1,2-Benzenedicarbonitrile

• Formula: C₈H₄N₂
• Molecular weight: 128.1308
• IUPAC Standard InChI: InChI=1S/C8H4N2/c9-5-7-3-1-2-4-8(7)6-10/h1-4H Copy

  
• IUPAC Standard InChIKey: XQZYPMVTSDWCCE-UHFFFAOYSA-N Copy
• CAS Registry Number: 91-15-6
• 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: Phthalonitrile; o-Benzenedicarbonitrile; o-Cyanobenzonitrile; o-Dicyanobenzene; Phthalodinitrile; 1,2-Dicyanobenzene; o-Phthalodinitrile; o-PDN; Phthalic acid dinitrile; USAF ND-09; 1,2-Benzodinitrile; 1,2-Benzendikarbonitril; Ftalodinitril; Ftalonitril; o-Benzenedinitrile; NSC 17562
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• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • Gas Chromatography
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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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of solid

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:
BS - Robert L. Brown and Stephen E. Stein
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
DH - Eugene S. Domalski and Elizabeth D. Hearing

Reduced pressure boiling point

Enthalpy of fusion

Entropy of fusion

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.

Rabinovich, Karyakin, et al., 1984
Rabinovich, I.B.; Karyakin, N.V.; Dzharimova, E.S.; Siling, S.A.; Ponomarev, I.I.; Vinogradova, S.V., Thermodynamics of condensation of phthalonitrile with m-phenylenediamine, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1984, 716-723. [all data]

Sato-Toshima, Sakiyama, et al., 1980
Sato-Toshima, T.; Sakiyama, M.; Seki, S., Thermochemical estimation of destabilization energies of 1,2-, 1,3-, and 1,4-dicyanobenzenes due to interactions between substituents. Appendix: Dipole moments in solution of the dicyanobenzenes, Bull. Chem. Soc. Jpn., 1980, 53, 2762-2767. [all data]

Salley and Gray, 1951
Salley, D.J.; Gray, J.B., Heats of combustion of some organic nitrogen compounds, J. Am. Chem. Soc., 1951, 73, 5925. [all data]

Salley and Gray, 1948
Salley, D.J.; Gray, J.B., Heats of combustion of some organic nitrogen compounds, J. Am. Chem. Soc., 1948, 70, 2650-2653. [all data]

Rabinovich, Karyakin, et al., 1984, 2
Rabinovich, I.B.; Karyakin, N.V.; Dzharimova, E.S.; Siling, S.A.; Ponomarev, I.I.; Vinogradova, S.V., Thermodynamics of the condensation of o-phthalic acid dinitrile with m-phenylenediamine, Izv. Akad. Nauk SSSR, Ser. Khim., 1984, (4), 779-787. [all data]

Karyakin, Shvetsova, et al., 1982
Karyakin, N.V.; Shvetsova, K.G.; Dzharimova, E.S., Thermodynamic properties of o-phthalic acid dinitrile, 1982, Termodin. [all data]

Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M., Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [all data]

Witschonke, 1954
Witschonke, C.R., Freezing point and purity data for some organic compounds, Anal. Chem., 1954, 26, 562-4. [all data]

Rabinovich, Nistratov, et al., 1984
Rabinovich, I.B.; Nistratov, V.P.; Babinkov, A.G.; Siling, S.A.; Ponomarev, I.I.; Vinogradova, S.V., Thermodynamics of the condensation of o-phthalic acid dinitrile with m-phenylenediamine, Izv. Akad. Nauk SSSR, 1984, 1984, 779. [all data]

Karyikin, Shvetsova, et al., 1982
Karyikin, N.V.; Shvetsova, K.G.; Dzharimova, E.S., Thermodynamic properties of o-phthalic acid dinitrile, Termodin. Org. Soedin., 1982, 33-37. [all data]

Karyakin, Shvetsova, et al., 1982, 2
Karyakin, N.V.; Shvetsova, K.G.; Dzharimova, E.S., Termodin. Org. Soedin., 1982, 33. [all data]

Notes

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• Symbols used in this document:
  

  Cp,solid	Constant pressure heat capacity of solid
  S°solid,1 bar	Entropy of solid at standard conditions (1 bar)
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔsubH°	Enthalpy of sublimation at standard conditions

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