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Acetic acid, cyano-, methyl ester

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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
Deltafgas-58.15 ± 0.25kcal/molCcbVerevkin, Beckhaus, et al., 1995 

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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafliquid-73.98 ± 0.13kcal/molCcbVerevkin, Beckhaus, et al., 1995 
Deltafliquid-74.6kcal/molCcbGuinchant, 1918Author hf288_condensed[kcal/mol]=-77.8 kcal/mol
Quantity Value Units Method Reference Comment
Deltacliquid-473.02 ± 0.11kcal/molCcbVerevkin, Beckhaus, et al., 1995 
Deltacliquid-472.4kcal/molCcbGuinchant, 1918Author hf288_condensed[kcal/mol]=-77.8 kcal/mol

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
AC - William E. Acree, Jr., James S. Chickos

Quantity Value Units Method Reference Comment
Tboil478.7KN/AAldrich Chemical Company Inc., 1990BS
Tboil473.7KN/AWeast and Grasselli, 1989BS
Quantity Value Units Method Reference Comment
Tfus260.0KN/ADreisbach, 1955Uncertainty assigned by TRC = 0.02 K; TRC
Quantity Value Units Method Reference Comment
Deltavap15.83 ± 0.21kcal/molVVerevkin, Beckhaus, et al., 1995ALS
Deltavap15.8 ± 0.2kcal/molGSVerevkin, Beckhaus, et al., 1995Based on data from 292. - 322. K.; AC
Deltavap13.4 ± 1.0kcal/molEGuthrie and Cullimore, 1980ALS

Reduced pressure boiling point

Tboil (K) Pressure (atm) Reference Comment
388.20.047Weast and Grasselli, 1989BS

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
13.1400.AStephenson and Malanowski, 1987Based on data from 385. - 573. K. See also Dykyj, 1971.; AC

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 as indicated in comments:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

C4H4NO2- + Hydrogen cation = Acetic acid, cyano-, methyl ester

By formula: C4H4NO2- + H+ = C4H5NO2

Quantity Value Units Method Reference Comment
Deltar340.8 ± 2.1kcal/molG+TSMishima, Matsuoka, et al., 2004gas phase; Calc: keto form of acid more stable.; B
Deltar340.6 ± 2.1kcal/molG+TSTaft, Abboud, et al., 1988gas phase; B
Quantity Value Units Method Reference Comment
Deltar334.5 ± 2.0kcal/molIMREMishima, Matsuoka, et al., 2004gas phase; Calc: keto form of acid more stable.; B
Deltar334.3 ± 2.0kcal/molIMRETaft, Abboud, et al., 1988gas phase; B

3,3,3-Trimethoxypropionitrile + Water = Acetic acid, cyano-, methyl ester + 2Methyl Alcohol

By formula: C6H11NO3 + H2O = C4H5NO2 + 2CH4O

Quantity Value Units Method Reference Comment
Deltar-6.14 ± 0.35kcal/molEqkGuthrie and Cullimore, 1980liquid phase; ALS

Acetic acid, cyano-, methyl ester + Water = Acetic acid, cyano- + Methyl Alcohol

By formula: C4H5NO2 + H2O = C3H3NO2 + CH4O

Quantity Value Units Method Reference Comment
Deltar-13.0 ± 0.5kcal/molEqkGuthrie and Cullimore, 1980liquid phase; ALS

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
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
LL - Sharon G. Lias and Joel F. Liebman

Ionization energy determinations

IE (eV) Method Reference Comment
10.87 ± 0.05EIPignataro, Foffani, et al., 1966RDSH

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C2H3O2+10.40 ± 0.02C2H2NEIHolmes, Lossing, et al., 1993LL
C2H3O2+11.72 ± 0.03?EIBriggs and Shannon, 1969RDSH

De-protonation reactions

C4H4NO2- + Hydrogen cation = Acetic acid, cyano-, methyl ester

By formula: C4H4NO2- + H+ = C4H5NO2

Quantity Value Units Method Reference Comment
Deltar340.8 ± 2.1kcal/molG+TSMishima, Matsuoka, et al., 2004gas phase; Calc: keto form of acid more stable.; B
Deltar340.6 ± 2.1kcal/molG+TSTaft, Abboud, et al., 1988gas phase; B
Quantity Value Units Method Reference Comment
Deltar334.5 ± 2.0kcal/molIMREMishima, Matsuoka, et al., 2004gas phase; Calc: keto form of acid more stable.; B
Deltar334.3 ± 2.0kcal/molIMRETaft, Abboud, et al., 1988gas phase; B

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References, Notes

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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Mass 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 Japan AIST/NIMC Database- Spectrum MS-NW-5077
NIST MS number 228309

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Gas Chromatography

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

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryHP-5900.Jung, Wichmann, et al., 199925. m/0.20 mm/0.33 «mu»m, 50. C @ 3. min, 5. K/min; Tend: 180. C

References

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

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

Verevkin, Beckhaus, et al., 1995
Verevkin, S.P.; Beckhaus, H.-D.; Ruchardt, C., Geminale substituenteneffekte. Teil 6. Standardbildungsenthalpien von alkylsubstituierten-alkoxynitrilen und «alpha»-cyano-carbonsaureestern, Thermochim. Acta, 1995, 249, 1-11. [all data]

Guinchant, 1918
Guinchant, M.J., Etude sur la fonction acide dans les derives metheniques et methiniques, Ann. Chem., 1918, 10, 30-84. [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]

Dreisbach, 1955
Dreisbach, R.R., Physical Properties of Chemical Compounds, Advances in Chemistry Series No. 15, Am. Chem. Soc.: Washington, D. C., 1955. [all data]

Guthrie and Cullimore, 1980
Guthrie, J.P.; Cullimore, P.A., Effect of the acyl substituent on the equilibrium constant for hydration of esters, Can. J. Chem., 1980, 58, 1281-1294. [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]

Dykyj, 1971
Dykyj, J., Petrochemia, 1971, 11, 2, 27. [all data]

Mishima, Matsuoka, et al., 2004
Mishima, M.; Matsuoka, M.; Lei, Y.X.; Rappoport, Z., Gas-phase acidities of disubstituted methanes and of enols of carboxamides substituted by electron-withdrawing groups, J. Org. Chem., 2004, 69, 18, 5947-5965, https://doi.org/10.1021/jo040196b . [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]

Pignataro, Foffani, et al., 1966
Pignataro, S.; Foffani, A.; Innorta, G.; Distefano, G., Molecular structural effects on the ionization potentials for metasubstituted aromatic compounds and for compounds of the type X-CH2-R, Z. Physik. Chem. (Frankfurt), 1966, 49, 291. [all data]

Holmes, Lossing, et al., 1993
Holmes, J.L.; Lossing, F.P.; Mayer, P.M., The effects of methyl substitution on the structure and thermochemistry of the cyanomethyl radical and cation, Chem. Phys. Lett., 1993, 212, 134. [all data]

Briggs and Shannon, 1969
Briggs, P.R.; Shannon, T.W., The heat of formation of the methoxycarbonyl ion, J. Am. Chem. Soc., 1969, 91, 4307. [all data]

Jung, Wichmann, et al., 1999
Jung, A.; Wichmann, K.-H.; Kolb, M., VOC emission of polymeric packaging materials, LaborPraxis, 1999, 23, 9, 20-22. [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, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References