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Thioketones
In organic chemistry, thioketones (; also known as thiones or thiocarbonyls) are organosulfur compounds related to conventional ketones in which the oxygen has been replaced by a sulfur. Instead of a structure of , thioketones have the structure , which is reflected by the prefix "thio-" in the name of the functional group. Unhindered alkylthioketones typically tend to form polymers or rings. Structure and bonding The C=S bond length of thiobenzophenone is 1.63 Å, which is comparable to 1.64 Å, the C=S bond length of thioformaldehyde, measured in the gas phase. Due to steric interactions, the phenyl groups are not coplanar and the dihedral angle SC-CC is 36°. Unhindered dialkylthiones polymerize or oligomerize but thiocamphor is well characterized red solid. Consistent with the double bond rule, most alkyl thioketones are unstable with respect to dimerization.Organosulfur Chemistry I: Topics in Current Chemistry, 1999, Volume 204/1999, 127-181, The energy difference between ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Thioketone Structural Formulae V
In organic chemistry, thioketones (; also known as thiones or thiocarbonyls) are organosulfur compounds related to conventional ketones in which the oxygen has been replaced by a sulfur. Instead of a structure of , thioketones have the structure , which is reflected by the prefix "thio-" in the name of the functional group. Unhindered alkylthioketones typically tend to form polymers or rings. Structure and bonding The C=S bond length of thiobenzophenone is 1.63 Å, which is comparable to 1.64 Å, the C=S bond length of thioformaldehyde, measured in the gas phase. Due to steric interactions, the phenyl groups are not coplanar and the dihedral angle SC-CC is 36°. Unhindered dialkylthiones polymerize or oligomerize but thio camphor is well characterized red solid. Consistent with the double bond rule, most alkyl thioketones are unstable with respect to dimerization.Organosulfur Chemistry I: Topics in Current Chemistry, 1999, Volume 204/1999, 127-181, The energy difference betwe ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Thioketones
In organic chemistry, thioketones (; also known as thiones or thiocarbonyls) are organosulfur compounds related to conventional ketones in which the oxygen has been replaced by a sulfur. Instead of a structure of , thioketones have the structure , which is reflected by the prefix "thio-" in the name of the functional group. Unhindered alkylthioketones typically tend to form polymers or rings. Structure and bonding The C=S bond length of thiobenzophenone is 1.63 Å, which is comparable to 1.64 Å, the C=S bond length of thioformaldehyde, measured in the gas phase. Due to steric interactions, the phenyl groups are not coplanar and the dihedral angle SC-CC is 36°. Unhindered dialkylthiones polymerize or oligomerize but thiocamphor is well characterized red solid. Consistent with the double bond rule, most alkyl thioketones are unstable with respect to dimerization.Organosulfur Chemistry I: Topics in Current Chemistry, 1999, Volume 204/1999, 127-181, The energy difference between ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Organosulfur Compound
Organosulfur compounds 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 abounds with organosulfur compounds—sulfur is vital for life. Of the 20 common amino acids, two ( cysteine and methionine) 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. Sulfur shares the chalcogen group with oxygen, selenium, and tellurium, and it is expected that organosulfur compounds have similarities with carbon–oxygen, carbon–selenium, and carbon–tellurium compounds. A classical chemical test for the detection of sulfur co ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Bis(trimethylsilyl)sulfide
Bis(trimethylsilyl) sulfide is the chemical compound with the formula ((CH3)3Si)2S. Often abbreviated ( tms)2S, this colourless, vile-smelling liquid is a useful aprotic source of "S2−" in chemical synthesis. Synthesis The reagent is prepared by treating trimethylsilyl chloride with anhydrous sodium sulfide: :2 (CH3)3SiCl + Na2S → ((CH3)3Si)2S + 2 NaCl ((CH3)3Si)2S must be protected from air because it hydrolyzes readily: :((CH3)3Si)2S + H2O → ((CH3)3Si)2O + H2S Use in synthesis Bis(trimethylsilyl)sulfide is a reagent for the conversion of metal oxides and chlorides into the corresponding sulfides. This transformation exploits the affinity of silicon(IV) for oxygen and halides. An idealized reaction is: :((CH3)3Si)2S + MO → ((CH3)3Si)2O + MS In a similar way, it has been used in the conversion of aldehyde In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (w ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Ph2CS
Thiobenzophenone is an organosulfur compound with the formula (C6H5)2CS. It is the prototypical thioketone. Unlike other thioketones that tend to dimerize to form rings and polymers, thiobenzophenone is quite stable, although it photoxidizes in air to form benzophenone and sulfur. Thiobenzophenone is deep blue and dissolves readily in many organic solvents. Structure The C=S bond length of thiobenzophenone is 1.63 Å, which is comparable to 1.64 Å, the C=S bond length of thioformaldehyde, measured in the gas phase. Due to steric interactions, the phenyl groups are not coplanar and the dihedral angle SC-CC is 36°.Sustmann, R.; Sicking, W.; Huisgen, R. "A Computational Study of the Cycloaddition of Thiobenzophenone S-Methylide to Thiobenzophenone". J. Am. Chem. Soc. 2003, 125, 14425-14434. A variety of thiones with structures and stability related to thiobenzophenone have also been prepared. Synthesis One of the first reported syntheses of thiobenzophenone involves the reaction ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Thioacetone
Thioacetone is an organosulfur compound belonging to the -thione group called thioketones, with a chemical formula (CH3)2CS. It is an unstable orange or brown substance that can be isolated only at low temperatures. Above , thioacetone readily converts to a polymer and a trimer, trithioacetone. It has an extremely potent, unpleasant odor, and is considered one of the worst-smelling chemicals known. Thioacetone was first obtained in 1889 by Baumann and Fromm, as a minor impurity in their synthesis of trithioacetone.William H. Sharkey (1979): "Polymerization through the carbon-sulfur double bond". ''Polymerization'', series ''Advances in Polymer Science'', volume 17, pages 73-103. Preparation Thioacetone is usually obtained by cracking the cyclic trimer trithioacetone, CH3)2CSsub>3. The trimer is prepared by pyrolysis of allyl isopropyl sulfide or by treating acetone with hydrogen sulfide in the presence of a Lewis acid. The trimer cracks at to give the thione. : Polymeri ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Thiobenzophenone
Thiobenzophenone is an organosulfur compound with the formula (C6H5)2CS. It is the prototypical thioketone. Unlike other thioketones that tend to dimerize to form rings and polymers, thiobenzophenone is quite stable, although it photoxidizes in air to form benzophenone and sulfur. Thiobenzophenone is deep blue and dissolves readily in many organic solvents. Structure The C=S bond length of thiobenzophenone is 1.63 Å, which is comparable to 1.64 Å, the C=S bond length of thioformaldehyde, measured in the gas phase. Due to steric interactions, the phenyl groups are not coplanar and the dihedral angle SC-CC is 36°.Sustmann, R.; Sicking, W.; Huisgen, R. "A Computational Study of the Cycloaddition of Thiobenzophenone S-Methylide to Thiobenzophenone". J. Am. Chem. Soc. 2003, 125, 14425-14434. A variety of thiones with structures and stability related to thiobenzophenone have also been prepared. Synthesis One of the first reported syntheses of thiobenzophenone involves the reaction ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Thioketene
In organic chemistry, thioketenes are organosulfur compounds analogous to ketenes with the general formula , where R is alkyl or aryl. Thioketene (ethenthione) is also the name of the compound , which is the simplest thioketene. Thioketenes are reactive, tending to polymerize. Some thioketenes are produced as transient species upon pyrolysis of 1,2,3-thiadiazoles. Bis(trifluoromethyl)thioketene () is a rare example of a stable thioketene. Another stable thioketene is carbon subsulfide Carbon subsulfide is an organic, sulfur-containing chemical compound with the formula and structure . This deep red liquid is immiscible with water but soluble in organic solvents. It readily polymerizes at room temperature to form a hard ... (). It has been suggested that thioketene could be involved in cell damage processes.{{cite journal , last1 = Dekant , first1 = Wolfgang , last2 = Urban , first2 = Gudrun , last3 = Goersmann , first3 =Claus, last4 = Anders , first4 = M.W. ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Thial
In organic chemistry, a thial or thioaldehyde is a functional group which is similar to an aldehyde, , in which a sulfur (S) atom replaces the oxygen (O) atom of the aldehyde (R represents an alkyl or aryl group). Thioaldehydes are even more reactive than thioketones. Unhindered thioaldehydes are generally too reactive to be isolated — for example, thioformaldehyde, , condenses to the cyclic trimer 1,3,5-trithiane. Thioacrolein, , formed by decomposition of allicin from garlic, undergoes a self Diels-Alder reaction giving isomeric vinyldithiins. While thioformaldehyde is highly reactive, it is found in interstellar space along with its mono- and di-deuterated isotopologues. With sufficient steric bulk, however, stable thioaldehydes can be isolated. In early work, the existence of thioaldehydes was inferred by trapping processes. For instance the reaction of with benzaldehyde was proposed to form thiobenzaldehyde, which forms a cycloadduct with the dithiophosphine ylides to ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Dithiirane
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 (). Structure According to electron diffraction, the and distances in ethylene sulfide are respectively 1.473 and 1.811 Å. The and angles are respectively 66.0 and 48.0°. Preparation History A number of chemists in the early 1900s, including Staudinger and Pfenninger (1916), as well as Delepine (1920) studied episulfides.Sander, M. Thiiranes. Chem. Rev. 1966, 66(3), 297-339. I 1934 Dachlauer and Jackel devised a general synthesis of episulfides from epoxides using alkali thiocyanates and thiourea. Contemporary methods Following the lead of Dach ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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