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Organosulfur chemistry AI simulator
(@Organosulfur chemistry_simulator)
Hub AI
Organosulfur chemistry AI simulator
(@Organosulfur chemistry_simulator)
Organosulfur chemistry
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 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 compounds is the Carius halogen method.
Organosulfur compounds can be classified according to the sulfur-containing functional groups, which are listed (approximately) in decreasing order of their occurrence.
Sulfides, formerly known as thioethers, are characterized by C−S−C bonds Relative to C−C bonds, C−S bonds are both longer, because sulfur atoms are larger than carbon atoms, and about 10% weaker. Representative 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 (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). The single carbon to oxygen bond is shorter than that of the C−C bond. The bond dissociation energies for dimethyl sulfide and dimethyl ether are respectively 73 and 77 kcal/mol (305 and 322 kJ/mol).
Sulfides are typically prepared by alkylation of thiols. Alkylating agents include not only alkyl halides, but also epoxides, aziridines, and Michael acceptors.
They can also be prepared via the Pummerer rearrangement.
In the Ferrario reaction, phenyl ether is converted to phenoxathiin by action of elemental sulfur and aluminium chloride.
Organosulfur chemistry
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 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 compounds is the Carius halogen method.
Organosulfur compounds can be classified according to the sulfur-containing functional groups, which are listed (approximately) in decreasing order of their occurrence.
Sulfides, formerly known as thioethers, are characterized by C−S−C bonds Relative to C−C bonds, C−S bonds are both longer, because sulfur atoms are larger than carbon atoms, and about 10% weaker. Representative 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 (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). The single carbon to oxygen bond is shorter than that of the C−C bond. The bond dissociation energies for dimethyl sulfide and dimethyl ether are respectively 73 and 77 kcal/mol (305 and 322 kJ/mol).
Sulfides are typically prepared by alkylation of thiols. Alkylating agents include not only alkyl halides, but also epoxides, aziridines, and Michael acceptors.
They can also be prepared via the Pummerer rearrangement.
In the Ferrario reaction, phenyl ether is converted to phenoxathiin by action of elemental sulfur and aluminium chloride.