Tetracyano-p-quinodimethane

• Formula: C₁₂H₄N₄
• Molecular weight: 204.1870
• IUPAC Standard InChI: InChI=1S/C12H4N4/c13-5-11(6-14)9-1-2-10(4-3-9)12(7-15)8-16/h1-4H Copy

  
• IUPAC Standard InChIKey: PCCVSPMFGIFTHU-UHFFFAOYSA-N Copy
• CAS Registry Number: 1518-16-7
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  The 3d structure may be viewed using Java or Javascript.
• Other names: Propanedinitrile, 2,2'-(2,5-cyclohexadiene-1,4-diylidene)bis-; 2,5-Cyclohexadiene-δ1,α:4,α'-dimalononitrile; Quinodimethan, tetracyano-; Tetracyanoquinodimethan(e); TCNQ; 2,5-Cyclohexadiene-1,4-Diylidenedimalononitrile; 7,7,8,8-Tetracyano-p-quinodimethane; 7,7,8,8-Tetracyano-1,4-quinodimethan; 7,7,8,8-Tetracyanoquinodimethane; 7,7',8,8'-Tetracyanoquinodimethane; 2,5-Cyclohexadiene-1,4-diylidene-α,α'-dimalononitrile; Tetracyanoquinodimethan; NSC 105237; 2,2'-(2,5-cyclohexadiene-1,4-diylidene)bismalononitrile
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• Information on this page:
  • Phase change data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
• Data at other public NIST sites:
  • X-ray Photoelectron Spectroscopy Database, version 5.0
  • X-ray Photoelectron Spectroscopy Database, version 5.0
  • X-ray Photoelectron Spectroscopy Database, version 5.0
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Phase change data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos

Enthalpy of sublimation

References

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Metzger, Kuo, et al., 1983
Metzger, R.M.; Kuo, C.S.; Arafat, E.S., A semi-micro rotating-bomb combustion calorimeter, J. Chem. Thermodyn., 1983, 15, 841. [all data]

Boyd, 1963
Boyd, R.H., Thermochemistry of cyanocarbons, J. Chem. Phys., 1963, 38, 2529-2535. [all data]

Kersten and Oppermann, 1984
Kersten, von F.; Oppermann, H., Z. Phys. Chem. (Leipzig), 1984, 265, 1207. [all data]

de Kruif and Govers, 1980
de Kruif, C.G.; Govers, H.A.J., Enthalpies of sublimation and vapor pressures of 2,2´-bis-1,3-dithiole (TTF), 7,7,8,8-tetracyanoquinodimethane (TCNQ), and TTF--TCNQ (1:1), J. Chem. Phys., 1980, 73, 1, 553, https://doi.org/10.1063/1.439854 . [all data]

Swain, Kwan, et al., 1980
Swain, H.A.; Kwan, Chiu-Yin; Sung, Ho-Nan, Measurement of vapor pressures from 20 to 30.degree.C of long-chain peroxy acids, J. Phys. Chem., 1980, 84, 11, 1347-1349, https://doi.org/10.1021/j100448a012 . [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Boyd, 1963, 2
Boyd, Richard H., Thermochemistry of Cyanocarbons, J. Chem. Phys., 1963, 38, 10, 2529, https://doi.org/10.1063/1.1733536 . [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [all data]

Notes

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• Symbols used in this document:
  

  Tfus	Fusion (melting) point
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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