Pentanedioic acid

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

Quantity Value Units Method Reference Comment
Δfsolid-229.57 ± 0.26kcal/molCcbEl-Sayed, 1993 
Δfsolid-229.44 ± 0.29kcal/molCcbWilhoit and Shiao, 1964 
Quantity Value Units Method Reference Comment
Δcsolid-513.95 ± 0.18kcal/molCcbEl-Sayed, 1993Corresponding Δfsolid = -229.57 kcal/mol (simple calculation by NIST; no Washburn corrections)
Δcsolid-514.08 ± 0.28kcal/molCcbWilhoit and Shiao, 1964Corresponding Δfsolid = -229.44 kcal/mol (simple calculation by NIST; no Washburn corrections)
Δcsolid-514.24 ± 0.12kcal/molCcbVerkade, Hartman, et al., 1926Reanalyzed by Cox and Pilcher, 1970, Original value = -514.9 kcal/mol; See Verkade, Hartman, et al., 1924; Corresponding Δfsolid = -229.28 kcal/mol (simple calculation by NIST; no Washburn corrections)

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
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tfus370.7 ± 0.9KAVGN/AAverage of 9 values; Individual data points
Quantity Value Units Method Reference Comment
Δvap24.28kcal/molGSRoux, Temprado, et al., 2005Based on data from 424. to 503. K.; AC
Quantity Value Units Method Reference Comment
Δsub28.63 ± 0.29kcal/molMERibeiro da Silva, Monte, et al., 1999Based on data from 348. to 363. K.; AC

Reduced pressure boiling point

Tboil (K) Pressure (atm) Reference Comment
473.20.026Aldrich Chemical Company Inc., 1990BS

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
23.4443.AStephenson and Malanowski, 1987Based on data from 428. to 576. K. See also Stull, 1947.; 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
428.7 to 576.7.674024140.732-36.41Stull, 1947Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

ΔsubH (kcal/mol) Temperature (K) Method Reference Comment
32.0 ± 1.313. to 349.TPDCappa, Lovejoy, et al., 2007AC
31.62275. to 294.TPTDChattopadhyay and Ziemann, 2005Values based on TPTD method are not consistent with values determined by other experimental methods; AC
27.96 ± 0.29356.MERibeiro da Silva, Monte, et al., 1999Based on data from 348. to 363. K.; AC

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Method Reference Comment
4.95370.9DSCGood and Rodriguez-Hornedo, 2009AC
5.09372.3DSCHa, Hamilton, et al., 2009AC
4.49363.9DSCRoux, Temprado, et al., 2005AC
5.5371.N/ASteele, Chirico, et al., 2002AC
5.00371.N/AAcree, 1991AC

Enthalpy of phase transition

ΔHtrs (kcal/mol) Temperature (K) Initial Phase Final Phase Reference Comment
0.5736338.0crystaline, IIcrystaline, IPetropavlov, Tsygankova, et al., 1988DH
0.5889348.5crystaline, IIcrystaline, ICingolani and Berchiesi, 1974DH
4.9950371.0crystaline, IliquidCingolani and Berchiesi, 1974DH

Entropy of phase transition

ΔStrs (cal/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
1.7338.0crystaline, IIcrystaline, IPetropavlov, Tsygankova, et al., 1988DH
1.69348.5crystaline, IIcrystaline, ICingolani and Berchiesi, 1974DH
13.46371.0crystaline, IliquidCingolani and Berchiesi, 1974DH

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 = Pentanedioic acid

By formula: C5H7O4- + H+ = C5H8O4

Quantity Value Units Method Reference Comment
Δr326.7 ± 2.0kcal/molCIDCKumar, Prabhakar, et al., 2005gas phase
Quantity Value Units Method Reference Comment
Δr319.7 ± 2.0kcal/molCIDCKumar, Prabhakar, et al., 2005gas phase

Henry's Law 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: Rolf Sander

Henry's Law constant (water solution)

kH(T) = H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(kH))/d(1/T) = Temperature dependence constant (K)

H (mol/(kg*bar)) d(ln(kH))/d(1/T) (K) Method Reference Comment
2.0×10+8 EN/AValue obtained by missing citation using the group contribution method.

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 by: John E. Bartmess

De-protonation reactions

C5H7O4- + Hydrogen cation = Pentanedioic acid

By formula: C5H7O4- + H+ = C5H8O4

Quantity Value Units Method Reference Comment
Δr326.7 ± 2.0kcal/molCIDCKumar, Prabhakar, et al., 2005gas phase
Quantity Value Units Method Reference Comment
Δr319.7 ± 2.0kcal/molCIDCKumar, Prabhakar, et al., 2005gas phase

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

Data compiled by: Timothy J. Johnson, Tanya L. Myers, Yin-Fong Su, Russell G. Tonkyn, Molly Rose K. Kelly-Gorham, and Tyler O. Danby


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 NIST Mass Spectrometry Data Center, 1998.
NIST MS number 290975

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References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics 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.

El-Sayed, 1993
El-Sayed, N.I., The enthalpy of combustion and formation of hydantoin, Asian J. Chem., 1993, 5, 199-207. [all data]

Wilhoit and Shiao, 1964
Wilhoit, R.C.; Shiao, D., Thermochemistry of biologically important compounds. Heats of combustion of solid organic acids., J. Chem. Eng. Data, 1964, 9, 595-599. [all data]

Verkade, Hartman, et al., 1926
Verkade, P.E.; Hartman, H.; Coops, J., Calorimetric researches. X. Heats of combustion of successive terms of homologous series: dicarboxylic acids of the oxalic acid series, Rec. Trav. Chim. Pays/Bas, 1926, 45, 373-393. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Verkade, Hartman, et al., 1924
Verkade, P.E.; Hartman, H.; Coops, J., Jr., Chemistry - The molecular heat of combustion of successive terms of homologous series, Kom. Med. Akad. Ueknschap. Proc., 1924, 27, 859-866. [all data]

Roux, Temprado, et al., 2005
Roux, Maria Victoria; Temprado, Manuel; Chickos, James S., Vaporization, fusion and sublimation enthalpies of the dicarboxylic acids from C4 to C14 and C16, The Journal of Chemical Thermodynamics, 2005, 37, 9, 941-953, https://doi.org/10.1016/j.jct.2004.12.011 . [all data]

Ribeiro da Silva, Monte, et al., 1999
Ribeiro da Silva, Manuel A.V.; Monte, Manuel J.S.; Ribeiro, José R., Vapour pressures and the enthalpies and entropies of sublimation of five dicarboxylic acids, The Journal of Chemical Thermodynamics, 1999, 31, 8, 1093-1107, https://doi.org/10.1006/jcht.1999.0522 . [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]

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]

Cappa, Lovejoy, et al., 2007
Cappa, Christopher D.; Lovejoy, Edward R.; Ravishankara, A.R., Determination of Evaporation Rates and Vapor Pressures of Very Low Volatility Compounds: A Study of the C 4 -C 10 and C 12 Dicarboxylic Acids, J. Phys. Chem. A, 2007, 111, 16, 3099-3109, https://doi.org/10.1021/jp068686q . [all data]

Chattopadhyay and Ziemann, 2005
Chattopadhyay, Sulekha; Ziemann, Paul J., Vapor Pressures of Substituted and Unsubstituted Monocarboxylic and Dicarboxylic Acids Measured Using an Improved Thermal Desorption Particle Beam Mass Spectrometry Method, Aerosol Science and Technology, 2005, 39, 11, 1085-1100, https://doi.org/10.1080/02786820500421547 . [all data]

Good and Rodriguez-Hornedo, 2009
Good, David J.; Rodriguez-Hornedo, Nair, Solubility Advantage of Pharmaceutical Cocrystals, Crystal Growth & Design, 2009, 9, 5, 2252-2264, https://doi.org/10.1021/cg801039j . [all data]

Ha, Hamilton, et al., 2009
Ha, Jeong-Myeong; Hamilton, Benjamin D.; Hillmyer, Marc A.; Ward, Michael D., Phase Behavior and Polymorphism of Organic Crystals Confined within Nanoscale Chambers, Crystal Growth & Design, 2009, 9, 11, 4766-4777, https://doi.org/10.1021/cg9006185 . [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]

Acree, 1991
Acree, William E., Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation, Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H . [all data]

Petropavlov, Tsygankova, et al., 1988
Petropavlov, N.N.; Tsygankova, I.G.; Teslenko, L.A., Microcalorimetric investigation of polymorphic transitions in organic crystals, Sov. Phys. Crystallogr., 1988, 33(6), 853-855. [all data]

Cingolani and Berchiesi, 1974
Cingolani, A.; Berchiesi, G., Thermodynamic properties of organic compounds. 1. A DSC study of phase transitions in aliphatic dicarboxylic acids, J. Therm. Anal., 1974, 6, 87-90. [all data]

Kumar, Prabhakar, et al., 2005
Kumar, M.R.; Prabhakar, S.; Nagaveni, V.; Vairamani, M., Estimation of gas-phase acidities of a series of dicarboxylic acids by the kinetic method, Rapid Commun. Mass Spectrom., 2005, 19, 8, 1053-1057, https://doi.org/10.1002/rcm.1888 . [all data]


Notes

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