Butanedinitrile
- Formula: C4H4N2
- Molecular weight: 80.0880
- IUPAC Standard InChIKey: IAHFWCOBPZCAEA-UHFFFAOYSA-N
- CAS Registry Number: 110-61-2
- 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: Succinonitrile; s-Dicyanoethane; Deprelin; Dician; Dinile; Disuxyl; Ethane, 1,2-dicyano-; Ethylene cyanide; Ethylene dicyanide; Evanex; Succinic acid dinitrile; Succinic acid nitrile; Succinic dinitrile; Succinil; Succinodinitrile; Suxil; 1,2-Dicyanoethane; NCCH2CH2CN; USAF A-9442; 1,4-Butanedinitrile; Sukcinonitril; sym-Dicyanoethane; NSC 4852
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, References, Notes
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 50.11 ± 0.21 | kcal/mol | Ccr | Rapport, Westrum, et al., 1971 |
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°solid | 33.38 ± 0.16 | kcal/mol | Ccr | Rapport, Westrum, et al., 1971 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -546.22 ± 0.14 | kcal/mol | Ccr | Rapport, Westrum, et al., 1971 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°solid,1 bar | 45.791 | cal/mol*K | N/A | Wulff and Westrum, 1963 | crystaline, I phase; DH |
Constant pressure heat capacity of solid
Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
34.799 | 298.15 | Wulff and Westrum, 1963 | crystaline, I phase; T = 5 to 350 K.; DH |
Phase change data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, References, Notes
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
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 539.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 330. ± 5. | K | AVG | N/A | Average of 11 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 331.22 | K | N/A | Anonymous, 1988 | Uncertainty assigned by TRC = 0.005 K; nominal value, from the catalog; TRC |
Ttriple | 331.23 | K | N/A | Marsh, 1987 | Uncertainty assigned by TRC = 0.005 K; recommended as calibration standard; TRC |
Ttriple | 331.23 | K | N/A | Mangum and El-Sabban, 1985 | Uncertainty assigned by TRC = 0.0015 K; temp. on IPTS-68, as a triple point reference standard; TRC |
Ttriple | 331.16 | K | N/A | Wulff and Westrum, 1963, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 16.7 | kcal/mol | N/A | Rapport, Westrum, et al., 1971 | DRB |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
17. ± 0.07 | 289. | Woodman, Murbach, et al., 1960 | Based on data from 279. to 298. K. See also Pedley and Rylance, 1977, Westrum, Rapport, et al., 1971, and Stull, Westrum, et al., 1969.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
0.8853 | 334. | N/A | Rai, Singh, et al., 1987 | DH |
0.88 | 329.7 | DSC | Rai and Reddi, 2009 | AC |
0.896 | 330.3 | DSC | Badea, Blanco, et al., 2007 | AC |
0.88 | 331.2 | AC | Domalski and Hearing, 1996 | Based on data from 5. to 350. K. See also Wulff and Westrum, 1963.; AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
2.65 | 334. | Rai, Singh, et al., 1987 | DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
6.350 | 233.3 | Domalski and Hearing, 1996 | CAL |
2.679 | 331.2 |
Enthalpy of phase transition
ΔHtrs (kcal/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
1.4817 | 233.3 | crystaline, II | crystaline, I | Wulff and Westrum, 1963 | DH |
0.88511 | 331.16 | crystaline, I | liquid | Wulff and Westrum, 1963 | DH |
Entropy of phase transition
ΔStrs (cal/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
6.350 | 233.3 | crystaline, II | crystaline, I | Wulff and Westrum, 1963 | DH |
2.672 | 331.16 | crystaline, I | liquid | Wulff and Westrum, 1963 | DH |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Rapport, Westrum, et al., 1971
Rapport, N.J.; Westrum, E.F., Jr.; Andrews, J.T.S.,
Enthalpies of formation for globular molecules. III. Succinonitrile and triethylenediamine,
J. Am. Chem. Soc., 1971, 93, 4363-4365. [all data]
Wulff and Westrum, 1963
Wulff, C.A.; Westrum, E.F., Jr.,
Heat capacities and thermodynamic properties of globular molecules. VI. Succinonitrile,
J. Phys. Chem., 1963, 67, 2376-2381. [all data]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
Anonymous, 1988
Anonymous, X.,
, NBS Spec. Publ. (U. S.) 260, 1988. [all data]
Marsh, 1987
Marsh, K.N.,
Recommended Reference Materials for the Realization of Physicochemical Properties, Blackwell Sci. Pub., Oxford, 1987. [all data]
Mangum and El-Sabban, 1985
Mangum, B.W.; El-Sabban, S.,
SRM 1970: Succinotitrile Triple-Point Standard - A Temperature Reference Standard Near 58.08 C,
J. Res. Natl. Bur. Stand. (U. S.), 1985, 90, 359. [all data]
Wulff and Westrum, 1963, 2
Wulff, C.A.; Westrum, E.F.,
Heat capacities and thermodynamic properties of globular molecules: vi succinonitrile,
J. Phys. Chem., 1963, 67, 2376-81. [all data]
Woodman, Murbach, et al., 1960
Woodman, A.L.; Murbach, W.J.; Kaufman, M.H.,
Vapor pressure and viscosity relationships for a homologous series of α,omega-dinitriles,
Russ. J. Phys. Chem. (Engl. Transl.), 1960, 64, 658-660. [all data]
Pedley and Rylance, 1977
Pedley, J.B.; Rylance, J.,
, Computer Analysed Thermochemical Data: Organic and Organometallic Compounds, University of Sussex, Brighton, 1977. [all data]
Westrum, Rapport, et al., 1971
Westrum, Edgar F.; Rapport, Naomi J.; Andrews, John T.S.,
Enthalpies of formation for globular molecules III. Succinonitrile and triethylenediamine,
J. Am. Chem. Soc., 1971, 93, 18, 4363-4365, https://doi.org/10.1021/ja00747a005
. [all data]
Stull, Westrum, et al., 1969
Stull, D.R.; Westrum, E.F., Jr.; Sinke, G.C.,
The Chemical Thermodyanmics of Organic Compounds, John Wiley & Sons Inc., New York, 1969, 865. [all data]
Rai, Singh, et al., 1987
Rai, U.S.; Singh, O.P.; Singh, N.B.,
Some thermodynamic aspects of organic eutectics, succinonitrile-phenanthrene system,
Indian J. Chem., 1987, 26A, 947-949. [all data]
Rai and Reddi, 2009
Rai, R.N.; Reddi, R.S.B.,
Thermal, solid--liquid equilibrium, crystallization, and microstructural studies of organic monotectic alloy: 4,4´-Dibromobiphenyl--succinonitrile,
Thermochimica Acta, 2009, 496, 1-2, 13-17, https://doi.org/10.1016/j.tca.2009.06.012
. [all data]
Badea, Blanco, et al., 2007
Badea, Elena; Blanco, Ignazio; Della Gatta, Giuseppe,
Fusion and solid-to-solid transitions of a homologous series of alkane-α,ω-dinitriles,
The Journal of Chemical Thermodynamics, 2007, 39, 10, 1392-1398, https://doi.org/10.1016/j.jct.2007.03.005
. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, References
- 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 ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas 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 ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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