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thiobenzophenone
Sign in to saveThiobenzophenone 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 back to benzophenone and sulfur. Thiobenzophenone is deep blue and dissolves readily in many organic solvents.
Chemical data
- Formula
- C13H10S
- Molecular weight
- 198.29 g/mol
- IUPAC name
- diphenylmethanethione
- SMILES
- C1=CC=C(C=C1)C(=S)C2=CC=CC=C2
- InChIKey
- XDDVRYDDMGRFAZ-UHFFFAOYSA-N
- XLogP
- 3.5
- Polar surface area
- 32.1 Ų
- H-bond donors
- 0
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Has part
- sulfur
- Mass
- 198.050321
Show 3 more facts
- Commons category
- Thiobenzophenone
- chemical formula
- C₁₃H₁₀S
- canonical SMILES
- C1=CC=C(C=C1)C(=S)C2=CC=CC=C2
Sources (2)
via Wikidata · CC0
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Encyclopedic overview
4 sectionsContents
- Structure
- Synthesis
- Reactivity
- References
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 back to 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°. A variety of thiones with structures and stability related to thiobenzophenone have also been prepared.
Excerpted from Wikipedia’s “thiobenzophenone” article, available under the CC BY-SA 4.0 licence.