Propanedinitrile
- Formula: C3H2N2
- Molecular weight: 66.0614
- IUPAC Standard InChIKey: CUONGYYJJVDODC-UHFFFAOYSA-N
- CAS Registry Number: 109-77-3
- 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: Malononitrile; Cyanoacetonitrile; Dicyanomethane; Malonic acid dinitrile; Malonodinitrile; Methane, dicyano-; Methylene cyanide; Methylenedinitrile; CH2(CN)2; Malonitrile; Malonic dinitrile; Nitril kyseliny malonove; USAF A-4600; Dwumetylosulfotlenku; Rcra waste number U149; UN 2647; USAF KF-19; NSC 3769
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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 | 266.3 ± 1.0 | kJ/mol | Ccb | Beckhaus, Dogan, et al., 1990 | |
ΔfH°gas | 266. ± 2. | kJ/mol | Ccb | Boyd, Guha, et al., 1967 |
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 | 187.9 ± 0.2 | kJ/mol | Ccb | Beckhaus, Dogan, et al., 1990 | ALS |
ΔfH°solid | 186. ± 1. | kJ/mol | Ccb | Boyd, Guha, et al., 1967 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -1654.2 ± 0.2 | kJ/mol | Ccb | Beckhaus, Dogan, et al., 1990 | ALS |
ΔcH°solid | -1653. ± 1. | kJ/mol | Ccb | Boyd, Guha, et al., 1967 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°solid,1 bar | 130.96 | J/mol*K | N/A | Girdhar, Westrum, et al., 1968 | crystaline, I phase; Entropy as calculated from data on undercooled, c,I from 5 K and from data on c,II, c,II/c,I transition, and c,I is the same.; DH |
Constant pressure heat capacity of solid
Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
110.29 | 298.15 | Girdhar, Westrum, et al., 1968 | crystaline, I phase; T = 5 to 320 K.; DH |
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 493.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 491.7 | K | N/A | Weast and Grasselli, 1989 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 305. | K | N/A | Stephenson, 1994 | Uncertainty assigned by TRC = 2. K; TRC |
Tfus | 304. | K | N/A | Trunel, 1939 | Uncertainty assigned by TRC = 3. K; TRC |
Tfus | 307.6 | K | N/A | Van de Vloed, 1939 | Uncertainty assigned by TRC = 0.6 K; TRC |
Tfus | 304.65 | K | N/A | Bruhl, 1895 | Uncertainty assigned by TRC = 1.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 304.910 | K | N/A | Girdhar, Westrum, et al., 1968, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.06 K; TRC |
Ttriple | 304.980 | K | N/A | Girdhar, Westrum, et al., 1968, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC |
Ttriple | 304.99 | K | N/A | Westrum and Wulff, 1968 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 78.37 ± 0.96 | kJ/mol | C | Beckhaus, Dogan, et al., 1990 | ALS |
ΔsubH° | 78.4 | kJ/mol | N/A | Beckhaus, Dogan, et al., 1990 | DRB |
ΔsubH° | 78.2 ± 1.0 | kJ/mol | N/A | Beckhaus, Dogan, et al., 1990 | Based on data from 278. to 299. K.; AC |
ΔsubH° | 79.1 ± 0.8 | kJ/mol | V | Boyd, Guha, et al., 1967 | ALS |
ΔsubH° | 80.0 | kJ/mol | N/A | Boyd, Guha, et al., 1967 | DRB |
Reduced pressure boiling point
Tboil (K) | Pressure (bar) | Reference | Comment |
---|---|---|---|
382.2 | 0.027 | Weast and Grasselli, 1989 | BS |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
10.7 | 305. | DSC | Badea, Blanco, et al., 2007 | AC |
10.8 | 305. | N/A | Domalski and Hearing, 1996 | AC |
Temperature of phase transition
Ttrs (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|
140. | crystaline, IV, Re | crystaline, II, entrant phase transition; second order | Wasiutynski, Olejarczyk, et al., 1987 | DH |
303. | crystaline, I | crystaline, I' | Wasiutynski, Olejarczyk, et al., 1987 | First order transition.; DH |
260. | crystaline, III | crystaline, II | Wasiutynski, Olejarczyk, et al., 1987 | Phase III is stable below 260 K.; DH |
295. | crystaline, II | crystaline, I | Wasiutynski, Olejarczyk, et al., 1987 | Second order transition.; DH |
Enthalpy of phase transition
ΔHtrs (kJ/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
10.795 | 304.99 | crystaline, I | liquid | Girdhar, Westrum, et al., 1968 | DH |
Entropy of phase transition
ΔStrs (J/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
35.39 | 304.99 | crystaline, I | liquid | Girdhar, Westrum, et al., 1968 | DH |
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 as indicated in comments:
B - John E. Bartmess
MS - José A. Martinho Simões
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
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
C3HN2- + =
By formula: C3HN2- + H+ = C3H2N2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1405. ± 8.8 | kJ/mol | G+TS | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrH° | 1406. ± 11. | kJ/mol | G+TS | Cumming and Kebarle, 1978 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1373. ± 8.4 | kJ/mol | IMRE | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrG° | 1373. ± 8.4 | kJ/mol | IMRE | Cumming and Kebarle, 1978 | gas phase; B |
ΔrG° | 1376. ± 8.4 | kJ/mol | IMRE | Taft, Abboud, et al., 1988 | gas phase; Revised: 91TAF; B |
(solution) + C5H11BrMg (solution) = C3HBrMgN2 (solution) +
(solution)
By formula: C3H2N2 (solution) + C5H11BrMg (solution) = C3HBrMgN2 (solution) + C5H12 (solution)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -203.3 | kJ/mol | RSC | Holm, 1983 | solvent: Diethyl ether; MS |
By formula: I- + C3H2N2 = (I- • C3H2N2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 79.1 ± 4.2 | kJ/mol | TDAs | Caldwell, Masucci, et al., 1989 | gas phase; B,M |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Ion clustering data, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 12.8 ± 0.1 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 723.0 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 694.1 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
12.70 | PE | Molder, Pikver, et al., 1983 | LBLHLM |
12.88 | PE | Stafast and Bock, 1973 | LLK |
De-protonation reactions
C3HN2- + =
By formula: C3HN2- + H+ = C3H2N2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1405. ± 8.8 | kJ/mol | G+TS | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrH° | 1406. ± 11. | kJ/mol | G+TS | Cumming and Kebarle, 1978 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1373. ± 8.4 | kJ/mol | IMRE | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrG° | 1373. ± 8.4 | kJ/mol | IMRE | Cumming and Kebarle, 1978 | gas phase; B |
ΔrG° | 1376. ± 8.4 | kJ/mol | IMRE | Taft, Abboud, et al., 1988 | gas phase; Revised: 91TAF; B |
Ion clustering data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics 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:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.
Clustering reactions
By formula: I- + C3H2N2 = (I- • C3H2N2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 79.1 ± 4.2 | kJ/mol | TDAs | Caldwell, Masucci, et al., 1989 | gas phase; B,M |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Beckhaus, Dogan, et al., 1990
Beckhaus, H.D.; Dogan, B.; Pakusch, J.; Verevkin, S.; Ruechardt, C.,
Geminal substituent effects. 4. The dependence of the inverse anomeric effect of geminal cyano groups on the structure,
Chem. Ber., 1990, 123, 2153-2159. [all data]
Boyd, Guha, et al., 1967
Boyd, R.H.; Guha, K.R.; Wuthrich, R.,
Thermochemistry of cyanocarbons. II. The heats of combustion of pyridinium dicyanomethylide, malononitrile, and fumaronitrile,
J. Phys. Chem., 1967, 71, 2187-2191. [all data]
Girdhar, Westrum, et al., 1968
Girdhar, H.L.; Westrum, E.F., Jr.; Wulff, C.A.,
Thermodynamic properties and third-law cycle for malononitrile,
J. Chem. Eng. Data, 1968, 13, 239-242. [all data]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [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]
Stephenson, 1994
Stephenson, R.M.,
Mutual Solubility of Water and Nitriles,
J. Chem. Eng. Data, 1994, 39, 225-7. [all data]
Trunel, 1939
Trunel, P.,
Electric Moments in Several Homologous Series of Organic Compounds,
Ann. Chim. (Paris), 1939, 12, 110. [all data]
Van de Vloed, 1939
Van de Vloed, A.,
Bull. Soc. Chim. Belg., 1939, 48, 229. [all data]
Bruhl, 1895
Bruhl, J.W.,
Spectrochemistry of Nitrogen-Containing Compounds. I.,
Z. Phys. Chem., Stoechiom. Verwandtschaftsl., 1895, 16, 193. [all data]
Girdhar, Westrum, et al., 1968, 2
Girdhar, H.L.; Westrum, E.F.; Wulff, C.A.,
Thermodynamic properties and third-law cycle for malononitrile.,
J. Chem. Eng. Data, 1968, 13, 239-42. [all data]
Westrum and Wulff, 1968
Westrum, E.F.; Wulff, C.A.,
Thermodynamic properties and third-law cycle for malononitrile,
J. Chem. Eng. Data, 1968, 13, 239. [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]
Wasiutynski, Olejarczyk, et al., 1987
Wasiutynski, T.; Olejarczyk, W.; Sciesinski, J.; Witko, W.,
Phase transition studies of malononitrile,
J. Phys. C: Solid State Phys., 1987, 20, L65-L69. [all data]
Fujio, McIver, et al., 1981
Fujio, M.; McIver, R.T., Jr.; Taft, R.W.,
Effects on the acidities of phenols from specific substituent-solvent interactions. Inherent substituent parameters from gas phase acidities,
J. Am. Chem. Soc., 1981, 103, 4017. [all data]
Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P.,
Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A),
Can. J. Chem., 1978, 56, 1. [all data]
Taft, Abboud, et al., 1988
Taft, R.W.; Abboud, J.L.M.; Anvia, F.; Berthelot, M.; Fujio, M.; Gal, J.-F.; Headley, A.D.; Henderson, W.G.,
Regarding the Inherent Dependence of Resonance Effects of Strongly Conjugated Substituents on Electron Demand,
J. Am. Chem. Soc., 1988, 110, 6, 1797, https://doi.org/10.1021/ja00214a023
. [all data]
Holm, 1983
Holm, T.,
Acta Chem. Scand. B, 1983, 37, 797. [all data]
Caldwell, Masucci, et al., 1989
Caldwell, G.W.; Masucci, J.A.; Ikonomou, M.G.,
Negative Ion Chemical Ionization Mass Spectrometry - Binding of Molecules to Bromide and Iodide Anions,
Org. Mass Spectrom., 1989, 24, 1, 8, https://doi.org/10.1002/oms.1210240103
. [all data]
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [all data]
Molder, Pikver, et al., 1983
Molder, U.H.; Pikver, R.J.; Koppel, I.A.,
Photoelectron spectra of molecules. 3. Nitriles,
Org. React. Tartu, 1983, 20, 230. [all data]
Stafast and Bock, 1973
Stafast, H.; Bock, H.,
Photoelectron spectra molecular properties. XVII. Hyperconjugation in dicyanomethane and 2,2-dicyano propane,
Z. Naturforsch. B:, 1973, 28, 746. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid IE (evaluated) Recommended ionization energy S°solid,1 bar Entropy of solid at standard conditions (1 bar) Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature Ttrs Temperature of phase transition 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 ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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