Names | |||
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Preferred IUPAC name Thiirane | |||
Systematic IUPAC name Thiacyclopropane | |||
Other names | |||
Identifiers | |||
3D model (JSmol) | |||
102379 | |||
ChEBI | |||
ChemSpider | |||
ECHA InfoCard | 100.006.359 | ||
EC Number |
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1278 | |||
KEGG | |||
MeSH | ethylene+sulfide | ||
PubChem CID | |||
RTECS number |
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UNII | |||
UN number | 1992 | ||
CompTox Dashboard (EPA) | |||
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Properties | |||
C2H4S | |||
Molar mass | 60.11 g·mol−1 | ||
Appearance | Pale, yellow liquid | ||
Density | 1.01 g cm−3 | ||
Melting point | −109 °C (−164 °F; 164 K) | ||
Boiling point | 56 °C; 133 °F; 329 K | ||
Vapor pressure | 28.6 kPa (at 20 °C) | ||
Thermochemistry | |||
Std enthalpy of formation (ΔfH⦵298) | 51-53 kJ mol−1 | ||
Std enthalpy of combustion (ΔcH⦵298) | -2.0126 MJ mol−1 | ||
Hazards | |||
GHS labelling: | |||
Danger | |||
H225, H301, H318, H331 | |||
P210, P261, P280, P301+P310, P305+P351+P338, P311 | |||
NFPA 704 (fire diamond) | |||
Flash point | 10 °C (50 °F; 283 K) | ||
Related compounds | |||
Related heterocycles | Ethylene oxide Aziridine Borirane | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Thiirane, more commonly known as ethylene sulfide, is the cyclic chemical compound with the formula C2H4S. [2] It is the smallest sulfur-containing heterocycle and the simplest episulfide. Like many organosulfur compounds, this species has a highly unpleasant odour. Thiirane is also used to describe any derivative of the parent ethylene sulfide.
According to electron diffraction, the C-C and C-S distances in ethylene sulfide are respectively 1.473 and 1.811 Å. The C-C-S and C-S-C angles are respectively 66.0 and 48.0°. [3]
It can be prepared by the reaction of ethylene carbonate and KSCN. [4] For this purpose the KSCN is first melted under vacuum to remove water.
Ethylenesulfide adds to amines to afford 2-mercaptoethylamines, [5] which are good chelating ligands.
This process is often called mercaptoethylation. [6]
Oxidation of thiirane with periodate gives ethylene episulfoxide.
Sulfur (also spelled sulphur in British English) is a chemical element; it has symbol S and atomic number 16. It is abundant, multivalent and nonmetallic. Under normal conditions, sulfur atoms form cyclic octatomic molecules with the chemical formula S8. Elemental sulfur is a bright yellow, crystalline solid at room temperature.
In organic chemistry, a thiol, or thiol derivative, is any organosulfur compound of the form R−SH, where R represents an alkyl or other organic substituent. The −SH functional group itself is referred to as either a thiol group or a sulfhydryl group, or a sulfanyl group. Thiols are the sulfur analogue of alcohols, and the word is a blend of "thio-" with "alcohol".
In organic chemistry, a sulfide or thioether is an organosulfur functional group with the connectivity R−S−R' as shown on right. Like many other sulfur-containing compounds, volatile sulfides have foul odors. A sulfide is similar to an ether except that it contains a sulfur atom in place of the oxygen. The grouping of oxygen and sulfur in the periodic table suggests that the chemical properties of ethers and sulfides are somewhat similar, though the extent to which this is true in practice varies depending on the application.
In organic chemistry, thioesters are organosulfur compounds with the molecular structure R−C(=O)−S−R’. They are analogous to carboxylate esters with the sulfur in the thioester replacing oxygen in the carboxylate ester, as implied by the thio- prefix. They are the product of esterification of a carboxylic acid with a thiol. In biochemistry, the best-known thioesters are derivatives of coenzyme A, e.g., acetyl-CoA. The R and R' represent organyl groups, or H in the case of R.
Sulfur monoxide is an inorganic compound with formula SO. It is only found as a dilute gas phase. When concentrated or condensed, it converts to S2O2 (disulfur dioxide). It has been detected in space but is rarely encountered intact otherwise.
In organic chemistry, sulfonic acid refers to a member of the class of organosulfur compounds with the general formula R−S(=O)2−OH, where R is an organic alkyl or aryl group and the S(=O)2(OH) group a sulfonyl hydroxide. As a substituent, it is known as a sulfo group. A sulfonic acid can be thought of as sulfuric acid with one hydroxyl group replaced by an organic substituent. The parent compound is the parent sulfonic acid, HS(=O)2(OH), a tautomer of sulfurous acid, S(=O)(OH)2. Salts or esters of sulfonic acids are called sulfonates.
Organosulfur chemistry is the study of the properties and synthesis of organosulfur compounds, which are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur derivatives, e.g., saccharin. Nature is abound with organosulfur compounds—sulfur is vital for life. Of the 20 common amino acids, two are organosulfur compounds, and the antibiotics penicillin and sulfa drugs both contain sulfur. While sulfur-containing antibiotics save many lives, sulfur mustard is a deadly chemical warfare agent. Fossil fuels, coal, petroleum, and natural gas, which are derived from ancient organisms, necessarily contain organosulfur compounds, the removal of which is a major focus of oil refineries.
In organic chemistry, a sulfoxide, also called a sulphoxide, is an organosulfur compound containing a sulfinyl functional group attached to two carbon atoms. It is a polar functional group. Sulfoxides are oxidized derivatives of sulfides. Examples of important sulfoxides are alliin, a precursor to the compound that gives freshly crushed garlic its aroma, and dimethyl sulfoxide (DMSO), a common solvent.
In organic chemistry, a sulfonium ion, also known as sulphonium ion or sulfanium ion, is a positively-charged ion featuring three organic substituents attached to sulfur. These organosulfur compounds have the formula [SR3]+. Together with a negatively-charged counterion, they give sulfonium salts. They are typically colorless solids that are soluble in organic solvent.
In organic chemistry, thioketones are organosulfur compounds related to conventional ketones in which the oxygen has been replaced by a sulfur. Instead of a structure of R2C=O, thioketones have the structure R2C=S, which is reflected by the prefix "thio-" in the name of the functional group. Thus the simplest thioketone is thioacetone, the sulfur analog of acetone. Unhindered alkylthioketones typically tend to form polymers or rings.
Sulfur compounds are chemical compounds formed the element sulfur (S). Common oxidation states of sulfur range from −2 to +6. Sulfur forms stable compounds with all elements except the noble gases.
Thiophenol is an organosulfur compound with the formula C6H5SH, sometimes abbreviated as PhSH. This foul-smelling colorless liquid is the simplest aromatic thiol. The chemical structures of thiophenol and its derivatives are analogous to phenols, where the oxygen atom in the hydroxyl group (-OH) bonded to the aromatic ring in phenol is replaced by a sulfur atom. The prefix thio- implies a sulfur-containing compound and when used before a root word name for a compound which would normally contain an oxygen atom, in the case of 'thiol' that the alcohol oxygen atom is replaced by a sulfur atom.
Sulfur dichloride is the chemical compound with the formula SCl2. This cherry-red liquid is the simplest sulfur chloride and one of the most common, and it is used as a precursor to organosulfur compounds. It is a highly corrosive and toxic substance, and it reacts on contact with water to form chlorine-containing acids.
In organic chemistry, episulfides are a class of organic compounds that contain a saturated, heterocyclic ring consisting of two carbon atoms and one sulfur atom. It is the sulfur analogue of an epoxide or aziridine. They are also known as thiiranes, olefin sulfides, thioalkylene oxides, and thiacyclopropanes. Episulfides are less common and generally less stable than epoxides. The most common derivative is ethylene sulfide.
Disulfur dichloride is the inorganic compound of sulfur and chlorine with the formula S2Cl2. It is an amber oily liquid.
Potassium thiocyanate is the chemical compound with the molecular formula KSCN. It is an important salt of the thiocyanate anion, one of the pseudohalides. The compound has a low melting point relative to most other inorganic salts.
In organic chemistry, thioureas are members of a family of organosulfur compounds with the formula S=C(NR2)2 and structure R2N−C(=S)−NR2. The parent member of this class of compounds is thiourea. Substituted thioureas are found in several commercial chemicals.
Diethyl sulfide is an organosulfur compound with the chemical formula (CH3CH2)2S. It is a colorless, malodorous liquid. Although a common thioether, it has few applications.
Thietane is a heterocyclic compound containing a saturated four-membered ring with three carbon atoms and one sulfur atom.
In organic chemistry, thiocarboxylic acids or carbothioic acids are organosulfur compounds related to carboxylic acids by replacement of one of the oxygen atoms with a sulfur atom. Two tautomers are possible: a thione form and a thiol form. These are sometimes also referred to as "carbothioic O-acid" and "carbothioic S-acid" respectively. Of these the thiol form is most common.