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
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• 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:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • References
  • Notes
• Other data available:
  • 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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Gas phase thermochemistry 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:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Condensed phase thermochemistry 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Notes

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, 841-851. [all data]

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

Metzger, 1977
Metzger, R.M., The enthalpy of formation and the experimental crystal binding energy of tetrathiofulvalenium 7,7,8,8-tetracyanoquinodimethanide (TTF TCNQ), J. Chem. Phys., 1977, 66, 2525-2533. [all data]

Metzger, Kuo, et al., 1983, 2
Metzger, R.M.; Kuo, C.S.; Arafat, E.S., A semi-micro rotating-bomb combustion calorimeter, J. Chem. Thermodyn., 1983, 15, 841. [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
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  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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