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tetracyanoquinodimethane
Sign in to saveAlso known as 2,5-Cyclohexadiene-1,4-diylidene-alpha,alpha'-dimalononitrile, 7,7',8,8'-Tetracyanoquinodimethane, 2,5-Cyclohexadiene-delta1,alpha:4,alpha'-dimalononitrile, Tetracyano-p-quinodimethane, 7,7,8,8-Tetracyanoquinodimethane, 7,7,8,8-Tetracyano-p-quinodimethane, 7,7,8,8-Tetracyano-1,4-quinodimethan, 2,5-Cyclohexadiene-delta(sup1alpha:4alpha)dimalononitrile
Tetracyanoquinodimethane (TCNQ) is an organic compound with the chemical formula . It is an orange crystalline solid. This cyanocarbon, a relative of para-quinone, is an electron acceptor that is used to prepare charge transfer salts, which are of interest in molecular electronics.
Chemical data
- Formula
- C12H4N4
- Molecular weight
- 204.19 g/mol
- IUPAC name
- 2-[4-(dicyanomethylidene)cyclohexa-2,5-dien-1-ylidene]propanedinitrile
- SMILES
- C1=CC(=C(C#N)C#N)C=CC1=C(C#N)C#N
- InChIKey
- PCCVSPMFGIFTHU-UHFFFAOYSA-N
- XLogP
- 1
- Polar surface area
- 95.2 Ų
- H-bond donors
- 0
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 204.044
Show 3 more facts
- canonical SMILES
- C1=CC(=C(C#N)C#N)C=CC1=C(C#N)C#N
- Commons category
- Tetracyanoquinodimethane
- chemical formula
- C₁₂H₄N₄
via Wikidata · CC0
~2 min read
Encyclopedic overview
5 sectionsContents
- Preparation and structure
- Reactions
- Charge transfer salts
- Related compounds
- References
Tetracyanoquinodimethane (TCNQ) is an organic compound with the chemical formula . It is an orange crystalline solid. This cyanocarbon, a relative of para-quinone, is an electron acceptor that is used to prepare charge transfer salts, which are of interest in molecular electronics.
==Preparation and structure== TCNQ is prepared by the condensation of 1,4-cyclohexanedione with malononitrile, followed by dehydrogenation of the resulting diene with bromine:
Excerpted from Wikipedia’s “tetracyanoquinodimethane” article, available under the CC BY-SA 4.0 licence.