Home Symbol which looks like a small house Up Solid circle with an upward pointer in it

Propanedioic acid, dimethyl ester

Data at NIST subscription sites:

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.


Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafgas-737.8 ± 1.0kJ/molCcbVerevkin, Beckhaus, et al., 1992 
Deltafgas-737.8 ± 1.0kJ/molCcbVerevkin, Dogan, et al., 1990 

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry 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 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
Deltafliquid-799.69 ± 0.63kJ/molCcbVerevkin, Beckhaus, et al., 1992ALS
Deltafliquid-799.69 ± 0.63kJ/molCcbVerevkin, Dogan, et al., 1990ALS
Quantity Value Units Method Reference Comment
Deltacliquid-2311.2 ± 0.63kJ/molCcbVerevkin, Beckhaus, et al., 1992Corresponding «DELTA»fliquid = -799.73 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacliquid-2311.2 ± 0.63kJ/molCcbVerevkin, Dogan, et al., 1990Corresponding «DELTA»fliquid = -799.73 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
Deltacsolid-2318.kJ/molCcbVerkade, Coops, et al., 1926Heat of combustion at 15°C; Corresponding «DELTA»fsolid = -792.9 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
210.1298.15Verevkin, Beckhaus, et al., 1992DH

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry 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 as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Kenneth Kroenlein 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
Deltavap57.5 ± 0.3kJ/molGSVerevkin, Kozlova, et al., 2006Based on data from 278. - 314. K.; AC
Deltavap61.84 ± 0.79kJ/molVVerevkin, Beckhaus, et al., 1992ALS
Deltavap61.84 ± 0.79kJ/molCVerevkin, Dogan, et al., 1990ALS
Deltavap61.9kJ/molN/AVerevkin, Dogan, et al., 1990DRB
Quantity Value Units Method Reference Comment
Deltasub111.7 ± 2.1kJ/molMERibeiro da Silva, Monte, et al., 2000AC

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
52.9 ± 0.2360.EBSteele, Chirico, et al., 2002Based on data from 351. - 460. K.; AC
49.5 ± 0.2400.EBSteele, Chirico, et al., 2002Based on data from 351. - 460. K.; AC
46.1 ± 0.3440.EBSteele, Chirico, et al., 2002Based on data from 351. - 460. K.; AC
61.8 ± 0.8293.GSVerevkin, Beckhaus, et al., 1992Based on data from 278. - 308. K.; AC
50.0497.EB,HGAskonas and Daubert, 1988Based on data from 374. - 620. K.; AC
53.7323.AStephenson and Malanowski, 1987Based on data from 308. - 454. K.; AC

Antoine Equation Parameters

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

View plot Requires a JavaScript / HTML 5 canvas capable browser.

Temperature (K) A B C Reference Comment
308. - 453.95.227322143.666-43.448Stull, 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

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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: 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
Deltar1456. ± 8.8kJ/molG+TSMishima, Matsuoka, et al., 2004gas phase; Calc: keto form of acid more stable.
Quantity Value Units Method Reference Comment
Deltar1428. ± 8.4kJ/molIMREMishima, Matsuoka, et al., 2004gas phase; Calc: keto form of acid more stable.

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, 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

Gas Phase Spectrum

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

IR spectrum
For Zoom
1.) Enter the desired X axis range (e.g., 100, 200)
2.) Check here for automatic Y scaling
3.) Press here to zoom

Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.

Additional Data

View image of digitized spectrum (can be printed in landscape orientation).

View spectrum image in SVG format.

Download spectrum in JCAMP-DX format.

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)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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

Spectrum

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

Mass spectrum
For Zoom
1.) Enter the desired X axis range (e.g., 100, 200)
2.) Check here for automatic Y scaling
3.) Press here to zoom

Additional Data

View image of digitized spectrum (can be printed in landscape orientation).

View spectrum image in SVG format.

Download spectrum in JCAMP-DX format.

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 5«alpha». Standardbildungsenthalpien von alkylsubstituierten Malonsaure- und «alpha»-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