Propanedinitrile
- Formula: C3H2N2
- Molecular weight: 66.0614
- IUPAC Standard InChI: InChI=1S/C3H2N2/c4-2-1-3-5/h1H2
- 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
View 3d structure (requires JavaScript / HTML 5) - 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 | 63.64 ± 0.24 | kcal/mol | Ccb | Beckhaus, Dogan, et al., 1990 | |
| ΔfH°gas | 63.5 ± 0.5 | kcal/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 | 44.91 ± 0.05 | kcal/mol | Ccb | Beckhaus, Dogan, et al., 1990 | ALS |
| ΔfH°solid | 44.6 ± 0.3 | kcal/mol | Ccb | Boyd, Guha, et al., 1967 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -395.37 ± 0.05 | kcal/mol | Ccb | Beckhaus, Dogan, et al., 1990 | ALS |
| ΔcH°solid | -395.0 ± 0.3 | kcal/mol | Ccb | Boyd, Guha, et al., 1967 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°solid,1 bar | 31.300 | cal/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 (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 26.360 | 298.15 | Girdhar, Westrum, et al., 1968 | crystaline, I phase; T = 5 to 320 K.; DH |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
- LIQUID; Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY; 4 cm-1 resolution
- LIQUID (NEAT) $$PURITY 99.75%; BAIRD (PRISM); DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY
- SOLID (MULL, KEL-F OIL FOR 2-7.5 AND MINERAL OIL FOR 7.5-16 MICRONS); Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY; 4 cm-1 resolution
Vibrational and/or electronic energy levels
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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: Takehiko Shimanouchi
Symmetry: C2ν Symmetry Number σ = 2
| Sym. | No | Approximate | Selected Freq. | Infrared | Raman | Comments | ||||
|---|---|---|---|---|---|---|---|---|---|---|
| Species | type of mode | Value | Rating | Value | Phase | Value | Phase | |||
| a1 | 1 | CH2 s-str | 2935 | C | 2935 VS | liq. | 2929 | liq. | ||
| a1 | 2 | CN s-str | 2275 | C | 2275 M | liq. | 2263 | liq. | SF(ν9) | |
| a1 | 3 | CH2 scis | 1395 | C | 1395 VS | liq. | 1386 | liq. | ||
| a1 | 4 | CC s-str | 890 | C | 890 S | liq. | 892 | liq. | ||
| a1 | 5 | CCC deform | 582 | C | 582 M | liq. | 574 | liq. | ||
| a1 | 6 | CCN bend | 167 | C | 167 | liq. | ||||
| a2 | 7 | CH2 twist | 1220 | C | 1220 ia VW | liq. | 1214 | liq. | ||
| a2 | 8 | CCN bend | 367 | C | 371 ia M | liq. | 367 | liq. | SF(ν12) | |
| b1 | 9 | CN a-str | 2275 | C | 2275 M | liq. | 2263 | liq. | SF(ν2) | |
| b1 | 10 | CH2 wag | 1318 | C | 1318 W | liq. | 1310 | liq. | ||
| b1 | 11 | CC a-str | 982 | C | 982 S | liq. | 975 | liq. | ||
| b1 | 12 | CCN bend | 366 | C | 366 S | liq. | 367 | liq. | SF(ν8) | |
| b2 | 13 | CH2 a-str | 2968 | C | 2968 VS | liq. | 2960 | liq. | ||
| b2 | 14 | CH2 rock | 933 | C | 933 M | liq. | ||||
| b2 | 15 | CCN bend | 337 | C | 337 S | liq. | ||||
Source: Shimanouchi, 1972
Notes
| VS | Very strong |
| S | Strong |
| M | Medium |
| W | Weak |
| VW | Very weak |
| ia | Inactive |
| SF | Calculation shows that the frequency approximately equals that of the vibration indicated in the parentheses. |
| C | 3~6 cm-1 uncertainty |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, IR Spectrum, Vibrational and/or electronic energy levels, 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]
Shimanouchi, 1972
Shimanouchi, T.,
Tables of Molecular Vibrational Frequencies Consolidated Volume I, National Bureau of Standards, 1972, 1-160. [all data]
Notes
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- 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) 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 - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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