tetracyanoquinodimethane

Also 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.

In the Vinony graph

Vinony's link graph records 20 inbound references to tetracyanoquinodimethane, and connects out to ion, electrical resistivity and conductivity and tetrathiafulvalene.

Vinony files it under Chembox having GHS data, Chembox image size set and Conjugated dienes.

Vinony links it to 12 Wikipedia language editions.

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 Å²
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

Sources (4)

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Encyclopedic overview

5 sections

Contents

Preparation and structure
Reactions
Charge transfer salts
Related compounds
References

==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.