1,4-Benzenedicarbonitrile

Formula: C₈H₄N₂
Molecular weight: 128.1308
IUPAC Standard InChI: InChI=1S/C8H4N2/c9-5-7-1-2-8(6-10)4-3-7/h1-4H
IUPAC Standard InChIKey: BHXFKXOIODIUJO-UHFFFAOYSA-N
CAS Registry Number: 623-26-7
Chemical structure:
This structure is also available as a 2d Mol file
Other names: Terephthalonitrile; p-Benzenedinitrile; p-Dicyanobenzene; p-Phthalodinitrile; Terephthalic acid dinitrile; Terephthalodinitrile; 1,4-Dicyanobenzene; 4-Cyanobenzonitrile; Terephthalonitrile (di); p-Pdn; Nitril kyseliny tereftalove; Tereftalodinitril; 1,4-Benzodinitrile; 1,4-Benzendikarbonitril; Tereftalonitril; p-Phthalonitrile; p-Cyanobenzonitrile; NSC 144977; NSC 78439
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Gas phase thermochemistry data

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Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	358.3 ± 2.2	kJ/mol	Ccb	Acree, Tucker, et al., 1992	Author was aware that data differs from previously reported values
Δ_fH°_gas	357.1 ± 1.9	kJ/mol	Ccb	Sato-Toshima, Sakiyama, et al., 1980

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	268.5 ± 1.2	kJ/mol	Ccb	Acree, Tucker, et al., 1992	Author was aware that data differs from previously reported values; ALS
Δ_fH°_solid	268.3 ± 1.2	kJ/mol	Ccb	Sato-Toshima, Sakiyama, et al., 1980	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_solid	-3988.2 ± 0.6	kJ/mol	Ccb	Acree, Tucker, et al., 1992	Author was aware that data differs from previously reported values; ALS
Δ_cH°_solid	-3988.04 ± 0.59	kJ/mol	Ccb	Sato-Toshima, Sakiyama, et al., 1980	ALS
Quantity	Value	Units	Method	Reference	Comment
S°_{solid,1 bar}	183.0	J/mol*K	N/A	Lebedev, Bykova, et al., 1988	DH

Constant pressure heat capacity of solid

C_p,solid (J/mol*K)	Temperature (K)	Reference	Comment
161.2	298.15	Lebedev, Bykova, et al., 1988	T = 0 to 330 K.; DH

Phase change data

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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

Quantity	Value	Units	Method	Reference	Comment
T_triple	450.15	K	N/A	Lebedev, Bykova, et al., 1988	Uncertainty assigned by TRC = 1. K; TRC
Quantity	Value	Units	Method	Reference	Comment
Δ_subH°	89.3 ± 0.9	kJ/mol	AVG	N/A	Average of 6 values; Individual data points

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:

References

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

Acree, Tucker, et al., 1992
Acree, W.E., Jr.; Tucker, S.A.; Pilcher, G., Enthalpies of combustion of 1,4-dicyanobenzene di-N-oxide and 1,4-dicyanobenzene: the mean dissociation enthalpy of the (N-O) bonds, J. Chem. Thermodyn., 1992, 24, 213-216. [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]

Lebedev, Bykova, et al., 1988
Lebedev, B.V.; Bykova, T.A.; Kiparisova, Y.G.; Mitina, L.M.; Pankratov, V.A., Calorimetric study of terephthalodinitrile, its polycyclotrimerization, and the resulting polytriazine in the range 0-330 K, Vysokomol. Soedin., 1988, B30(3), 179-183. [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)
T_triple	Triple point temperature
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
Δ_subH°	Enthalpy of sublimation at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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