Methylacrylonitrile
- Formula: C4H5N
- Molecular weight: 67.0892
- IUPAC Standard InChIKey: GYCMBHHDWRMZGG-UHFFFAOYSA-N
- CAS Registry Number: 126-98-7
- 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: 2-Propenenitrile, 2-methyl-; Methacrylonitrile; α-Methacrylonitrile; α-Methylacrylonitrile; Isopropene cyanide; Isopropenylnitrile; 2-Cyano-1-propene; 2-Cyanopropene; 2-Methyl-2-propenenitrile; 2-Methylacrylonitrile; 2-Methylpropenenitrile; CH2C(CH3)CN; 2-Cyanopropene-1; USAF ST-40; Rcra waste number U152; 1-Methyl-1-cyanoethylene; Propenenitrile, 2-methyl; NSC 24145
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Phase change data
Go To: Top, Gas phase ion energetics data, Gas Chromatography, 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 363. | K | N/A | Stephenson, 1994 | Uncertainty assigned by TRC = 3. K; TRC |
Tboil | 363.5 | K | N/A | Weast and Grasselli, 1989 | BS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
36.5 | 288. | A | Stephenson and Malanowski, 1987 | Based on data from 273. to 373. K.; AC |
35.4 | 243. | N/A | Stull, 1947 | Based on data from 229. to 363. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
228.7 to 363.5 | 4.12355 | 1353.573 | -35.121 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Gas phase ion energetics data
Go To: Top, Phase change data, Gas Chromatography, 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
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
0.006288 | EFD | Desfrancois, Abdoul-Carime, et al., 1994 | EA: 6.3 meV. Dipole-bound state.; B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
10.34 | PE | Willett and Baer, 1980 | LLK |
10.37 ± 0.02 | PE | Koenig, Snell, et al., 1976 | Vertical value; LLK |
10.37 ± 0.05 | PE | Houk and Munchausen, 1976 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CH2N+ | 12.05 | ? | PI | Willett and Baer, 1980 | LLK |
C2H3+ | 13.20 | ? | PI | Willett and Baer, 1980 | LLK |
C2H3N+ | 11.65 | C2H2 | EI | Sakurai and Jennings, 1981 | LLK |
C2H3N+ | 11.65 | ? | PI | Willett and Baer, 1980 | LLK |
C3H2N+ | 12.20 | ? | PI | Willett and Baer, 1980 | LLK |
C3H3+ | 12.30 | ? | PI | Willett and Baer, 1980 | LLK |
C3H4+ | 11.75 | ? | PI | Willett and Baer, 1980 | LLK |
C4H4N+ | 12.55 | H | PI | Willett and Baer, 1980 | LLK |
De-protonation reactions
C4H4N- + =
By formula: C4H4N- + H+ = C4H5N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1551. ± 8.8 | kJ/mol | G+TS | Bartmess and Burnham, 1984 | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1523. ± 8.4 | kJ/mol | IMRE | Bartmess and Burnham, 1984 | gas phase; value altered from reference due to change in acidity scale; B |
Gas Chromatography
Go To: Top, Phase change 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | BPX-5 | 30. | 611. | Aflalaye, Sternberg, et al., 1995 | 12. m/0.15 mm/0.25 μm, H2 |
Capillary | BPX-5 | 30. | 614. | Aflalaye, Sternberg, et al., 1995 | 12. m/0.15 mm/0.25 μm, H2 |
Capillary | CP Sil 5 CB | 20. | 574.9 | Do and Raulin, 1992 | 25. m/0.15 mm/2. μm, H2 |
Capillary | PoraPLOT Q | 100. | 560. | Do and Raulin, 1989 | 10. m/0.32 mm/10. μm, H2 |
Capillary | PoraPLOT Q | 160. | 560. | Do and Raulin, 1989 | 10. m/0.32 mm/10. μm, H2 |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Methyl Silicone | 575. | Zenkevich, 1999 | Program: not specified |
Capillary | Polydimethyl siloxanes | 575. | Zenkevich, 1997 | Program: not specified |
References
Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Stephenson, 1994
Stephenson, R.M.,
Mutual Solubility of Water and Nitriles,
J. Chem. Eng. Data, 1994, 39, 225-7. [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 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]
Stull, 1947
Stull, Daniel R.,
Vapor Pressure of Pure Substances. Organic and Inorganic Compounds,
Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022
. [all data]
Desfrancois, Abdoul-Carime, et al., 1994
Desfrancois, C.; Abdoul-Carime, H.; Khelifa, N.; Schermann, J.P.,
Fork 1/r to 1/r2 Potentials: Electron Exchange between Rydberg Atoms and Polar Molecules,
Phys. Rev. Lett., 1994, 73, 18, 2436, https://doi.org/10.1103/PhysRevLett.73.2436
. [all data]
Willett and Baer, 1980
Willett, G.D.; Baer, T.,
Thermochemistry and dissociation dynamics of state-selected C4H4X ions. 3. C4H5N+,
J. Am. Chem. Soc., 1980, 102, 6774. [all data]
Koenig, Snell, et al., 1976
Koenig, T.; Snell, W.; Chang, J.C.,
The He(I) photoelectron spectra of benzyl and α-cyanoisopropyl radicals,
Tetrahedron Lett., 1976, 50, 4569. [all data]
Houk and Munchausen, 1976
Houk, K.N.; Munchausen, L.L.,
Ionization potentials, electron affinities, reactivities of cyanoalkenes related electron-deficient alkenes. A frontier molecular orbital treatment of cyanoalkene reactivities in cycloaddition, electrophilic, nucleophilic, and radical reactions.,
J. Am. Chem. Soc., 1976, 98, 937. [all data]
Sakurai and Jennings, 1981
Sakurai, H.; Jennings, K.R.,
A study of the structures of decomposing and non-decomposing [C4H5N]+ ions formed from different neutral species,
Org. Mass Spectrom., 1981, 16, 393. [all data]
Bartmess and Burnham, 1984
Bartmess, J.E.; Burnham, R.,
Effect of central substituents on the gas phase acidities of propenes,
J. Org. Chem., 1984, 49, 1382. [all data]
Aflalaye, Sternberg, et al., 1995
Aflalaye, A.; Sternberg, R.; Raulin, F.; Vidal-Madjar, C.,
Gas chromatography of Titan's atmosphere. VI. Analysis of low-molecular-mass hydrocarbons and nitriles with BPX5 capillary columns,
J. Chromatogr. A, 1995, 708, 2, 283-291, https://doi.org/10.1016/0021-9673(95)00410-O
. [all data]
Do and Raulin, 1992
Do, L.; Raulin, F.,
Gas chromatography of Titan's atmosphere. III. Analysis of low-molecular-weight hydrocarbons and nitriles with a CP-Sil-5 CB WCOT capillary column,
J. Chromatogr., 1992, 591, 1-2, 297-301, https://doi.org/10.1016/0021-9673(92)80247-R
. [all data]
Do and Raulin, 1989
Do, L.; Raulin, F.,
Gas chromatography of Titan's atmosphere. I. Analysis of low-molecular-weight hydrocarbons and nitriles with a PoraPLOT Q porous polymer coated open-tubular capillary column,
J. Chromatogr., 1989, 481, 45-54, https://doi.org/10.1016/S0021-9673(01)96751-2
. [all data]
Zenkevich, 1999
Zenkevich, I.G.,
New Application of the Retention Index Concept in Gas and High Performance Liquid Chromatography,
Fresenius' J. Anal. Chem., 1999, 365, 4, 305-309, https://doi.org/10.1007/s002160051491
. [all data]
Zenkevich, 1997
Zenkevich, I.G.,
Influence of the Variations of Dynamics Molecular Parameterts on the Additivity of Chromatigraphic Retention Indices of Products of Organic Reactions Relative to Initial Reagents,
Dokl. Akad. Nauk (Rus.), 1997, 353, 5, 625-627. [all data]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy EA Electron affinity Tboil Boiling point ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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