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
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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
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 |
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
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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 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 |
Mass spectrum (electron ionization)
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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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Japan AIST/NIMC Database- Spectrum MS-NW- 597 |
NIST MS number | 229070 |
UV/Visible spectrum
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Spectrum
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Additional Data
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Source | Schurz and Ullrich, 1959 |
---|---|
Owner | INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
Origin | INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS |
Source reference | RAS UV No. 12875 |
Instrument | n.i.g. |
Melting point | 32 |
Boiling point | 218.5 |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, 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]
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]
Schurz and Ullrich, 1959
Schurz, J.; Ullrich, A.,
Z. physik. Chem. (Frankfurt), 1959, 21, 185. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, References
- Symbols used in this document:
IE (evaluated) Recommended ionization energy ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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