Tetrathiafulvalene

• Formula: C₆H₄S₄
• Molecular weight: 204.356
• IUPAC Standard InChI: InChI=1S/C6H4S4/c1-2-8-5(7-1)6-9-3-4-10-6/h1-4H Copy

  
• IUPAC Standard InChIKey: FHCPAXDKURNIOZ-UHFFFAOYSA-N Copy
• CAS Registry Number: 31366-25-3
• 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: 1,3-Dithiole, 2-(1,3-dithiol-2-ylidene)-; Δ2,2'-Bi-1,3-dithiole; 1,4,5,8-Tetrathiafulvalene; δ-2:2'-bis(1,3-dithiazole)
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• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • References
  • Notes
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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

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 by: William E. Acree, Jr., James S. Chickos

Enthalpy of vaporization

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 as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy 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

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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, 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]

Dykyj, Svoboda, et al., 1999
Dykyj, J.; Svoboda, J.; Wilhoit, R.C.; Frenkel, M.L.; Hall, K.R., Vapor Pressure of Chemicals: Part A. Vapor Pressure and Antoine Constants for Hydrocarbons and Sulfur, Selenium, Tellurium and Hydrogen Containing Organic Compounds, Springer, Berlin, 1999, 373. [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]

Sandman, Epstein, et al., 1979
Sandman, D.J.; Epstein, A.J.; Chickos, J.S.; Ketchum, J.; Fu, J.S.; Scheraga, H.A., Crystal lattice and polarization energy of tetrathiafulvalene, J. Chem. Phys., 1979, 70, 1, 305, https://doi.org/10.1063/1.437191 . [all data]

Kobayashi, Yoshida, et al., 1984
Kobayashi, T.; Yoshida, Z.; Awaji, H.; Kawase, T.; Ioneda, S., Intramolecular orbital interaction in 6,6'-bi(1,4-dithiafulvenyl) studied by photoelectron spectroscopy, Bull. Chem. Soc. Jpn., 1984, 57, 2591. [all data]

Engler, Kaufman, et al., 1975
Engler, E.M.; Kaufman, F.B.; Green, D.C.; Klots, C.E.; Compton, R.N., Ionization potentials and donor properties of selenium analogs of tetrathiafulvalene, J. Am. Chem. Soc., 1975, 97, 2921. [all data]

Gleiter, Kobayashi, et al., 1975
Gleiter, R.; Kobayashi, M.; Spanget-Larsen, J.; Ferraris, J.P.; Bloch, A.N.; Bechgaard, K.; Cowan, D.O., Photoelectron and electronic absorption spectra of tetrathiafulvalene and related compounds, Ber. Bunsen-Ges. Phys. Chem., 1975, 79, 1218. [all data]

Berlinsky, Carolan, et al., 1974
Berlinsky, A.J.; Carolan, J.F.; Weiler, L., Photoelectron spectrum and electronic structure of tetrathiofulvalene (TTF), Can. J. Chem., 1974, 52, 3373. [all data]

Gleiter, Schmidt, et al., 1973
Gleiter, R.; Schmidt, E.; Cowan, D.O.; Ferraris, J.P., The electronic structure of tetrathiofulvalene, J. Electron Spectrosc. Relat. Phenom., 1973, 2, 207. [all data]

Notes

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• Symbols used in this document:
  

  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔsubH	Enthalpy of sublimation
  ΔvapH	Enthalpy of vaporization

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