InChI=1S/CO/c1-2 Y Key: UGFAIRIUMAVXCW-UHFFFAOYSA-N Y InChI=1/CO/c1-2 Key: UGFAIRIUMAVXCW-UHFFFAOYAT
Properties
Molecular formula	CO
Molar mass	28.010 g/mol
Appearance	colourless gas
Odor	odorless
Density	789 kg/m3, liquid 1.250 kg/m3 at 0 °C, 1 atm 1.145 kg/m3 at 25 °C, 1 atm
Melting point	−205.02 °C, 68 K, -337 °F
Boiling point	−191.5 °C, 82 K, -313 °F
Solubility in water	27.6 mg/1 L (25 °C)
Solubility	soluble in chloroform, acetic acid, ethyl acetate, ethanol, ammonium hydroxide, benzene
Refractive index (nD)	1.0003364
Dipole moment	0.122 D
Thermochemistry
Std enthalpy of formation ΔfHo298	−110.5 kJ·mol−1
Standard molar entropy So298	198 J·mol−1·K−1
Hazards
MSDS	External MSDS
EU Index	006-001-00-2
EU classification	Highly flammable (F+) Very toxic (T+)
R-phrases	R61 R12 R26 R48/23
S-phrases	S53 S45
NFPA 704	4 4 2
Flash point	−191 °C (82.2 K; −311.8 °F)
Autoignition temperature	609 °C (882 K; 1,128 °F)
Related compounds
Related carbon oxides	Carbon dioxide Carbon suboxide Oxocarbons
Supplementary data page
Structure and properties	n, εr, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Carbon monoxide (CO), also called carbonous oxide, is a colorless, odorless, and tasteless gas that is slightly lighter than air. It can be toxic to humans and animals when encountered in higher concentrations, although it is also produced in normal animal metabolism in low quantities, and is thought to have some normal biological functions. In the atmosphere however, it is short lived and spatially variable, since it combines with oxygen to form carbon dioxide and ozone.

Carbon monoxide consists of one carbon atom and one oxygen atom, connected by a triple bond that consists of two covalent bonds as well as one dative covalent bond. It is the simplest oxocarbon, and isoelectronic with the cyanide ion and molecular nitrogen. In coordination complexes the carbon monoxide ligand is called carbonyl.

Carbon monoxide is produced from the partial oxidation of carbon-containing compounds; it forms when there is not enough oxygen to produce carbon dioxide (CO₂), such as when operating a stove or an internal combustion engine in an enclosed space. In the presence of oxygen, carbon monoxide burns with a blue flame, producing carbon dioxide.^[1] Coal gas, which was widely used before the 1960s for domestic lighting, cooking, and heating, had carbon monoxide as a significant constituent. Some processes in modern technology, such as iron smelting, still produce carbon monoxide as a byproduct.^[2]

Worldwide, the largest source of carbon monoxide is natural in origin, due to photochemical reactions in the troposphere that generate about 5 x 10¹² kilograms per year.^[3] Other natural sources of CO include volcanoes, forest fires, and other forms of combustion.

In biology, carbon monoxide is naturally produced by the action of heme oxygenase 1 and 2 on the heme from hemoglobin breakdown. This process produces a certain amount of carboxyhemoglobin in normal persons, even if they do not breathe any carbon monoxide. Following the first report that carbon monoxide is a normal neurotransmitter in 1993,^[4] as well as one of three gases that naturally modulate inflammatory responses in the body (the other two being nitric oxide and hydrogen sulfide), carbon monoxide has received a great deal of clinical attention as a biological regulator. In many tissues, all three gases are known to act as anti-inflammatories, vasodilators, and promoters of neovascular growth.^[5] Clinical trials of small amounts of carbon monoxide as a drug are on-going.

History[link]

That burning coals emanated toxic fumes was first recorded by Aristotle (384–322 BC). An ancient method of execution was to shut the criminal in a bathing room with smouldering coals. What was not known was the mechanism of death. Galen (129–199 AD) speculated that there was a change in the composition of the air which caused harm when inhaled.^[6] In 1776, the French chemist de Lassone produced CO by heating zinc oxide with coke, but mistakenly concluded that the gaseous product was hydrogen, as it burned with a blue flame. The gas was identified as a compound containing carbon and oxygen by the Scottish chemist William Cumberland Cruikshank in the year 1800. Its toxic properties on dogs were thoroughly investigated by Claude Bernard around 1846.^[7]

During World War II, a gas mixture including carbon monoxide was used to keep motor vehicles running in parts of the world where gasoline and diesel fuel were scarce. External (with few exceptions) charcoal or wood gas generators were fitted, and the mixture of atmospheric nitrogen, carbon monoxide, and smaller amounts of other gases produced by gasification was piped to a gas mixer. The gas mixture produced by this process is known as wood gas. Carbon monoxide was also, it was reported, used on a small scale during the Holocaust at some Nazi extermination camps, the most notable by gas vans in Chelmno, and in the Action T4 "euthanasia" program.^[8]

Molecular properties[link]

Carbon monoxide has a molar mass of 28.0, which makes it slightly lighter than air, whose average molar mass is 28.8. According to the ideal gas law, CO is therefore less dense than air. Neither gas is "ideal", however, so neither exactly has the densities predicted by the ideal gas law.

The bond length between the carbon atom and the oxygen atom is 112.8 pm.^[9][10] This bond length is consistent with a triple bond, as in molecular nitrogen (N₂), which has a similar bond length and nearly the same molecular mass. Carbon-oxygen double bonds are significantly longer, 120.8 pm in formaldehyde, for example.^[11] The boiling point (82 K) and melting point (68 K) are very similar to those of N₂ (77 K and 63 K, respectively). The bond dissociation energy of 1072 kJ/mol is stronger than that of N₂ (942 kJ/mol) and represents the strongest chemical bond known.^[12]

The ground electronic state of carbon monoxide is a singlet state^[13] since there are no unpaired electrons.

Bonding and dipole moment[link]

Carbon and oxygen together have a total of 10 valence electrons in carbon monoxide. To satisfy the octet rule for the carbon, the two atoms form a triple bond, with six shared electrons in three bonding molecular orbitals, rather than the usual double bond found in organic carbonyl compounds. Since four of the shared electrons come from the oxygen atom and only two from carbon, one of the bonding orbitals is occupied by two electrons from oxygen, forming a dative or dipolar bond. This causes a polarization of the molecule, with a small negative charge on carbon and a small positive charge on oxygen. The other two bonding orbitals are each occupied by one electron from carbon and one from oxygen, forming (polar) covalent bonds, and a reverse polarization is produced by the greater electronegativity of oxygen, with a small negative charge on oxygen. In the free carbon monoxide, a net negative charge δ- remains at the carbon end and the molecule has a small dipole moment of 0.122 D.^[14]

Oxygen has more electron density, but also more positive charge. Because most electron density is located between the atoms, the molecule has a net positive charge on the oxygen end. By contrast, the isoelectronic dinitrogen molecule has no dipole moment.

If carbon monoxide acts as a ligand, the polarity of the dipole may reverse with a net negative charge on the oxygen end, depending on the structure of the coordination complex.^[15] See also the section "Coordination chemistry" below.

Resonance structures and oxidation state[link]

Resonance structures of carbon monoxide

Different (correct) Lewis structures can be drawn for carbon monoxide. In the structure with three covalent bonds, the octet rule is satisfied, but the electropositive carbon has a negative formal charge. The structure with two covalent bonds would be consistent with the very low dipole moment of the molecule if the bonds were nonpolar. The structure with one covalent bond expresses the greater electronegativity of oxygen and the calculated net atomic charges. None of them do exactly meet the real electronic structure. Calculations with natural bond orbitals show that the structure with a triple bond is the most important Lewis structure (for the free molecule); this structure is the best approximation of the real distribution of electron density, with maximal occupation of bonding orbitals and lone pair orbitals.^[16] This is in accordance with other theoretical and experimental studies that show that, despite the greater electronegativity of oxygen, the dipole moment points from the more-negative carbon end to the more-positive oxygen end.^[17][18] The three bonds, however, are in fact polar covalent bonds that are strongly polarized. The calculated polarization toward the oxygen atom is 71 % for the σ-bond and 77 % for both π-bonds.^[16] The oxidation state of carbon in carbon monoxide is +2 in each of these structures. It is calculated by counting all the bonding electrons as belonging to the more electronegative oxygen. Only the two non-bonding electrons on carbon are assigned to carbon. In this count, carbon then has only two valence electrons in the molecule compared to four in the free atom.

Biological and physiological properties[link]

[edit] Toxicity

Carbon monoxide poisoning is the most common type of fatal air poisoning in many countries.^[19] Carbon monoxide is colourless, odorless, and tasteless, but highly toxic. It combines with hemoglobin to produce carboxyhemoglobin, which is ineffective for delivering oxygen to bodily tissues. Concentrations as low as 667 ppm may cause up to 50% of the body's hemoglobin to convert to carboxyhemoglobin.^[20] A level of 50% carboxyhemoglobin may result in seizure, coma, and fatality. In the United States, the OSHA limits long-term workplace exposure levels above 50 ppm.^[21] Within short time scales, carbon monoxide absorption is cumulative, since the half-life is about 5 h in fresh air (see main article).

The most common symptoms of carbon monoxide poisoning may resemble other types of poisonings and infections, including symptoms such as headache, nausea, vomiting, dizziness, fatigue, and a feeling of weakness. Affected families often believe they are victims of food poisoning. Infants may be irritable and feed poorly. Neurological signs include confusion, disorientation, visual disturbance, syncope and seizures.^[22]

Some descriptions of carbon monoxide poisoning include retinal hemorrhages, and an abnormal cherry-red blood hue.^[23] In most clinical diagnoses these signs are seldom noticed.^[22] One difficulty with the usefulness of this cherry-red effect is that it corrects, or masks, what would otherwise be an unhealthy appearance, since the chief effect of removing deoxygenated hemoglobin is to make an asphyxiated person appear more normal, or a dead person appear more life-like, similar to the effect of red colorants in embalming fluid. The "false" or unphysiologic red-coloring effect in anoxic CO-poisoned tissue is related to the meat-coloring commercial use of carbon monoxide, discussed below.

Carbon monoxide binds to other molecules such as myoglobin and mitochondrial cytochrome oxidase. Exposures to carbon monoxide may cause significant damage to the heart and central nervous system, especially to the globus pallidus,^[24] often with long-term sequelae. Carbon monoxide may have severe adverse effects on the fetus of a pregnant woman.^[25]

Normal human physiology[link]

Carbon monoxide is produced naturally by the human body as a signaling molecule. Thus, carbon monoxide may have a physiological role in the body, such as a neurotransmitter or a blood vessel relaxant.^[26] Because of carbon monoxide's role in the body, abnormalities in its metabolism have been linked to a variety of diseases, including neurodegenerations, hypertension, heart failure, and inflammation.^[26]

Microbiology[link]

Carbon monoxide is a nutrient for methanogenic bacteria,^[27] a building-block for acetylcoenzyme A. This is the theme for the emerging field of bioorganometallic chemistry. Extremophile micro-organisms can, thus, metabolise carbon monoxide in such locations as the thermal vents of volcanoes.^[28] In bacteria, carbon monoxide is produced via the reduction of carbon dioxide by the enzyme carbon monoxide dehydrogenase, an Fe-Ni-S-containing protein.^[29]

CooA is a carbon monoxide sensor protein.^[30] The scope of its biological role is still unknown; it may be part of a signaling pathway in bacteria and archaea. Its occurrence in mammals is not established.

Occurrence[link]

Carbon monoxide occurs in various natural and artificial environments. Typical concentrations in parts per million are as follows:

Atmospheric presence[link]

The streak of red, orange, and yellow across South America, Africa, and the Atlantic Ocean in this animation points to high levels of carbon monoxide on September 30, 2005.

MOPITT 2000 global carbon monoxide.

Carbon monoxide is present in small amounts in the atmosphere, chiefly as a product of volcanic activity but also from natural and man-made fires (such as forest and bushfires, burning of crop residues, and sugarcane fire-cleaning). The burning of fossil fuels also contributes to carbon monoxide production. Carbon monoxide occurs dissolved in molten volcanic rock at high pressures in the Earth's mantle.^[37] Because natural sources of carbon monoxide are so variable from year to year, it is extremely difficult to accurately measure natural emissions of the gas.

Carbon monoxide has an indirect radiative forcing effect by elevating concentrations of methane and tropospheric ozone through chemical reactions with other atmospheric constituents (e.g., the hydroxyl radical, OH^.) that would otherwise destroy them.^[38] Through natural processes in the atmosphere, it is eventually oxidized to carbon dioxide. Carbon monoxide concentrations are both short-lived in the atmosphere and spatially variable.

In the atmosphere of Venus carbon monoxide occurs as a result of the photodissociation of carbon dioxide by electromagnetic radiation of wavelengths shorter than 169 nm.

Urban pollution[link]

Carbon monoxide is a temporary atmospheric pollutant in some urban areas, chiefly from the exhaust of internal combustion engines (including vehicles, portable and back-up generators, lawn mowers, power washers, etc.), but also from incomplete combustion of various other fuels (including wood, coal, charcoal, oil, paraffin, propane, natural gas, and trash).

Role in ground level ozone formation[link]

Carbon monoxide is part of the series of cycles of chemical reactions that form Photochemical smog. Along with aldehydes, it reacts photochemically to produce peroxy radicals. Peroxy radicals subsequently oxidize nitrogen oxide (NO) to nitrogen dioxide(NO₂).^[39] Although this creation of NO₂ is the critical step leading to low level ozone formation, it also increases this ozone in another, somewhat mutually exclusive way, by reducing the quantity of NO that is available to react with ozone.^[39]

Simplified, the net effect of the ozone cycle is:

CO + 2O₂ → CO₂ + O₃

Indoor pollution[link]

In closed environments, the concentration of carbon monoxide can easily rise to lethal levels. On average, 170 people in the United States die every year from carbon monoxide produced by non-automotive consumer products.^[40] However, according to the Florida Department of Health, "every year more than 500 Americans die from accidental exposure to carbon monoxide and thousands more across the U.S. require emergency medical care for non-fatal carbon monoxide poisoning" ^[41] These products include malfunctioning fuel-burning appliances such as furnaces, ranges, water heaters, and gas and kerosene room heaters; engine-powered equipment such as portable generators; fireplaces; and charcoal that is burned in homes and other enclosed areas. The American Association of Poison Control Centers (AAPCC) reported 15,769 cases of carbon monoxide poisoning resulting in 39 deaths in 2007.^[42] In 2005, the CPSC reported 94 generator-related carbon monoxide poisoning deaths.^[40] Forty-seven of these deaths were known to have occurred during power outages due to severe weather, including Hurricane Katrina.^[40] Still others die from carbon monoxide produced by non-consumer products, such as cars left running in attached garages. The Centers for Disease Control and Prevention estimates that several thousand people go to hospital emergency rooms every year to be treated for carbon monoxide poisoning.^[43]

Carbon monoxide is also a minor constituent of tobacco smoke.

Blood presence[link]

Carbon monoxide is absorbed through breathing and enters the blood stream through gas exchange in the lungs. Normal circulating levels in the blood are 0% to 3%, and are higher in smokers. Carbon monoxide levels cannot be assessed through a physical exam. Laboratory testing requires a blood sample (arterial or venous) and laboratory analysis on a CO-Oximeter. Additionally, a noninvasive carboxyhemoglobin (SpCO) test method from Pulse CO-Oximetry exists and has been validated compared to invasive methods.^[44]

Astrophysics[link]

Outside of Earth, carbon monoxide is the second-most common molecule in the interstellar medium, after molecular hydrogen. Because of its asymmetry, the carbon monoxide molecule produces far brighter spectral lines than the hydrogen molecule, making CO much easier to detect. Interstellar CO was first detected with radio telescopes in 1970. It is now the most commonly used tracer of molecular gas in general in the interstellar medium of galaxies, as molecular hydrogen can only be detected using ultraviolet light which requires space telescopes. Carbon monoxide observations provide much of our information about the molecular clouds in which most stars form.^[45]

Production[link]

Many methods have been developed for carbon monoxide's production.^[46]

Industrial production[link]

A major industrial source of CO is producer gas, a mixture containing mostly carbon monoxide and nitrogen, formed by combustion of carbon in air at high temperature when there is an excess of carbon. In an oven, air is passed through a bed of coke. The initially produced CO₂ equilibrates with the remaining hot carbon to give CO. The reaction of O₂ with carbon to give CO is described as the Boudouard equilibrium. Above 800 °C, CO is the predominant product:

O₂ + 2 C → 2 CO (ΔH = −221 kJ/mol)

Another source is "water gas", a mixture of hydrogen and carbon monoxide produced via the endothermic reaction of steam and carbon:

H₂O + C → H₂ + CO (ΔH = +131 kJ/mol)

Other similar "synthesis gases" can be obtained from natural gas and other fuels.

Carbon monoxide is also a byproduct of the reduction of metal oxide ores with carbon, shown in a simplified form as follows:

MO + C → M + CO

Since CO is a gas, the reduction process can be driven by heating, exploiting the positive (favorable) entropy of reaction. The Ellingham diagram shows that CO formation is favored over CO₂ in high temperatures.

Laboratory preparation[link]

Carbon monoxide is conveniently produced in the laboratory by the dehydration of formic acid, for example with sulfuric acid.^[47][48] Another method is heating an intimate mixture of powdered zinc metal and calcium carbonate, which releases CO and leaves behind zinc oxide and calcium oxide:

Zn + CaCO₃ → ZnO + CaO + CO

Coordination chemistry[link]

The HOMO of CO is a σ MO.

The LUMO of CO is a π*antibonding MO.

Most metals form coordination complexes containing covalently attached carbon monoxide. Only metals in lower oxidation states will complex with carbon monoxide ligands. This is because there must be sufficient electron density to facilitate back-donation from the metal d_xz-orbital, to the π*molecular orbital from CO. The lone pair on the carbon atom in CO, also donates electron density to the d_x²−y² on the metal to form a sigma bond. This electron donation is also exhibited with the cis effect, or the labilization of CO ligands in the cis position. In nickel carbonyl, Ni(CO)₄ forms by the direct combination of carbon monoxide and nickel metal at room temperature. For this reason, nickel in any tubing or part must not come into prolonged contact with carbon monoxide (corrosion). Nickel carbonyl decomposes readily back to Ni and CO upon contact with hot surfaces, and this method is used for the industrial purification of nickel in the Mond process.^[49]

In nickel carbonyl and other carbonyls, the electron pair on the carbon interacts with the metal; the carbon monoxide donates the electron pair to the metal. In these situations, carbon monoxide is called the carbonyl ligand. One of the most important metal carbonyls is iron pentacarbonyl, Fe(CO)₅:

Many metal-CO complexes are prepared by decarbonylation of organic solvents, not from CO. For instance, iridium trichloride and triphenylphosphine react in boiling 2-methoxyethanol or DMF) to afford IrCl(CO)(PPh₃)₂.

Metal carbonyls in coordination chemistry are usually studied using infrared spectroscopy.

Organic and main group chemistry[link]

In the presence of strong acids and water, carbon monoxide reacts with alkenes to form carboxylic acids in a process known as the Koch–Haaf reaction.^[47] In the Gattermann-Koch reaction, arenes are converted to benzaldehyde derivatives in the presence of AlCl₃ and HCl.^[48] Organolithium compounds (e.g. butyl lithium) react with carbon monoxide, but these reactions have little scientific use.

Although CO reacts with carbocations and carbanions, it is relatively nonreactive toward organic compounds without the intervention of metal catalysts.^[50]

With main group reagents, CO undergoes several noteworthy reactions. Chlorination of CO is the industrial route to the important compound phosgene. With borane CO forms an adduct, H₃BCO, which is isoelectronic with the acylium cation [H₃CCO]⁺. CO reacts with sodium to give products resulting from C-C coupling such as sodium acetylenediolate 2Na⁺·C₂O2−
2. It reacts with molten potassium to give a mixture of an organometallic compound, potassium acetylenediolate 2K⁺·C₂O2−
2, potassium benzenehexolate 6K⁺ C₆O6−
6,^[51] and potassium rhodizonate 2K⁺·C₆O2−
6.^[52]

The compounds cyclohexanehexone or triquinoyl (C₆O₆) and cyclopentanepentone or leuconic acid (C₅O₅), which so far have been obtained only in trace amounts, can be regarded as polymers of carbon monoxide.

At pressures of over 5 gigapascals, carbon monoxide disproportionates into carbon dioxide (CO₂) and a solid polymer of carbon and oxygen, in 3:2 atomic ratio.^[53][54]

Uses[link]

Chemical industry[link]

Carbon monoxide is an industrial gas that has many applications in bulk chemicals manufacturing.^[55]

Large quantities of aldehydes are produced by the hydroformylation reaction of alkenes, carbon monoxide, and H₂. Hydroformylation is coupled to the Shell Higher Olefin Process to give precursors to detergents. Methanol is produced by the hydrogenation of carbon monoxide. In a related reaction, the hydrogenation of carbon monoxide is coupled to C-C bond formation, as in the Fischer-Tropsch process where carbon monoxide is hydrogenated to liquid hydrocarbon fuels. This technology allows coal or biomass to be converted to diesel.

In the Monsanto process, carbon monoxide and methanol react in the presence of a homogeneous rhodium catalyst and hydroiodic acid to give acetic acid. This process is responsible for most of the industrial production of acetic acid.

An industrial scale use for pure carbon monoxide is purifying nickel in the Mond process.

Meat coloring[link]

Carbon monoxide is used in modified atmosphere packaging systems in the US, mainly with fresh meat products such as beef, pork, and fish to keep them looking fresh. The carbon monoxide combines with myoglobin to form carboxymyoglobin, a bright-cherry-red pigment. Carboxymyoglobin is more stable than the oxygenated form of myoglobin, oxymyoglobin, which can become oxidized to the brown pigment metmyoglobin. This stable red color can persist much longer than in normally packaged meat.^[56] Typical levels of carbon monoxide used in the facilities that use this process are between 0.4% to 0.5%.

The technology was first given "generally recognized as safe" (GRAS) status by the U.S. Food and Drug Administration (FDA) in 2002 for use as a secondary packaging system, and does not require labeling. In 2004 the FDA approved CO as primary packaging method, declaring that CO does not mask spoilage odor.^[57] Despite this ruling, the process remains controversial for fears that it masks spoilage.^[58] In 2007 a bill^[59] was introduced to the United States House of Representatives to label modified atmosphere carbon monoxide packaging as a color additive, but the bill died in subcommittee. The process is banned in many other countries, including Canada, Japan, Singapore, and the European Union.^[60][61][62]

Medicine[link]

In biology, carbon monoxide is naturally produced by the action of heme oxygenase 1 and 2 on the heme from hemoglobin breakdown. This process produces a certain amount of carboxyhemoglobin in normal persons, even if they do not breathe any carbon monoxide.

Following the first report that carbon monoxide is a normal neurotransmitter in 1993,^[4] as well as one of three gases that naturally modulate inflammatory responses in the body (the other two being nitric oxide and hydrogen sulfide), carbon monoxide has received a great deal of clinical attention as a biological regulator. In many tissues, all three gases are known to act as anti-inflammatories, vasodilators, and encouragers of neovascular growth.^[5] However, the issues are complex, as neovascular growth is not always beneficial, since it plays a role in tumor growth, and also the damage from wet macular degeneration, a disease for which smoking (a major source of carbon monoxide in the blood, several times more than natural production) increases the risk from 4 to 6 times.

There is a theory that, in some nerve cell synapses, when long-term memories are being laid down, the receiving cell makes carbon monoxide, which back-transmits to the transmitting cell, telling it to transmit more readily in future. Some such nerve cells have been shown to contain guanylate cyclase, an enzyme that is activated by carbon monoxide.^[4]

Studies involving carbon monoxide have been conducted in many laboratories throughout the world for its anti-inflammatory and cytoprotective properties. These properties have potential to be used to prevent the development of a series of pathological conditions including ischemia reperfusion injury, transplant rejection, atherosclerosis, severe sepsis, severe malaria, or autoimmunity. Clinical tests involving humans have been performed, however the results have not yet been released.^[63]

See also[link]

• Metal carbonyl
• Boudouard reaction
• Carbon monoxide (data page)
• Carbon monoxide breath monitor
• Carbon monoxide detector
• Carbon monoxide poisoning
• Criteria air contaminants
• List of highly toxic gases
• Molecular cloud
• Undersea and Hyperbaric Medical Society – hyperbaric treatment for CO poisoning
• Rubicon Foundation research articles on CO poisoning
• Guanylate cyclase
• Bridging carbonyl

References[link]

External links[link]

Wikimedia Commons has media related to: Carbon monoxide

• Explanation of the structure
• Carbon Monoxide Safety Association
• International Chemical Safety Card 0023
• National Pollutant Inventory – Carbon Monoxide
• NIOSH Pocket Guide to Chemical Hazards
• CID 281 from PubChem
• External MSDS data sheet
• Carbon Monoxide Detector Placement
• Carbon Monoxide Kills Awareness Campaign Site
• Carbon Monoxide Purification Process
• Carbon Monoxide Hazards with Backpacking Stoves
• USFDA IMPORT BULLETIN 16B-95, May 1999
• FDA Agency Response Letter GRAS Notice No. GRN 000083
• Microscale Gas Chemistry Experiments with Carbon Monoxide
• Instant insight outlining the physiology of carbon monoxide from the Royal Society of Chemistry
• Pictures of CO Poisoning Radiology and Pathology Images from MedPix.

Regina Spektor
Regina Spektor playing an electronic piano in 2006
Background information
Native name	Реги́нa Ильи́нична Спе́ктор
Born	(1980-02-18) February 18, 1980 (age 32) Moscow, Russian SFSR, Soviet Union
Origin	New York, U.S.
Genres	Anti-folk, indie rock, baroque pop, blues, pop
Occupations	Singer, songwriter, record producer
Instruments	Piano, vocals, guitar, bass guitar
Years active	1999–present
Labels	Sire/Warner Bros. Records
Associated acts	Sondre Lerche, Ben Folds, Kill Kenada, the Strokes, Dufus
Website	http://www.reginaspektor.com
Notable instruments
Steinway & Sons piano Epiphone Wildkat guitar Regina Spektor's Autograph

Regina Ilyinichna Spektor (Russian: Реги́нa Ильи́нична Спе́ктор, IPA: [rʲɪˈɡʲinə ˈspʲɛktər], English: /rɨˈdʒiːnə ˈspɛktər/; born February 18, 1980) is an American singer-songwriter and pianist. Her music is associated with the anti-folk scene centered in New York City's East Village.

Early life[link]

Spektor was born in Moscow, Soviet Union in 1980 to a musical Russian Jewish family. Her father, Ilya Spektor, is a photographer and amateur violinist. Her mother, Bella Spektor, was a music professor in a Soviet college of music and now teaches at a public elementary school in Mount Vernon, New York.^[1] She has a brother Barry (Bear), who was featured in track 7, "* * *", or "Whisper", of her 2004 album, Soviet Kitsch.

She learned how to play piano by practising on a Petrof upright that was given to her mother by her grandfather.^[2] She was also exposed to the music of rock and roll bands such as The Beatles, Queen, and The Moody Blues by her father, who obtained such recordings in Eastern Europe and traded cassettes with friends in the Soviet Union.^[1] The family left the Soviet Union in 1989, when Regina was nine and a half, during the period of Perestroika, when Soviet citizens were permitted to emigrate. Regina had to leave her piano behind.^[3] The seriousness of her piano studies led her parents to consider not leaving the USSR, but they finally decided to emigrate, due to the ethnic and political discrimination that Jews faced.^[4] Spektor is fluent in Russian and reads Hebrew, and has since paid tribute to her Russian heritage, quoting the poem February by the Russian poet Boris Pasternak in her song Après Moi, and stating “I’m very connected to the language and the culture.”^[5]

Traveling first to Austria and then Italy, the family was admitted to the United States as refugees with the assistance of HIAS (the Hebrew Immigrant Aid Society) and settled in The Bronx, where Spektor graduated from the SAR Academy, a Jewish day middle school in the Riverdale section of the Bronx. She then attended high school for two years at the Frisch School, a yeshiva in Paramus, New Jersey, but transferred to a public school, Fair Lawn High School, in Fair Lawn, New Jersey, where she finished the last two years of her high school education.^[6]

Career[link]

In New York, Spektor studied classical piano with Sonia Vargas, a professor at the Manhattan School of Music, until she was 17; Spektor's father had met Vargas through her husband, violinist Samuel Marder.^[7] Although the family had been unable to bring their piano from Russia, Spektor found a piano on which to play in the basement of her synagogue, and also practiced on tabletops and other hard surfaces.

Spektor was originally interested only in classical music, but later became interested in hip hop, rock and punk as well.^[1] Although she had always made up songs around the house, Spektor first became interested in more formal songwriting during a visit to Israel with the Nesiya Institute in her teenage years when she attracted attention from the other children on the trip for the songs she made up while hiking and realized she had an aptitude for songwriting.^[4]

Following this trip, she was exposed to the work of Joni Mitchell, Ani DiFranco, and other singer-songwriters, which encouraged her belief that she could create her own songs.^[4] She wrote her first a cappella songs around the age of 16 and her first songs for voice and piano when she was nearly 18.^[1]

Spektor completed the four-year studio composition program of the Conservatory of Music at Purchase College within three years, graduating with honors in 2001. Around this time, she also worked briefly at a butterfly farm in Luck, Wisconsin,^[8] and studied in Tottenham, ( a suburb of London) for one semester ^[9].

She gradually achieved recognition through performances in the anti-folk scene in downtown New York City, often as a duo with drummer Anders Griffen, and most importantly at the East Village's Sidewalk Cafe, but also at the Living Room, Tonic, Fez, the Knitting Factory, and CB's Gallery.^{[citation needed]} She also performed at local colleges (such as Sarah Lawrence College) with other musicians, including the Trachtenburg Family Slideshow Players. She sold self-published CDs at her performances during this period: 11:11 (2001) and Songs (2002). In 2004, she signed a contract with Warner Brothers' record label Sire Records to publish and distribute her third album Soviet Kitsch, originally self-released in 2003.

Spektor is married to Jack Dishel, guitarist with the band The Moldy Peaches.^[9]

Style[link]

Regina Spektor in concert, April 2007.

Spektor has said that she has created a great number of songs,^[10] but that she rarely writes any of them down. She has also stated that she never aspired to write songs herself, but songs seem to just flow to her.^[11] Spektor's songs are not usually autobiographical, but rather are based on scenarios and characters drawn from her imagination.^[4][12] Her songs show influences from folk,^[13][14] punk, rock, Jewish,^[12][15] Russian,^[12] hip hop,^[13][16][17] jazz,^[13][16] and classical music.^[12][16] Spektor has said that she works hard to ensure that each of her songs has its own musical style, rather than trying to develop a distinctive style for her music as a whole.^[11]

It doesn't feel natural for me to write some diary type song. I want to write a classic like Yesterday but weird songs about meatballs in refrigerators come into my head - I can't help it.^[18]

Spektor has a broad vocal range and uses the full extent of it. She also explores a variety of different and somewhat unorthodox vocal techniques, such as verses composed entirely of buzzing noises made with the lips and beatbox-style flourishes in the middle of ballads, and also makes use of such unusual musical techniques as using a drum stick to tap rhythms on the body of the piano or chair.^[4][19] Part of her style also results from the exaggeration of certain aspects of vocalization, most notably the glottal stop, which is prominent in the single "Fidelity". She also uses a strong New York accent on some words, which she has said is due to her love of New York and its culture.^[1]

Her lyrics are equally eclectic, often taking the form of abstract narratives or first-person character studies, similar to short stories or vignettes put to song.^[1][19] Spektor usually sings in English, though she sometimes includes a few words or verses of Latin, Russian, French, and other languages in her songs. She also plays with pronunciations, which she said on a NPR interview to be a remnant of her early years when she listened to pop in English without understanding the lyrics. Some of Spektor's lyrics include literary allusions,^[4] such as to F. Scott Fitzgerald and Ernest Hemingway in "Poor Little Rich Boy", The Little Prince in "Baobabs", Virginia Woolf and Margaret Atwood in "Paris", Ezra Pound and William Shakespeare in "Pound of Flesh", Shakespeare's Hamlet in "The Virgin Queen", Boris Pasternak in "Après Moi", Samson and Delilah in "Samson", and Oedipus the King in "Oedipus", Billie Holiday in "Lady" and Edith Wharton's Ethan Frome in "2.99 cent blues". She alludes to The Beatles and Paul McCartney in the song "Edit". She also used a line from Joni Mitchell's California in her song "The Devil Came to Bethlehem". Recurring themes and topics in Spektor's lyrics include love, death, religion (particularly Biblical and Jewish references), city life (particularly New York references), and certain key phrases have been known to recur in different songs by Spektor, such as references to gravediggers, the Tree of Knowledge of Good and Evil and the name "Mary Ann". Spektor's use of satire is evident in "Wasteside," which refers to The Twelve Chairs, the classic satirical novel by the Soviet authors Ilf and Petrov, and describes the town in which people are born, get their hair cut, and then are sent to the cemetery.

In Spektor's early albums, many of her tracks had a very dry vocal production, with very little reverb or delay added. However, Spektor's more recent albums, particularly Begin to Hope, have put more emphasis into song production and have relied more on traditional pop and rock instruments.^[3] Spektor says the records that most impact her are those of "bands whose music is really involved",^[20] specifically naming The Beatles, Bob Dylan, Billie Holiday, Radiohead, Tom Waits, and Frédéric Chopin as primary influences.^[20][21]

In her songs, "Eet", "Us" and "Après Moi" the titular sounds are used as the focal point throughout. (In "Dance Anthem of the 80's", the sound "eet" is also used often, on words such as "meat", "street", and "eat").

Performances[link]

Regina Spektor at her first performance in Tel Aviv, Israel on March 3, 2007

Spektor's first nationwide tour was accompanying The Strokes as the opening act on their 2003–2004 Room on Fire tour, during which she and the band performed and recorded "Modern Girls & Old Fashion Men". Kings of Leon were the second opening act on that tour, and they invited Regina to open for them on their own European tour right after The Strokes tour. In June 2005, Spektor was the opening act for the English piano rock band Keane on their North American tour, during which she performed at Radio City Music Hall on June 7, 2005.^[22] During her 2006 headlining tour in support of the Begin to Hope album, Spektor sold out a performance at Messiah College in Grantham, Pennsylvania, and two shows at Town Hall Theater in New York City on September 27 and September 28, 2006.^[23]

Spektor has appeared on The Tonight Show with Conan O'Brien (once), Late Night with Conan O'Brien (three times), The Tonight Show with Jay Leno (twice), Jimmy Kimmel Live (twice), Last Call with Carson Daly (five times), Late Show with David Letterman (twice), Late Night with Jimmy Fallon (twice), CBS News Sunday Morning, Good Morning America (twice), Australia's Rove Live, and The Late Late Show with Craig Ferguson (twice).^[24] On October 10, 2009 she performed on Saturday Night Live.

Since January 2005, Spektor has performed on a bright red Baldwin baby grand piano.^[25] At the present time she uses exclusively Steinway & Sons pianos. She plays a seafoam Epiphone Wildkat archtop hollow-body electric guitar.^[26]

Although she generally only performs original material, Spektor occasionally performs covers. Most famous of these covers were her performances of songs by Leonard Cohen and Madonna, for the 2nd Annual Jewish Music & Heritage Festival at the 92nd Street Y in New York City.^[4] In 2006 and 2007, Spektor embarked on a headlining tour of the U.S. and Europe, selling out numerous clubs and theaters. She covered John Lennon's "Real Love" at the performance arts center of her alma mater, State University of New York at Purchase, on March 28, 2007, at a benefit concert for the Conservatory of Music.^[27] In 2007, Spektor recorded "Real Love" for the Instant Karma: The Amnesty International Campaign to Save Darfur CD, which was released in June of that year. She recorded a version of the song for Triple J's Like a Version radio segment which was shown on jTV.

Regina Spektor performing in Brighton on October 26, 2006.

On March 8, 2007, Spektor appeared on the British ITV network's Loose Women, promoting and performing "Fidelity" live, and on April 20, 2007, she performed on the Late Show with David Letterman. On Saturday, April 28, 2007, she appeared at the Coachella Valley Music and Arts Festival. On Friday, May 18, 2007, she appeared on BBC1's Friday Night with Jonathan Ross. On June 16, 2007, she performed at the Bonnaroo Music Festival and later performed at the 2007 Lollapalooza on August 4, 2007 and Virgin Festival on August 5, 2007 in Baltimore, Maryland. On September 16, 2007, she performed at the Austin City Limits Music Festival and recorded a set for the Austin City Limits TV show the following day. She performed acoustic at the Bridge School Benefit at Shoreline Amphitheatre on October 27 and October 28, 2007.

On November 14, 2007, at her concert at Ryman Auditorium, in Nashville, it was announced that Spektor collapsed during the sound check and was taken to a local emergency room. According to the statement given to the audience, Spektor was fine, but doctors said that she could not perform that night. It was later reported that the cause of the collapse was an inner ear infection which caused intense vertigo. The show was initially rescheduled for December 6, 2007,^[28] but the date was once again rescheduled, and the concert finally occurred on February 29, 2008.^[29] After her initial collapse in Nashville, she was able to perform in concerts at Mountain Stage on November 18, 2007,^{[30][citation needed]} and at Duke University on November 19, 2007.^[31]

In conjunction with the release of her 2009 album Far, Spektor was headlining at Serpentine Sessions, a series of concerts London's Hyde Park on June 29, 2009. Other European performances in 2009 include Glastonbury Festival, Hultsfred Festival, Oxegen 2009, T in the Park, Paradiso (Amsterdam), Latitude Festival, and Rock Werchter. Spektor has invited Brooklyn-based rock band Jupiter One to open concerts on her 2009 North American tour. As a part of that tour, on October 14, 2009 Spektor headlined a concert at the Radio City Music Hall in NYC.

On July 7, 2010, Regina performed at the Montreux Jazz Festival in Montreux, Switzerland.^[32] Her cellist, Dan Cho, drowned the day before while swimming in Lake Geneva near the Chillon Castle.^[33][34] She was described as distraught, shaken, and in tears and took several breaks to regain her composure.^[35]

Media coverage[link]

Spektor performing at the Hammerstein Ballroom on October 16, 2007

Regina Spektor performing in the West London Synagogue, February 2007.

Since 2005, Spektor's music has been used in various television programs and commercials. In late 2005 "Us" (from Soviet Kitsch) was used in a commercial as part of the What Do You Want To Watch? series for the United Kingdom's British Sky Broadcasting. The advert features a clip from a documentary on skateboarder Danny Way. In the summer of 2006, a clip from "Us" was used for the teaser website for Microsoft's Zune project at ComingZune.com, as well as for a promotional campaign for MtvU. The same track is used by Dutch telecom company KPN in a commercial. "Somedays" was used in a 2005 episode of CSI: NY and "Samson" was used in a 2006 episode of the same series. "On the Radio" was used in an episode of ABC's Grey's Anatomy. "Field Below" was used in a 2006 episode titled "The Last Word" of CBS's Criminal Minds. "Fidelity" has also been used in an episode of Grey's Anatomy titled "Six Days, Part 2", Veronica Mars titled "Wichita Linebacker", Brothers & Sisters titled "Sexual Politics", during the end credits of Love and Other Drugs, and in the Brazilian telenovela A Favorita. "Better" is currently being used in a commercial for XM Satellite Radio, an episode of "How I Met Your Mother", and the popular film My Sister's Keeper. Her song "Music Box" is currently being used in a commercial for JC Penney. Spektor also sang the title song "Little Boxes" of Showtime's television series Weeds in the episode "Mile Deep and a Foot Wide" (2006) and her "Ghost of Corporate Future" was used both at the beginning and end of the episode.^[36] On January 21, 2007, she was featured on CBS News Sunday Morning.^[11]

Spektor received increased attention in 2006 when her video for "Fidelity" was viewed over 200,000 times in two days on YouTube. On Sirius Radio's Left of Center channel, her single "Fidelity" was voted by listeners as the #1 song of 2006. Towards the end of 2006, VH1 showcased her as part of their "You Oughta Know: Artists on the Rise" featurettes: they played clips from the "Fidelity" music video and showed parts of an interview with Spektor during commercial breaks on the channel.^[37] Spektor's video for "Fidelity" reached #3 on VH1's Top 20 Countdown.^{[citation needed]}

Peter Gabriel recorded a version of "Après Moi" on his 2010 release Scratch My Back.

In Australia, Spektor's music has rapidly gained popularity in mainstream culture primarily due to Begin to Hope being played on the nation-wide radio station Triple J, where it eventually became a feature album. Prior to Begin to Hope, Spektor had only a small following in Australia in comparison to the US and Europe.

Spektor reached #33 on Blender magazine's top 100 of 2006 and was also listed as one of the "Hottest Women of...Rock!".^[38] "Fidelity" was also used in a 2007 television commercial in New Zealand advertising Yahoo!Xtra, a new partnership between Yahoo! and Telecom's Xtra ISP. Also in 2007, the mobile phone company Vodafone used her lyric, "Come into my world..." from the track, "Hotel Song" on Begin to Hope, in an extensive TV advertising campaign in the UK and Ireland.

On October 1, 2007, Spektor's new video for "Better" was released on VH1 and YouTube, where it was viewed more than 100,000 times within the first 24 hours. "Fidelity" was used in the trailer for the film 27 Dresses, released on October 3, 2007.^[39]

Her song "The Call" appeared prominently in The Chronicles of Narnia: Prince Caspian,^[40] as part of the film's finale sequence. Spektor's song "Better" was used in the movie My Sister's Keeper, loosely based on the novel of the same name by Jodi Picoult. A section of "That Time" was featured in the film In Bruges. Additionally, "Us" and "Hero" are both featured on the soundtrack for the film (500) Days of Summer. Spin magazine profiled Spektor in their July 2009 issue, where she discussed her just-released album Far. The story was released in their digital edition that month, as well.^[41] In August 2009, the song "Two Birds" was used in the 2009 Fall Campaign of the Polish TV station TVN. Also Regina's song "Eet" debuted on the show 90210 in April 2010.

On September 16, 2009, it was announced that Spektor would write the music for the musical Beauty, a modern adaptation of the fairy tale Sleeping Beauty, which is set to open during the 2011–12 Broadway season.^[42]

In May 2010, Spektor performed for President Obama and his wife Michelle along with hundreds of other guests at the White House reception in honor of Jewish Heritage Month. She sang "Us" and "The Sword & the Pen", receiving a standing ovation begun by Michelle Obama.

The song "Human of the Year" featured prominently in the trailer and first episode of the 2011 HBO series Enlightened.

The song "All the Rowboats" was featured on The CW's Ringer in March 2012.

The Song "Hotel Song" was featured in the opening of the movie Friends with Kids.

Philanthropy[link]

In 2007, she covered John Lennon's "Real Love" for Instant Karma: The Amnesty International Campaign to Save Darfur. The following year, she participated in Songs for Tibet, an initiative to support the human rights situation in Tibet and the 14th Dalai Lama. The album was issued on August 5, 2008, via iTunes and on August 19 in music stores around the world.^[43] On January 22, 2009, Spektor performed at the third annual Roe On The Rocks gig at the Bowery Ballroom to raise money for Planned Parenthood New York City.^[44] Also, continuing with her support for Tibet, Regina Spektor played for Tibet House's annual concert at Carnegie Hall on February 26, 2010. Less than one month later, on March 23, 2010, Spektor gave a concert at the Fillmore at Irving Plaza in New York City to raise funds for the work of Doctors Without Borders in Haiti. Also, on April 27, she released a cover of Radiohead's song "No Surprises" with all proceeds going to Doctors Without Borders to help the earthquake victims in Haiti and Chile.

Discography[link]

Albums[link]

• 2001: 11:11
• 2002: Songs
• 2004: Soviet Kitsch
• 2006: Begin to Hope
• 2009: Far
• 2012: What We Saw from the Cheap Seats

Singles[link]

Awards[link]

• Begin to Hope – Shortlist Music Prize (nominated)
• Studio8's Female Voice of August 2009 (won)

References[link]