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Methylacrylonitrile

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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 by: Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
30.19298.15Mirzaliev, Shakhuradov, et al., 1987T = 253 to 353 K. Unsmoothed experimental datum given as 1.863 kJ/kg*K at 293 K. Cp(liq) = 2.2117 + 0.0056352T/K + 1.52x10-5T2/K2 kJ/kg*K (253 to 353 K). Note, second coefficient should be negative.

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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Kenneth Kroenlein director
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

Quantity Value Units Method Reference Comment
Tboil363.KN/AStephenson, 1994Uncertainty assigned by TRC = 3. K; TRC
Tboil363.5KN/AWeast and Grasselli, 1989BS

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
8.72288.AStephenson and Malanowski, 1987Based on data from 273. - 373. K.; AC
8.46243.N/AStull, 1947Based on data from 229. - 363. K.; AC

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (atm)
    T = temperature (K)

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Temperature (K) A B C Reference Comment
228.7 - 363.54.117841353.573-35.121Stull, 1947Coefficents calculated by NIST from author's data.

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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: John E. Bartmess

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

C4H4N- + Hydrogen cation = Methylacrylonitrile

By formula: C4H4N- + H+ = C4H5N

Quantity Value Units Method Reference Comment
Deltar370.7 ± 2.1kcal/molG+TSBartmess and Burnham, 1984gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar364.1 ± 2.0kcal/molIMREBartmess and Burnham, 1984gas phase; value altered from reference due to change in acidity scale

(CAS Reg. No. 42117-14-6 bullet 4294967295Methylacrylonitrile) + Methylacrylonitrile = CAS Reg. No. 42117-14-6

By formula: (CAS Reg. No. 42117-14-6 bullet 4294967295C4H5N) + C4H5N = CAS Reg. No. 42117-14-6

Quantity Value Units Method Reference Comment
Deltar50.7 ± 2.5kcal/molN/ABartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale

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 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
0.006288EFDDesfrancois, Abdoul-Carime, et al., 1994EA: 6.3 meV. Dipole-bound state.; B

Ionization energy determinations

IE (eV) Method Reference Comment
10.34PEWillett and Baer, 1980LLK
10.37 ± 0.02PEKoenig, Snell, et al., 1976Vertical value; LLK
10.37 ± 0.05PEHouk and Munchausen, 1976Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CH2N+12.05?PIWillett and Baer, 1980LLK
C2H3+13.20?PIWillett and Baer, 1980LLK
C2H3N+11.65C2H2EISakurai and Jennings, 1981LLK
C2H3N+11.65?PIWillett and Baer, 1980LLK
C3H2N+12.20?PIWillett and Baer, 1980LLK
C3H3+12.30?PIWillett and Baer, 1980LLK
C3H4+11.75?PIWillett and Baer, 1980LLK
C4H4N+12.55HPIWillett and Baer, 1980LLK

De-protonation reactions

C4H4N- + Hydrogen cation = Methylacrylonitrile

By formula: C4H4N- + H+ = C4H5N

Quantity Value Units Method Reference Comment
Deltar370.7 ± 2.1kcal/molG+TSBartmess and Burnham, 1984gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar364.1 ± 2.0kcal/molIMREBartmess and Burnham, 1984gas phase; value altered from reference due to change in acidity scale; B

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director


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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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 NIST Mass Spectrometry Data Center, 1998.
NIST MS number 291472

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


Gas Chromatography

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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

Kovats' RI, non-polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
CapillaryBPX-530.611.Aflalaye, Sternberg, et al., 199512. m/0.15 mm/0.25 «mu»m, H2
CapillaryBPX-530.614.Aflalaye, Sternberg, et al., 199512. m/0.15 mm/0.25 «mu»m, H2
CapillaryCP Sil 5 CB20.574.9Do and Raulin, 199225. m/0.15 mm/2. «mu»m, H2
CapillaryPoraPLOT Q100.560.Do and Raulin, 198910. m/0.32 mm/10. «mu»m, H2
CapillaryPoraPLOT Q160.560.Do and Raulin, 198910. m/0.32 mm/10. «mu»m, H2

Normal alkane RI, non-polar column, custom temperature program

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Column type Active phase I Reference Comment
CapillaryMethyl Silicone575.Zenkevich, 1999Program: not specified
CapillaryPolydimethyl siloxanes575.Zenkevich, 1997Program: not specified

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Mirzaliev, Shakhuradov, et al., 1987
Mirzaliev, A.A.; Shakhuradov, Sh.G.; Guseinov, S.O., Investigation of the isobaric heat capacity of nitriles at different temperatures, Izv. Vyssh. Ucheb. Zaved., Neft i Gaz, 1987, 30(4), 55-58. [all data]

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]

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]

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [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 «alpha»-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]

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, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, References