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:
  • Condensed phase thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Phase change 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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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

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

References

Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics 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]

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]

Boyd, 1963
Boyd, R.H., Thermochemistry of cyanocarbons, J. Chem. Phys., 1963, 38, 2529-2535. [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, Condensed phase thermochemistry data, Gas phase ion energetics data, References

• Symbols used in this document:
  

  EA	Electron affinity
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions

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