- Sulfinyl chloride:
SOCl2
- Sulfoxide:
R2SO
- Sulfuryl chloride:
SO2Cl2
- Sulfone:
R2SOO
- Sulfonyl
chloride: RSO2Cl
Sulfinyl chloride
is the S(IV) compound as a source of chloride ions but
Sulfuryl chloride is the S(VI) compound as a source of chlorine.
Other names
of sulfinyl chloride
include sulfurous
oxychloride and thionyl chloride (the term of
sulfinyl is for the bivalent radical, -SO-, while sulfonyl refers to
-SO2 ). The molecule shape
of thionyl chloride
(SOCl2)
is tetrahedral, indicating the presence of a lone
pair of electrons on the S(IV) center, whereas that of phosgene ( COCl2)
is planar. In many reactions and chemical properties,
thionyl chloride is analogous to phosphoryl chloride
(phosphorus
oxychloride) which has three P-Cl bonds and one very strong P=O solid bond.
Sulfonates resemble carboxylates; -C(=O)- is replaced by -S(=O)2-.
Thionyl chloride is a clear to
yellow, fuming liquid, with pungent odour. It is corrosive and reactive liquid
with boiling point 76 C. It reacts with water violently to produce toxic fumes of
sulfur dioxide and hydrogen chloride and decomposes on heating above 140 C,
releasing toxic and corrosive fumes. It readily reacts with
amines and metals.
Thionyl chloride is prepared from the reaction of sulfur trioxide and
sulfur dichloride. It can be also obtained from the reaction between sulfur
dichloride and phosphorus chloride. Thionyl chloride is used as a chlorinating
agent in chemical reactions and as the positive active
material in lithium-thionyl chloride batteries. alkyl radicals into biologically
active molecules and thereby prevent their proper functioning. Thionyl chloride
has also been used
as a methylating agent which means a component in poison gases.
Thionyl chloride
is used in the organic synthesis include:
- the preparation of acid chlorides (
acyl chlorides,
sulfonyl
chlorides, phosphoryl
chlorides) which
are used to prepare many other derivatives
- Chlorination of alcohols to yield
alkyl chloride.
- Dehydration of
primary amides to produce isocyanides,
nitriles
and imidoyl
chlorides.
Sulfuryl
Chloride is the Sulfuric oxychloride
where as sulfinyl chloride is the sulfurous
oxychloride. Sulfuryl
Chloride is a colorless to yellowish liquid with a pungent odor. It boils at
69°C, decomposed by hot water and alkalies; soluble in most organic solvents
(benzene, chloroform,
carbon tetrachloride and acetic acid). It is not found in
nature due to strong hydrolysis. It is explosive also with donor solvents such as alcohols,
ethers, DMSO and DMF. It decompose at its boiling point.
It has two S-Cl single bonds and two S=O solid bonds.
It is prepared by the reaction of sulfur dioxide and chlorine in the presence of activated carbon. It is used as a solvent and as a
source of chlorine in chemical reactions. Sulfuryl chloride is useful
mainly in preparing pesticides. It is used as a chlorinating
(and sulfochlorinating) agent of alcohols, alkyls, aromatics, and epoxides
for the target molecules of pharmaceuticals,
disinfectants, dyestuffs, rayon, and poison gases. Chlorination in
organic synthesis with sulfuryl chloride is more selective than elementary
chlorine. It is useful to avoid secondary reactions. Chlorination of alcohols to yield
alkyl chloride.
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