Propanedioic acid, dimethyl 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
Δfgas-176.35 ± 0.24kcal/molCcbVerevkin, Beckhaus, et al., 1992 
Δfgas-176.35 ± 0.24kcal/molCcbVerevkin, Dogan, et al., 1990 

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
Δfliquid-191.13 ± 0.15kcal/molCcbVerevkin, Beckhaus, et al., 1992ALS
Δfliquid-191.13 ± 0.15kcal/molCcbVerevkin, Dogan, et al., 1990ALS
Quantity Value Units Method Reference Comment
Δcliquid-552.38 ± 0.15kcal/molCcbVerevkin, Beckhaus, et al., 1992Corresponding Δfliquid = -191.14 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcliquid-552.38 ± 0.15kcal/molCcbVerevkin, Dogan, et al., 1990Corresponding Δfliquid = -191.14 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
Δcsolid-554.0kcal/molCcbVerkade, Coops, et al., 1926Heat of combustion at 15°C; Corresponding Δfsolid = -189.5 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
50.22298.15Verevkin, Beckhaus, et al., 1992DH

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
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.

Quantity Value Units Method Reference Comment
Tboil454.6KN/AWeast and Grasselli, 1989BS
Tboil454.6KN/ALecat, 1947Uncertainty assigned by TRC = 0.8 K; TRC
Tboil454.6KN/ALecat, 1926Uncertainty assigned by TRC = 0.5 K; TRC
Quantity Value Units Method Reference Comment
Tfus211.3KN/APalomaa and Mikkila, 1942Uncertainty assigned by TRC = 1. K; TRC
Quantity Value Units Method Reference Comment
Δvap13.7 ± 0.07kcal/molGSVerevkin, Kozlova, et al., 2006Based on data from 278. - 314. K.; AC
Δvap14.78 ± 0.19kcal/molVVerevkin, Beckhaus, et al., 1992ALS
Δvap14.78 ± 0.19kcal/molCVerevkin, Dogan, et al., 1990ALS
Δvap14.8kcal/molN/AVerevkin, Dogan, et al., 1990DRB
Quantity Value Units Method Reference Comment
Δsub26.70 ± 0.50kcal/molMERibeiro da Silva, Monte, et al., 2000AC

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
12.6 ± 0.05360.EBSteele, Chirico, et al., 2002Based on data from 351. - 460. K.; AC
11.8 ± 0.05400.EBSteele, Chirico, et al., 2002Based on data from 351. - 460. K.; AC
11.0 ± 0.07440.EBSteele, Chirico, et al., 2002Based on data from 351. - 460. K.; AC
14.8 ± 0.2293.GSVerevkin, Beckhaus, et al., 1992Based on data from 278. - 308. K.; AC
12.0497.EB,HGAskonas and Daubert, 1988Based on data from 374. - 620. K.; AC
12.8323.AStephenson and Malanowski, 1987Based on data from 308. - 454. 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
308. - 453.95.221612143.666-43.448Stull, 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

C5H7O4- + Hydrogen cation = Propanedioic acid, dimethyl ester

By formula: C5H7O4- + H+ = C5H8O4

Quantity Value Units Method Reference Comment
Δr348.0 ± 2.1kcal/molG+TSMishima, Matsuoka, et al., 2004gas phase; Calc: keto form of acid more stable.
Quantity Value Units Method Reference Comment
Δr341.3 ± 2.0kcal/molIMREMishima, Matsuoka, et al., 2004gas phase; Calc: keto form of acid more stable.

IR 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.

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

Gas Phase Spectrum

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IR spectrum
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Additional Data

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Owner NIST Standard Reference Data Program
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Sadtler Research Labs Under US-EPA Contract
State gas

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


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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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 T.A.BLAZER DU PONT, GIBBSTOWN, N.J., USA
NIST MS number 20883

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.


References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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., 1992
Verevkin, S.P.; Beckhaus, H.-D.; Ruchardt, C., Geminale substituenteneffekte Teil 5α. Standardbildungsenthalpien von alkylsubstituierten Malonsaure- und α-aminocarbonsaureestern, Thermochim. Acta, 1992, 197, 27-39. [all data]

Verevkin, Dogan, et al., 1990
Verevkin, S.; Dogan, B.; Beckhaus, H.D.; Ruechardt, C., Geminal substituent effects. 3. Synergistic destablization by geminal ester groups, Angew. Chem., 1990, 102, 693-695. [all data]

Verkade, Coops, et al., 1926
Verkade, P.E.; Coops, J.; Hartman, H., Calorimetric researches. XIII. Heats of combustion of successive terms of homologous series: Dimethyl esters of the oxalic acid series. A general survey of the oscillation phenomena, Recl. Trav. Chim. Pays-Bas, 1926, 45, 585-606. [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]

Lecat, 1947
Lecat, M., Orthobaric Azeotropes of Sulfides, Bull. Cl. Sci., Acad. R. Belg., 1947, 33, 160-82. [all data]

Lecat, 1926
Lecat, M., New binary azeotropes: 3rd list, Ann. Soc. Sci. Bruxelles, Ser. B, 1926, 45, 284-94. [all data]

Palomaa and Mikkila, 1942
Palomaa, M.H.; Mikkila, I., Etherlike Compounds XXVII Turbid Phases in Compounds with Reactivity Minimums, Chem. Ber., 1942, 75B, 1659-67. [all data]

Verevkin, Kozlova, et al., 2006
Verevkin, Sergey P.; Kozlova, Svetlana A.; Emel'yanenko, Vladimir N.; Nikitin, Eugene D.; Popov, Alexander P.; Krasnykh, Eugen L., Vapor Pressures, Enthalpies of Vaporization, and Critical Parameters of a Series of Linear Aliphatic Dimethyl Esters of Dicarboxylic Acids, J. Chem. Eng. Data, 2006, 51, 5, 1896-1905, https://doi.org/10.1021/je0602418 . [all data]

Ribeiro da Silva, Monte, et al., 2000
Ribeiro da Silva, Manuel A.V.; Monte, Manuel J.S.; Ribeiro, José R., Standard Enthalpies, Entropies, and Gibbs Functions of Sublimation of Four Alkyl-Substituted Malonic Acids, J. Chem. Eng. Data, 2000, 45, 5, 756-759, https://doi.org/10.1021/je000090n . [all data]

Steele, Chirico, et al., 2002
Steele, W.V.; Chirico, R.D.; Cowell, A.B.; Knipmeyer, S.E.; Nguyen, A., Thermodynamic Properties and Ideal-Gas Enthalpies of Formation for 1,4-Diisopropylbenzene, 1,2,4,5-Tetraisopropylbenzene, Cyclohexanone Oxime, Dimethyl Malonate, Glutaric Acid, and Pimelic Acid, J. Chem. Eng. Data, 2002, 47, 4, 725-739, https://doi.org/10.1021/je010088b . [all data]

Askonas and Daubert, 1988
Askonas, Charles F.; Daubert, Thomas E., Vapor pressure determination of eight oxygenated compounds, J. Chem. Eng. Data, 1988, 33, 3, 225-229, https://doi.org/10.1021/je00053a001 . [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]

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]


Notes

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