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thiepine

Structure via PubChem · Public domain (PubChem)

EntityQ417835· pop 20· linked from 14 articles

Also known as thiepin

In organic chemistry, thiepine (or thiepin) is an unsaturated seven-membered heterocyclic compound, with six carbon atoms and one sulfur atom. The parent compound, C6H6S is unstable and is predicted to be antiaromatic. Bulky derivatives have been isolated and shown by X-ray crystallography to have nonplanar C6S ring.

Chemical data

Formula
C6H6S
Molecular weight
110.18 g/mol
IUPAC name
thiepine
SMILES
C1=CC=CSC=C1
InChIKey
BISQTCXKVNCDDA-UHFFFAOYSA-N
XLogP
2.2
Polar surface area
25.3 Ų
H-bond donors
0
H-bond acceptors
1
Formal charge
0

via PubChem

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Encyclopedic overview

3 sections
Contents
  • See also
  • References
  • External links

In organic chemistry, thiepine (or thiepin) is an unsaturated seven-membered heterocyclic compound, with six carbon atoms and one sulfur atom. The parent compound, C6H6S is unstable and is predicted to be antiaromatic. Bulky derivatives have been isolated and shown by X-ray crystallography to have nonplanar C6S ring.

Computational studies suggest that thiepine would eliminate a sulfur atom to form benzene. The intermediate is this process is the bicycle thianorcaradiene. In the complex with (η4-C6H6S)Fe(CO)3, the ring is stable.

Excerpted from Wikipedia’s “thiepine” article, available under the CC BY-SA 4.0 licence.

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