2-Butynedinitrile
- Formula: C4N2
- Molecular weight: 76.0562
- IUPAC Standard InChI: InChI=1S/C4N2/c5-3-1-2-4-6
- IUPAC Standard InChIKey: ZEHZNAXXOOYTJM-UHFFFAOYSA-N
- CAS Registry Number: 1071-98-3
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
View 3d structure (requires JavaScript / HTML 5) - Other names: Acetylenedicarbonitrile; Dicyanoacetylene; 1,2-Dicyanoacetylene; NCC≡CCN; Dicyanoethyne; Sous-azote de carbone; C4N2
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Condensed phase thermochemistry data
Go To: Top, Phase change data, Reaction thermochemistry data, NIST Free Links, NIST Subscription Links, 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°liquid | 500.4 | kJ/mol | Ccb | Armstrong and Marantz, 1963 | Correction of Armstrong and Marantz, 1960 |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -2074.4 ± 1.3 | kJ/mol | Ccb | Armstrong and Marantz, 1963 | Reanalyzed by Cox and Pilcher, 1970, Original value = -2073. ± 0.8 kJ/mol; Correction of Armstrong and Marantz, 1960 |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -2156. | kJ/mol | Ccb | Moureu and Bongrand, 1920 |
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
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tboil | 349.7 | K | N/A | Weast and Grasselli, 1989 | BS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔvapH° | 28.9 | kJ/mol | N/A | Armstrong and Marantz, 1963 | DRB |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔsubH° | 44.246 | kJ/mol | V | Saggiomo, 1957 | Hfusion=3.700 kcal/mol; ALS |
Enthalpy of vaporization
| ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 27.3 | 310. | A | Stephenson and Malanowski, 1987 | Based on data from 295. to 350. K.; AC |
Enthalpy of sublimation
| ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 44.3 | 268. | I | SAGGIOMO, 1957 | Based on data from 263. to 273. K. See also Govers, 1975 and Stephenson and Malanowski, 1987.; AC |
Reaction 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
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.
Individual Reactions
+
= C24H16N2O
By formula: C4N2 + C20H14O = C24H16N2O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -129. | kJ/mol | Kin | Samuilov, Nurullina, et al., 1983 | liquid phase; solvent: Nonaquous |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, NIST Free Links, NIST Subscription Links, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Armstrong and Marantz, 1963
Armstrong, G.T.; Marantz, S.,
The heat of combustion of dicyanoacetylene [Correction Ref. 60ARM/MAR],
J. Phys. Chem., 1963, 67, 2888. [all data]
Armstrong and Marantz, 1960
Armstrong, G.T.; Marantz, S.,
The heat of combustion of dicyanoacetylene,
J. Phys. Chem., 1960, 64, 1776-1778. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Moureu and Bongrand, 1920
Moureu, M.C.; Bongrand, J.Ch.,
Thermochimie. - Nouvelles recherches sur le sous-azolure de carbone. Action des halogenes, des acides halohydriques et des alcools,
Compt. Rend., 1920, 170, 1025-1028. [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]
Saggiomo, 1957
Saggiomo, A.J.,
The dinitriles of acetylenedicarboxylic and polyacetylenedicarboxylic acids. I. Dicyanoacetylene and dicycanodiacetylene,
J. Org. Chem., 1957, 22, 1171. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
SAGGIOMO, 1957
SAGGIOMO, ANDREW J.,
The Dinitriles of Acetylenedicarboxylic and Polyacetylenedicarboxylic Acids. 1 I. 2 Dicyanoacetylene and Dicyanodiacetylene,
J. Org. Chem., 1957, 22, 10, 1171-1175, https://doi.org/10.1021/jo01361a009
. [all data]
Govers, 1975
Govers, H.A.J.,
Derivation of carbon--nitrogen, hydrogen--nitrogen and nitrogen--nitrogen non-bonded potential parameters in molecular crystals,
Acta Crystallogr Sect A Cryst Phys Diffr Theor Gen Crystallogr', 1975, 31, 3, 380-385, https://doi.org/10.1107/S0567739475000800
. [all data]
Samuilov, Nurullina, et al., 1983
Samuilov, Ya.D.; Nurullina, R.L.; Konovalov, A.I.,
Thermochemical and kinetic study of the Diels-Alder reaction with ethylene and acetylene dienophiles,
Zh. Org. Khim., 1983, 19, 1431-1435. [all data]
Notes
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- Symbols used in this document:
Tboil Boiling point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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