Carbon diselenide

Carbon diselenide is an inorganic compound with the chemical formula CSe2. It is a yellow-orange oily liquid with pungent odor. It is an analogue of carbon disulfide (CS2). This light-sensitive compound is insoluble in water and soluble in organic solvents.

Carbon diselenide
Carbon diselenide
Carbon-diselenide-3D-balls
Carbon-diselenide-3D-vdW
Names
Other names
Carbon selenide, diselenoxomethane, methanediselone
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.323
Properties
CSe2
Molar mass 169.93 g/mol
Appearance Yellow liquid
Density 2.6824 g/cm3
Melting point −43.7 °C (−46.7 °F; 229.5 K)
Boiling point 125.5 °C (257.9 °F; 398.6 K)
0.054 g/100 mL
Solubility Soluble in CS2, toluene
0 D
Thermochemistry
5032 J/mol K
263.2 J/mol K
219.2 kJ/mol
Hazards
Flash point 30 °C (86 °F; 303 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Synthesis, structure and reactions

Carbon diselenide is a linear molecule with D∞h symmetry. It is produced by reacting selenium powder with dichloromethane vapor near 550 °C.[1]

2 Se + CH2Cl2 → CSe2 + 2 HCl

It was first reported by Grimm and Metzger, who prepared it by treating hydrogen selenide with carbon tetrachloride in a hot tube.[2]

Like carbon disulfide, carbon diselenide polymerizes under high pressure. The structure of the polymer is thought to be a head-to-head structure with a backbone in the form of –[Se–C(=Se)–C(=Se)–Se]–.[3] The polymer is a semiconductor with a room-temperature conductivity of 50 S/cm.

In addition, carbon diselenide is a precursor to tetraselenafulvalenes,[4] the selenium analogue of tetrathiafulvalene, which can be further used to synthesize organic conductors and organic superconductors.

Carbon diselenide reacts with secondary amines to give dialkydiselenocarbamates:[1]

2 Et2NH + CSe2 → (Et2NH2+)(Et2NCSe2)

Safety

Carbon diselenide has high vapor pressure. It has a moderate toxicity and presents an inhalation hazard. It may be dangerous due to its easy membrane transport. It decomposes slowly in storage (about 1% per month at –30 °C). When obtained commercially, its cost is high.[5]

Pure distilled carbon diselenide has an odor very similar to that of carbon disulfide, but mixed with air, it creates extremely offensive odors (corresponding to new, highly toxic reaction products).[6][7] Because of the odor, synthetic pathways have been developed to avoid its use.[8] Its smell forced an evacuation of a nearby village when it was first synthesized in 1936. [7] Because of the odor, synthetic pathways have been developed to avoid its use.[8]

References

  1. ^ a b Pan, W.-H.; Fackler, J. P. Jr.; Anderson, D. M.; Henderson, S. G. D.; Stephenson, T. A. (1982). "2. Diselenocarbamates from Carbon Diselenide". In Fackler, J. P. Jr. (ed.). Inorganic Syntheses. 21. pp. 6–11. doi:10.1002/9780470132524.ch2. ISBN 978-0-470-13252-4.
  2. ^ Grimm, H. G.; Metzger, H. (1936). "Über Darstellung und Eigenschaften des Selenkohlenstoffs". Berichte der Deutschen Chemischen Gesellschaft (A and B Series). 69 (6): 1356–1364. doi:10.1002/cber.19360690626.
  3. ^ Carraher, C. E. Jr.; Pittman, C. U. Jr. (2005). "Poly(Carbon Disulfide), Poly(Carbon Diselenide), and Polythiocyanogen". Inorganic Polymers. 21. doi:10.1002/14356007.a14_241. ISBN 3-527-30673-0.
  4. ^ Engler, E. M.; Patel, V. V. (1974). "Structure control in organic metals. Synthesis of tetraselenofulvalene and its charge transfer salt with tetracyano-p-quinodimethane". Journal of the American Chemical Society. 96 (23): 7376–7378. doi:10.1021/ja00810a042. PMID 4814748.
  5. ^ "Carbon Diselenide CSe2". Cse2.com. Retrieved 2012-04-04.
  6. ^ Wolfgang H. H. Gunther. Organic Selenium Compounds: Their Chemistry and Biology. carbon diselenide has by far the worst odor this author has experienced in his lifetime of working with selenium compounds
  7. ^ a b Lowe, Derek (2005-03-03). "Things I Won't Work With: Carbon Diselenide". In the Pipeline. Science. Retrieved 20 November 2015.
  8. ^ a b US patent 4462938, Wudl, F., "Process for producing chalcogen containing compounds", issued 1984-07-31, assigned to AT&T Bell Laboratories.
Beryllium carbide

Beryllium carbide, or Be2C, is a metal carbide. Similar to diamond, it is a very hard compound.

Carbon dioxide

Carbon dioxide (chemical formula CO2) is a colorless gas with a density about 60% higher than that of dry air. Carbon dioxide consists of a carbon atom covalently double bonded to two oxygen atoms. It occurs naturally in Earth's atmosphere as a trace gas. The current concentration is about 0.04% (410 ppm) by volume, having risen from pre-industrial levels of 280 ppm. Natural sources include volcanoes, hot springs and geysers, and it is freed from carbonate rocks by dissolution in water and acids. Because carbon dioxide is soluble in water, it occurs naturally in groundwater, rivers and lakes, ice caps, glaciers and seawater. It is present in deposits of petroleum and natural gas. Carbon dioxide is odorless at normally encountered concentrations, but at high concentrations, it has a sharp and acidic odor.As the source of available carbon in the carbon cycle, atmospheric carbon dioxide is the primary carbon source for life on Earth and its concentration in Earth's pre-industrial atmosphere since late in the Precambrian has been regulated by photosynthetic organisms and geological phenomena. Plants, algae and cyanobacteria use light energy to photosynthesize carbohydrate from carbon dioxide and water, with oxygen produced as a waste product.CO2 is produced by all aerobic organisms when they metabolize carbohydrates and lipids to produce energy by respiration. It is returned to water via the gills of fish and to the air via the lungs of air-breathing land animals, including humans. Carbon dioxide is produced during the processes of decay of organic materials and the fermentation of sugars in bread, beer and wine making. It is produced by combustion of wood and other organic materials and fossil fuels such as coal, peat, petroleum and natural gas. It is an unwanted byproduct in many large scale oxidation processes, for example, in the production of acrylic acid (over 5 million tons/year).It is a versatile industrial material, used, for example, as an inert gas in welding and fire extinguishers, as a pressurizing gas in air guns and oil recovery, as a chemical feedstock and as a supercritical fluid solvent in decaffeination of coffee and supercritical drying. It is added to drinking water and carbonated beverages including beer and sparkling wine to add effervescence. The frozen solid form of CO2, known as dry ice is used as a refrigerant and as an abrasive in dry-ice blasting.

Carbon dioxide is the most significant long-lived greenhouse gas in Earth's atmosphere. Since the Industrial Revolution anthropogenic emissions – primarily from use of fossil fuels and deforestation – have rapidly increased its concentration in the atmosphere, leading to global warming. Carbon dioxide also causes ocean acidification because it dissolves in water to form carbonic acid.

Carbon disulfide

Carbon disulfide is a colorless volatile liquid with the formula CS2. The compound is used frequently as a building block in organic chemistry as well as an industrial and chemical non-polar solvent. It has an "ether-like" odor, but commercial samples are typically contaminated with foul-smelling impurities.

Diselenide

Diselenide may refer to:

Diselane, H-Se-Se-H

Carbon diselenide, CSe2, a yellow-orange oily liquid with pungent odor

Any organic chemical compound with a selenium-selenium bond, R-Se-Se-R

Diphenyl diselenide, (C6H5)–Se–Se–(C6H5)

Metal dichalcogenides

Manganese diselenide (MnSe2)

Molybdenum diselenide (MoSe2)

Tungsten diselenide (WSe2)

Titanium diselenide (TiSe2)

Heterocumulene

A heterocumulene is a molecule or ion containing a chain of at least three double bonds between consecutive atoms, in which one or more atoms in the doubly bonded chain is a heteroatom. Such species are analogous to a cumulene in which the chain of doubly bonded atoms contains only carbon, except that at least one carbon is replaced by a heteroatom. Some authors relax the definition to include species with chains of only two double bonds between consecutive atoms, also known as heteroallenes.

Because of the double bond rule, heterocumulenes are rarely isolated. Instead they tend to polymerize. Many are however common in the interstellar medium, where they exist as a dilute gas. Most of the longer ones are very unstable and reactive, and thus have a transient existence, or can only survive when dilute or in an inert matrix. Molecular clouds in space are very dilute and allow heterocumulenes to exist long enough to be detected. Some simple heterocumulenes are common chemicals or ions. These include carbon dioxide, carbon disulfide, carbon diselenide, cyanate, thiocyanate. Some definitions of heterocumulenes include compounds that contain concatenated double bonds with more than one element, but may have other parts to them. This class includes ketene, sulfur diimide, sulfine and dicyclohexylcarbodiimide. Some heterocumulenes can act as ligands with various metals.

List of compounds with carbon number 1

This is a partial list of molecules that contain 1 carbon atom.

Compounds
Carbon ions
Oxides and related

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