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Dimethyl sulfone (DMSO 2) is an organosulfur compound with the formula (CH 3) 2 SO 2. It is also known by several other names including methyl sulfone and (especially in alternative medicine) methylsulfonylmethane (MSM). [4] This colorless solid features the sulfonyl functional group and is the simplest of the sulfones. It is relatively inert ...
Methanesulfonyl chloride is mainly used to give methanesulfonates by its reaction with alcohols in the presence of a non-nucleophilic base. [8] In contrast to the formation of toluenesulfonates from alcohols and p-toluenesulfonyl chloride in the presence of pyridine, the formation of methanesulfonates is believed to proceed via a mechanism wherein methanesulfonyl chloride first undergoes an ...
The intermediate benzenesulfonic acid can be chlorinated with thionyl chloride as well. Benzenesulfonyl chloride, the most important sulfonyl halide, can also be produced by treating sodium benzenesulfonate with phosphorus pentachlorides. [5] Benzenediazonium chloride reacts with sulfur dioxide and copper(I) chloride to give the sulfonyl chloride:
The C−S bond dissociation energy for thiomethane is 89 kcal/mol (370 kJ/mol) compared to methane's 100 kcal/mol (420 kJ/mol) and when hydrogen is replaced by a methyl group the energy decreases to 73 kcal/mol (305 kJ/mol). [5] The single carbon to oxygen bond is shorter than that of the C−C bond.
In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula CH 3 (whereas normal methane has the formula CH 4). In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in many organic compounds. It is a very stable group in ...
Alkyl sulfones may be reduced with sodium or lithium in liquid ammonia; [11] however, the strongly basic conditions of these dissolving metal reductions represent a significant disadvantage. In alcoholic solvents, magnesium metal and a catalytic amount of mercury(II) chloride may be used. [12]
Treatment of sulfur with hydrogen gives hydrogen sulfide.When dissolved in water, hydrogen sulfide is mildly acidic: [5] H 2 S ⇌ HS − + H +. Hydrogen sulfide gas and the hydrosulfide anion are extremely toxic to mammals, due to their inhibition of the oxygen-carrying capacity of hemoglobin and certain cytochromes in a manner analogous to cyanide and azide.
Passage of hydrogen chloride through molten Ms 2 O yields MsCl. [3] Similar to MsCl, Ms 2 O can perform mesylation of alcohols to form sulfonates. Use of Ms 2 O avoids the alkyl chloride, which often appears as a side-product when MsCl is used. [4] Unlike MsCl, Ms 2 O may not be suitable for mesylation of the unsaturated alcohols. [5]