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
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • References
  • Notes
• 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

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References, Notes

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

Gas phase ion energetics 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: John E. Bartmess

Electron affinity determinations

Mass spectrum (electron ionization)

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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]

Compton and Cooper, 1977
Compton, R.N.; Cooper, C.D., Negative ion properties of tetracyanoquinodimethane: Electron affinity and compound states, J. Chem. Phys., 1977, 66, 4325. [all data]

Klots, Compton, et al., 1974
Klots, C.E.; Compton, R.N.; Raaen, V.F., Electronic and ionic properties of of molecular TTF and TCMQ, J. Chem. Phys., 1974, 60, 1177. [all data]

Brinkman, Gunther, et al., 1994
Brinkman, E.A.; Gunther, E.; Schafer, O.; Brauman, J.I., Bound Excited Electronic States of Anions, J. Chem. Phys., 1994, 100, 3, 1840, https://doi.org/10.1063/1.466535 . [all data]

Nazarenko and Pokhodenko, 1979
Nazarenko, V.A.; Pokhodenko, V.D., The formation of negative ions in high electric fields, Int. J. Mass Spectrom. Ion Phys., 1979, 31, 381. [all data]

Farragher and Page, 1967
Farragher, A.L.; Page, F.M., Experimental Determination of Electron Affinities. Part 11. - Electron Capture by Some Cyanocarbons and Related Compounds, Trans. Farad. Soc., 1967, 63, 2369, https://doi.org/10.1039/tf9676302369 . [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References

• Symbols used in this document:
  

  EA	Electron affinity
  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

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