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
IUPAC Standard InChIKey: XQZYPMVTSDWCCE-UHFFFAOYSA-N
CAS Registry Number: 91-15-6
Chemical structure:
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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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Gas phase thermochemistry data

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Data compiled as indicated in comments:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	368.3	kJ/mol	N/A	Rabinovich, Karyakin, et al., 1984	Value computed using Δ_fH_solid° value of 281.4±1.9 kj/mol from Rabinovich, Karyakin, et al., 1984 and Δ_subH° value of 86.9 kj/mol from Rabinovich, Karyakin, et al., 1984.; DRB
Δ_fH°_gas	367.5 ± 1.9	kJ/mol	Ccb	Sato-Toshima, Sakiyama, et al., 1980	ALS
Δ_fH°_gas	362.0	kJ/mol	N/A	Salley and Gray, 1951	Value computed using Δ_fH_solid° value of 275.1 kj/mol from Salley and Gray, 1951 and Δ_subH° value of 86.9 kj/mol from Salley and Gray, 1951.; DRB

Condensed phase thermochemistry data

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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

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_solid	281.4 ± 1.9	kJ/mol	Ccb	Rabinovich, Karyakin, et al., 1984	Heat of combustion is not reported; ALS
Δ_fH°_solid	280.6 ± 1.2	kJ/mol	Ccb	Sato-Toshima, Sakiyama, et al., 1980	ALS
Δ_fH°_solid	275.1	kJ/mol	Ccb	Salley and Gray, 1951	correction of Salley and Gray, 1948; ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_solid	-4000.36 ± 0.67	kJ/mol	Ccb	Sato-Toshima, Sakiyama, et al., 1980	ALS
Δ_cH°_solid	-3994.9	kJ/mol	Ccb	Salley and Gray, 1951	correction of Salley and Gray, 1948; ALS
Quantity	Value	Units	Method	Reference	Comment
S°_{solid,1 bar}	192.4	J/mol*K	N/A	Rabinovich, Karyakin, et al., 1984, 2	DH
S°_{solid,1 bar}	192.4	J/mol*K	N/A	Karyakin, Shvetsova, et al., 1982	DH

Constant pressure heat capacity of solid

C_p,solid (J/mol*K)	Temperature (K)	Reference	Comment
161.3	298.15	Rabinovich, Karyakin, et al., 1984, 2	T = 13 to 500 K.; DH
161.3	298.15	Karyakin, Shvetsova, et al., 1982	T = 13 to 480 K.; DH

References

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

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]

Notes

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Symbols used in this document:

C_p,solid	Constant pressure heat capacity of solid
S°_{solid,1 bar}	Entropy of solid at standard conditions (1 bar)
Δ_cH°_solid	Enthalpy of combustion of solid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_solid	Enthalpy of formation of solid at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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