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Encyclopedia > Organosulfur compounds

Organosulfur compounds are organic compounds that contain sulfur. They are often associated with foul odours, but ironically many of the sweetest compounds known are organosulfur derivatives. Nature abounds with organosulfur compounds - sulfur is essential for life. Two of the 20 common amino acids are organosulfur compounds. 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 on oil refineries. Benzene An organic compound is any member of a large class of chemical compounds whose molecules contain carbon, with the exception of carbides, carbonates, carbon oxides and elementary carbon. ... General Name, Symbol, Number sulfur, S, 16 Chemical series nonmetals Group, Period, Block 16, 3, p Appearance lemon yellow Atomic mass 32. ... Coal Coal is a fossil fuel extracted from the ground by underground mining or open-pit mining (surface mining). ... Pumpjack pumping an oil well near Sarnia, Ontario Petroleum (from Greek petra – rock and elaion – oil or Latin oleum – oil ) or crude oil is a black, dark brown or greenish liquid found in porous rock formations in the earth. ... Many stoves use natural gas. ... View of the Shell/Valero Martinez oil refinery An oil refinery is an industrial process plant where crude oil is processed and refined into useful petroleum products. ...


Sulfur shares the chalcogen group with oxygen, and it is expected that organosulfur compounds have similarities with carbon-oxygen compounds, which is true to some extent. The chalcogens (with the ch pronounced with a hard c as in chemistry) are the name for the periodic table group 16 (old-style: VIB or VIA) in the periodic table. ...


A classical chemical test for the detection of sulfur compounds is the Carius halogen method. In chemistry, a chemical test is qualitative or semi-quantitative procedure designed to prove the existence of a chemical compound or chemical group with the aid of a specific reagent. ... The Carius halogen method in analytical chemistry is a method for the quantitative determination of halogens in chemical substances [1]. In this technique a chemical substance is oxidized with fuming nitric acid under pressure (in a sealed glass tube) in the presence of silver nitrate at a maximum operating temperature...

Contents


Classes of organosulfur compounds

Organosulfur compounds can be classified according to the sulfur-containing functional groups, which are listing in decreasing order of their occurrence.


Thioethers

Thioethers are characterized by C-S-Cbonds. The C-S bond is both longer, because S is larger, and weaker than C-C bonds. Selected bond lengths in sulfur compounds are 183 pm for the S-C single bond in methanethiol and 173 pm in thiophene. The C-S bond dissociation energy for thiomethane is 89 Kcal/mol compared to methane's 100 Kcal/mol and when hydrogen is replaced by a methyl group the energy decreases to 73 Kcal/mol [1]. A chemical bond is the physical phenomenon of chemical substances being held together by attraction of atoms to each other through sharing, as well as exchanging, of electrons or electrostatic forces. ... Bond length or bond distance in molecular geometry is the distance between two bonded atoms in a molecule. ... Picometre (American spelling: picometer) is an SI measure of length that is equal to 10−12 of a metre. ... Methanethiol (also known as methyl mercaptan) is a colorless gas with a smell like rotten cabbage. ... Thiophene is an aromatic heterocyclic compound consisting of four carbon atoms and one sulfur atom in a five-membered ring. ... In chemistry, bond dissociation energy, D0, is one measure of the bond strength in a chemical bond. ...


The single carbon to oxygen bond is shorter than that of the C-C bond. The bond dissociation energies for dimethylsulfide and dimethyl ether are respectively 73 and 77 Kcal/mol. In chemistry, bond dissociation energy, D0, is one measure of the bond strength in a chemical bond. ... Dimethylsulfide (DMS; CH3SCH3) is a volatile sulfur gas, and the most abundant single biological sulfur compound emmitted to the atmosphere. ... Dimethyl ether, also known as methoxymethane, oxybismethane, methyl ether, wood ether, and DME, is a colorless gaseous ether with an ethereal odor. ...


Thioethers are typically prepared by alkylation of thiols. They can also be prepared via the Pummerer rearrangement. The Pummerer rearrangement is a chemical reaction whereby an alkyl sulfoxide rearranges to an α-acyloxythioether in the presence of acetic anhydride. ...



Thioacetals, which are useful in umpolung of carbonyl groups, are a special class of thioethers. An acetyl group that contains a sulfur atom (see thiol) This page is a candidate to be copied to Wiktionary. ... Umpolung or polarity inversion in organic chemistry is the chemical modification of a functional group with the aim the reversal of polarity of that group. ...


Thiophenes represent a special class of thioethers that are aromatic. The resonance stabilization of thiophene is 29 Kcal/mol compared to 20 kcal/mole for the oxygen analogue furan. The reason for this difference is the higher electronegativity for oxygen drawing away electrons to itself at the expense of the aromatic ring current. Yet as an aromatic substituent the thio group is less effective as an activating group than the alkoxy group. In chemistry, an aromatic molecule is one in which electrons are free to cycle around circular arrangements of atoms, which are alternately singly and doubly bonded to one another. ... Resonance in chemistry is a tool used (predominately in organic chemistry) to represent certain types of molecular structures. ... Thiophene is an aromatic heterocyclic compound consisting of four carbon atoms and one sulfur atom in a five-membered ring. ... Furan, also known as furane and furfuran, is an aromatic heterocyclic organic compound, produced when wood, especially pine-wood, is distilled. ... Electronegativity is a measure of the ability of an atom or molecule to attract electrons in the context of a chemical bond. ... In organic chemistry, a substituent is an atom or group of atoms substituted in place of a hydrogen atom on the parent chain of a hydrocarbon. ... In organic chemistry, a functional group is called an activating group if a benzene molecule to which it is attached more readily participates in electrophilic substitution reactions. ...


Thiols

Thiol group contain the functionality R-SH. Thiols are structurally similar to the alcohol group, but these functionalities are very different in their chemical properties. Thiols are correspondingly more nucleophilic, more acidic, and more readily oxidized. This acidity can differ by 5 pKa units [2]. In organic chemistry, a thiol is a compound that contains the functional group composed of a sulfur atom and a hydrogen atom (-SH). ... In chemistry, an alcohol is any organic compound in which a hydroxyl group (-OH) is bound to a carbon atom of an alkyl or substituted alkyl group. ... In chemistry, a nucleophile (literally nucleus lover) is a reagent which is attracted to centres of positive charge. ... In chemistry and biochemistry, acid dissociation constant, the acidity constant, or the acid-ionization constant () is a specific type of equilibrium constant that indicates the extent of dissociation of hydrogen ions from an acid. ...


The diffence in electronegativity between sulfur (2.58) and hydrogen (2.20) is small and therefore hydrogen bonding in thiols is not prominent. Aliphatic thiols form monolayers on gold, which are topical in nanotechnology. Electronegativity is a measure of the ability of an atom or molecule to attract electrons in the context of a chemical bond. ... In chemistry, a hydrogen bond is a type of attractive intermolecular force that exists between two partial electric charges of opposite polarity. ... A monolayer is a single, closely packed layer of atoms or molecules [1]. A Langmuir monolayer is a one-molecule thick insoluble layer of an organic material spread onto an aqueous subphase. ... General Name, Symbol, Number gold, Au, 79 Chemical series transition metals Group, Period, Block 11, 6, d Appearance metallic yellow Atomic mass 196. ... Molecular gears from a NASA computer simulation. ...


Sulfoxides, sulfones

Sulfoxide have the general structure RS(=O)R' also represented RS+(O-)R'. They are obtained by oxidation of thioethers. A well-known sulfoxide is dmso. Sulfoxides can be oxidized even further to Sulfones (RS(=O)2R). A sulfoxide is a chemical compound containing a sulfinyl functional group with a sulfur oxygen double bond attached to two carbon atoms. ... A thioether (also known as a sulfide) is a functional group in organic chemistry that has the structure R-S-R, where R is any organic group. ... Dimethyl sulfoxide The United States DoDs Defense Modeling and Simulation Office This is a disambiguation page — a navigational aid which lists other pages that might otherwise share the same title. ... A sulfone is a chemical compound containing a sulfonyl functional group attached to two carbon atoms. ...


Double bonds between C and S

Double bonds of carbon and sulfur are relatively uncommon, because such species often tend to oligomerize or polymerize. A famous exception to this rule include carbon disulfide, carbonylsulfide, and thiophosgene. Also thioamides are often highly stable. Covalent bonding is a form of chemical bonding characterized by the sharing of one or more pairs of electrons between atoms, in order to produce a mutual attraction, which holds the resultant molecule together. ... Carbon disulfide (CS2) is a colorless liquid with a pleasant odor that is like the smell of chloroform. ... Thiophosgene is a yellow liquid with the formula CSCl2. ...


Thioketone have the general structure RC(=S)R'. These species are quite rare, in contrast to their oxygen analogues. Thioaldehydes are rarer still, reflecting their lack of steric protection. Thioketones are organic compounds which are like ketones but where the carbonyl oxygen has been replaced with a sulfur atom. ...


Thioamides, with the formula are more common. They are typically prepared by the reaction of amides with Lawesson's reagent. Thioamides are a group of drugs used to control thyrotoxicosis. ... Lawessons reagent or LR is a chemical compound used in organic synthesis as a thiation agent. ...


Double bonds of carbon and sulfur exist as Sulfonium ylides for instance in the Johnson-Corey-Chaykovsky reaction. An ylide is a neutral molecule with positive and negative charges on adjacent atoms. ... The Johnson-Corey-Chaykovsky reaction is a chemical reaction in which a carbonyl is converted to an epoxide by the action of a sulfonium ylide. ...


Sulfonic acids, esters, amides

Sulfonic acids have functionality RS(=O)2OH. They are strong acids that are typically soluble in organic solvents. Sulfonic acids like Trifluoromethanesulfonic acid is a frequently used reagent in organic chemistry. Sulfa drugs are sulfonamides derived from aromatic sulfonation. It has been suggested that Sulfonic acid/Temp be merged into this article or section. ... Trifluoromethanesulfonic acid, also known as triflic acid or TfOH, is a sulfonic acid with the chemical formula CF3SO3H . ... Organic chemistry is a specific discipline within the subject of chemistry. ... Sulfa drugs are synthetic antimicrobial agents that contain the sulfonamide group. ... In chemistry, the sulfonamide functional group is -S(=O)2-NH2, a sulfone group connected to an amine group. ... Aromatic sulfonation is an organic reaction in which a hydrogen atom on an arene is replaced by a sulfonic acid functional group in an electrophilic aromatic substitution. ...


Sulfuranes and persulfuranes

Sulfuranes are relatively specialized functional group that are tetravalent, hypervalent sulfur compounds, with the formula SR4 [3] and likewise persulfuranes are hexavalent SR6. All-carbon persulfuranes have been known for the heavier representatives of the chalcogen group, for instance the compound hexamethylpertellurane (Te(Me)6) was discovered in 1990 [4] by reaction of tetramethyltellurium with xenon difluoride to Te(Me)2)F2 followed by reaction with diethyl zinc. The sulfur analogue hexamethylpersulfurane SMe6 has been predicted to be stable [5] but has not been synthesized yet. In chemistry, a tetravalent atom in a molecule has 4 electrons available for chemical bonding in its outer valence shell. ... A hypervalent molecule is a molecule that contains one or more typical elements (group 1, 2, 13-18) formally bearing more than eight electrons in their valence shells. ... Valence, also known as valency or valency number, is a measure of the number of chemical bonds formed by the atoms of a given element. ... The chalcogens (with the ch pronounced with a hard c as in chemistry) are the name for the periodic table group 16 (old-style: VIB or VIA) in the periodic table. ... Xenon difluoride is a very powerful fluorinating agent, but it is one of the most stable xenon compounds. ... Diethyl zinc or DEZ is a synethetic organometallic compound. ...


The first ever all-carbon persulfurane actually synthesized in a laboratory has two methyl and two biphenyl ligands [6]: In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... Biphenyl (or Diphenyl or 1,1-Biphenyl or lemonene) is a solid compound that forms colourless to yellowish crystals. ... In chemistry, a ligand is an atom, ion, or molecule (see also: functional group) that generally donates one or more of its electrons through a coordinate covalent bond to, or shares its electrons through a covalent bond with, one or more central atoms or ions (these ligands act as a...

It is prepared from the corresponding sulfurane 1 with xenon difluoride / boron trifluoride in acetonitrile to the sulfuranyl dication 2 followed by reaction with butyllithium in tetrahydrofuran to (a stable) persulfurane 3 as the cis isomer. X-ray diffraction shows C-S bond lengths ranging between 189 and 193 pm (longer than the standard bond length) with the central sulfur atom in a distorted octahedral molecular geometry. Image File history File links Download high-resolution version (1056x420, 11 KB) Summary All Carbon Persulfurane Licensing I, the creator of this work, hereby grant the permission to copy, distribute and/or modify this document under the terms of the GNU Free Documentation License, Version 1. ... Xenon difluoride is a very powerful fluorinating agent, but it is one of the most stable xenon compounds. ... Boron trifluoride (BF3, trifluoroborane) is a pungent colourless toxic gas. ... Acetonitrile is an organic molecule, often used as a solvent, with the chemical formula of CH3CN. Also known as methyl cyanide, it is the simplest of the organic nitriles. ... An organolithium reagent is a carbon nucleophile similar to a Grignard reagent. ... Tetrahydrofuran, also known as THF, hydrofuran, oxolane, oxacyclopentane, or furanidine, is a heterocyclic organic compound. ... In chemistry, geometric isomerism is a form of stereoisomerism and describes the orientation of functional groups at the ends of a bond around which no rotation is possible. ... X-ray crystallography is a technique in crystallography in which the pattern produced by the diffraction of x-rays through the closely spaced lattice of atoms in a crystal is recorded and then analyzed to reveal the nature of that lattice. ... Bond length or bond distance in molecular geometry is the distance between two bonded atoms in a molecule. ... A generic octahedral molecule. ...


In silico experiments suggest that these bonds are very polar with the negative charges residing on carbon. in silico is an expression used to mean performed on computer or via computer simulation. ...


Naturally occuring organosulfur compounds

Not all organosulfur compounds are foul-smelling pollutants. Compounds like allicin and ajoene are responsible for the odor of garlic, and lenthionine contributes to the flavor of shiitake mushrooms. Many of these natural products also have important medicinal properties such as preventing platelet aggregation or fighting cancer. Allicin is a powerful antibiotic and anti-fungal compound obtained from garlic. ... Ajoene (pronounced ah-khoe-ene) is a chemical compound available from garlic (Allium sativum). ... Binomial name Allium sativum L. Percentages are relative to US RDI values for adults. ... Lenthionine (1,2,3,5,6-pentathiacycloheptane) is a cyclic organosulfur compound found in shiitake mushrooms and partly responsible for their flavor. ... Shiitake mushroom lentinus edodes (=lentinula edodes) Shiitake mushrooms (椎茸) are an edible mushroom typically cultivated on the shii tree (Pasania cuspidata--a relative of the oak). ... A 250 ml bag of newly collected platelets. ...


Organosulfur compounds in pollution

Most organic suflur compounds in the environment are naturally occuring, as a consequence of the fact that sulfur is essential for life and two amino acids contain this element.


Some organosulfur compounds in the environment, are generated as minor by-products of industrial processes such as the manufacture of plastics and tires.


Selected smell-producing processes are organosulfur compounds produced by the coking of coal designed to drive out sulfurus compounds and other volatile impurities in order to produce 'clean carbon' (coke), which is primarily used for steel production. Coke is a solid carbonaceous residue derived from low-ash, low-sulfur bituminous coal. ...


Organosulfur compounds in fossil fuels

Odours occur as well in chemical processing of coal or crude oil into precursor chemicals (feedstocks) for downstream industrial uses (e.g. plastics or pharmaceutical production) and the ubiquitous needs of petroleum distillation for (gasolines, diesel, and other grades of fuel oils production. A chemical substance is any material substance used in or obtained by a process in chemistry: A chemical compound is a substance consisting of two or more chemical elements that are chemically combined in fixed proportions. ... Coal Coal is a fossil fuel extracted from the ground by underground mining or open-pit mining (surface mining). ... Pumpjack pumping an oil well near Sarnia, Ontario Petroleum (from Greek petra – rock and elaion – oil or Latin oleum – oil ) or crude oil is a thick, dark brown or greenish liquid. ... A feedstock is a petrochemical used as a raw material to be fed into a machine or processing plant. ... The term plastics covers a range of synthetic or semi-synthetic organic condensation or polymerization products that can be molded or extruded into objects or films or fibers. ... Gasoline, also called petrol, is a petroleum-derived liquid mixture consisting primarily of hydrocarbons and enhanced with benzenes to increase octane ratings, used as fuel in internal combustion engines. ... Diesel fuel is a specific distillate fraction of fuel oil that is used in a diesel engine invented by German engineer Rudolf Diesel, and perfected by Charles F. Kettering. ... Fuel oil is a fraction obtained from petroleum distillation, either as a distillate or a residue. ...


Organosulfur compounds might be understood as smelly contaminants that need to be removed from natural gas before commercial uses, from exhaust stacks and exhaust vents before discharge. In this latter context, organosulfur compounds may be said to account for the pollutants in sulfurous acid rain, or equivalently, said to be pollutants within most common fossil fuels, especially coal. The effects of acid rain in the Jizera Mountains of the Czech Republic Acid rain (or more accurately acid precipitation)[1] occurs when sulfur dioxide and nitrogen oxides are emitted into the atmosphere, undergo chemical transformations and are absorbed by water droplets in clouds. ... Coal Coal is a fossil fuel extracted from the ground by underground mining or open-pit mining (surface mining). ...


See also

A period 3 element is one of the chemical elements in the third row (or period) of the periodic table of the elements. ... Organosilicon compounds are chemical compounds containing carbon silicon bonds. ... Organophosphorus compounds are chemical compounds containing carbon phosphorus bonds. ... The chalcogens are the name for the periodic table group 16 (old-style: VIB or VIA) in the periodic table. ... Organoselenium chemistry is the corresponding science exploring the properties and reactivity of organoselenium compounds – chemical compounds containing carbon to selenium bonds. ...

External links

  • Organosulfur chemistry at http://users.ox.ac.uk Link

References

  1. ^ Handbook of Chemistry and Physics, 81st Edition CRC Press ISBN 0-8493-0481-4
  2. ^ Organosulfur chemistry. reviews of current research JANSSEN, M.J. Interscience, New York,(1967)
  3. ^ For an example bis[2,2,2-trifluoro-1-phenyl-1-(trifluoromethyl) ethoxy] diphenyl sulfurane Organic Syntheses, Coll. Vol. 6, p.163 (1988); Vol. 57, p.22 (1977) Link.
  4. ^ Synthesis and characterization of hexamethyltellurium(VI) Latif Ahmed, John A. Morrison J. Am. Chem. Soc.; 1990; 112(20); 7411-7413. Abstract
  5. ^ The S6 Point Group Conformers of the Hexamethylchalcogens: Me6S, Me6Se, Me6Te Fowler, J. E.; Schaefer, H. F., III; Raymond, K. N. Inorg. Chem.; (Article); 1996; 35(2); 279-281. DOI:10.1021/ic940240d 10.1021/ic940240d
  6. ^ Isolation and Molecular Structure of the Organo-persulfuranes [12-S-6(C6)] Sato, S.; Matsunaga, K.; Horn, E.; Furukawa, N.; Nabeshima, T. J. Am. Chem. Soc.; (Communication); 2006; 128(21); 6778-6779. DOI:10.1021/ja060497y

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