Pentanedioic acid
- Formula: C5H8O4
- Molecular weight: 132.1146
- IUPAC Standard InChIKey: JFCQEDHGNNZCLN-UHFFFAOYSA-N
- CAS Registry Number: 110-94-1
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: Glutaric acid; 1,3-Propanedicarboxylic acid; 1,5-Pentanedioic acid; Pentandioic acid
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Condensed phase thermochemistry data
Go To: Top, Phase change data, Reaction thermochemistry data, 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 |
---|---|---|---|---|---|
ΔfH°solid | -960.5 ± 1.1 | kJ/mol | Ccb | El-Sayed, 1993 | |
ΔfH°solid | -960.0 ± 1.2 | kJ/mol | Ccb | Wilhoit and Shiao, 1964 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -2150.35 ± 0.75 | kJ/mol | Ccb | El-Sayed, 1993 | Corresponding ΔfHºsolid = -960.52 kJ/mol (simple calculation by NIST; no Washburn corrections) |
ΔcH°solid | -2150.9 ± 1.2 | kJ/mol | Ccb | Wilhoit and Shiao, 1964 | Corresponding ΔfHºsolid = -959.98 kJ/mol (simple calculation by NIST; no Washburn corrections) |
ΔcH°solid | -2151.6 ± 0.50 | kJ/mol | Ccb | Verkade, Hartman, et al., 1926 | Reanalyzed by Cox and Pilcher, 1970, Original value = -2154. kJ/mol; See Verkade, Hartman, et al., 1924; Corresponding ΔfHºsolid = -959.31 kJ/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 |
---|---|---|---|---|---|
Tfus | 370.7 ± 0.9 | K | AVG | N/A | Average of 9 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 101.6 | kJ/mol | GS | Roux, Temprado, et al., 2005 | Based on data from 424. to 503. K.; AC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 119.8 ± 1.2 | kJ/mol | ME | Ribeiro da Silva, Monte, et al., 1999 | Based on data from 348. to 363. K.; AC |
Reduced pressure boiling point
Tboil (K) | Pressure (bar) | Reference | Comment |
---|---|---|---|
473.2 | 0.027 | Aldrich Chemical Company Inc., 1990 | BS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
98.1 | 443. | A | Stephenson and Malanowski, 1987 | Based on data from 428. to 576. K. See also Stull, 1947.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
428.7 to 576. | 7.67973 | 4140.732 | -36.41 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
134. ± 4. | 313. to 349. | TPD | Cappa, Lovejoy, et al., 2007 | AC |
132.3 | 275. to 294. | TPTD | Chattopadhyay and Ziemann, 2005 | Values based on TPTD method are not consistent with values determined by other experimental methods; AC |
117.0 ± 1.2 | 356. | ME | Ribeiro da Silva, Monte, et al., 1999 | Based on data from 348. to 363. K.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
20.7 | 370.9 | DSC | Good and Rodriguez-Hornedo, 2009 | AC |
21.3 | 372.3 | DSC | Ha, Hamilton, et al., 2009 | AC |
18.8 | 363.9 | DSC | Roux, Temprado, et al., 2005 | AC |
23. | 371. | N/A | Steele, Chirico, et al., 2002 | AC |
20.9 | 371. | N/A | Acree, 1991 | AC |
Enthalpy of phase transition
ΔHtrs (kJ/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
2.400 | 338.0 | crystaline, II | crystaline, I | Petropavlov, Tsygankova, et al., 1988 | DH |
2.464 | 348.5 | crystaline, II | crystaline, I | Cingolani and Berchiesi, 1974 | DH |
20.899 | 371.0 | crystaline, I | liquid | Cingolani and Berchiesi, 1974 | DH |
Entropy of phase transition
ΔStrs (J/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
7.1 | 338.0 | crystaline, II | crystaline, I | Petropavlov, Tsygankova, et al., 1988 | DH |
7.07 | 348.5 | crystaline, II | crystaline, I | Cingolani and Berchiesi, 1974 | DH |
56.32 | 371.0 | crystaline, I | liquid | Cingolani and Berchiesi, 1974 | DH |
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- + =
By formula: C5H7O4- + H+ = C5H8O4
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1367. ± 8.4 | kJ/mol | CIDC | Kumar, Prabhakar, et al., 2005 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1338. ± 8.4 | kJ/mol | CIDC | Kumar, Prabhakar, et al., 2005 | gas phase |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, 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, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔfusH Enthalpy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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