Hexanedioic 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 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
Δfsolid-244.101kcal/molCcbContineanu, Corlateanu, et al., 1980ALS
Δfsolid-238.58 ± 0.10kcal/molCcbBabinkov, Nistratov, et al., 1979ALS
Quantity Value Units Method Reference Comment
Δcsolid-661.7 ± 1.4kcal/molCcbContineanu, Corlateanu, et al., 1980Corresponding Δfsolid = -244.152 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcsolid-667.30 ± 0.10kcal/molCcbBabinkov, Nistratov, et al., 1979Corresponding Δfsolid = -238.58 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcsolid-668.23 ± 0.18kcal/molCcrSunner, 1946Corresponding Δfsolid = -237.65 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcsolid-669.80 ± 0.33kcal/molCcbVerkade, Hartman, et al., 1926Reanalyzed by Cox and Pilcher, 1970, Original value = -668.9 kcal/mol; See Verkade, Hartman, et al., 1924; Corresponding Δfsolid = -236.08 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS

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
DH - Eugene S. Domalski and Elizabeth D. Hearing
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

Quantity Value Units Method Reference Comment
Tfus425. ± 4.KAVGN/AAverage of 12 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple424.7KN/ABabinkov, Nistratov, et al., 1979, 2Uncertainty assigned by TRC = 0.3 K; TRC
Quantity Value Units Method Reference Comment
Δvap25.14kcal/molCGCRoux, Temprado, et al., 2005Based on data from 424. to 503. K.; AC
Quantity Value Units Method Reference Comment
Δsub31.93 ± 0.31kcal/molMERibeiro da Silva, Monte, et al., 1999See also Davies and Thomas, 1960.; AC
Δsub30.9 ± 0.3kcal/molVDavies and Thomas, 1960ALS

Reduced pressure boiling point

Tboil (K) Pressure (atm) Reference Comment
538.20.132Weast and Grasselli, 1989BS

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
22.0447.AStephenson and Malanowski, 1987Based on data from 432. to 611. 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
432.7 to 610.75.467352813.066-95.951Stull, 1947Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

ΔsubH (kcal/mol) Temperature (K) Method Reference Comment
29.8 ± 4.8353. to 373.METaulelle, Sitja, et al., 2009AC
34.7 ± 1.328. to 368.TPDCappa, Lovejoy, et al., 2007AC
34.94285. to 307.TPTDChattopadhyay and Ziemann, 2005AC
33.5295. to 318.TPTDChattopadhyay, Tobias, et al., 2001Values based on TPTD method are not consistent with values determined by other experimental methods; AC
30.90 ± 0.60383.MENitta, Seki, et al., 1950Based on data from 359. to 406. K. See also Jones, 1960 and Cox and Pilcher, 1970, 2.; AC

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Reference Comment
8.3298425.5Cingolani and Berchiesi, 1974DH
8.05419.Roux, Temprado, et al., 2005AC
8.329426.4Acree, 1991AC

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
19.58425.5Cingolani 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

C6H9O4- + Hydrogen cation = Hexanedioic acid

By formula: C6H9O4- + H+ = C6H10O4

Quantity Value Units Method Reference Comment
Δr325.1 ± 2.0kcal/molCIDCKumar, Prabhakar, et al., 2005gas phase
Quantity Value Units Method Reference Comment
Δr321.1 ± 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.
1.8×10+711000.XN/A 

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

C6H9O4- + Hydrogen cation = Hexanedioic acid

By formula: C6H9O4- + H+ = C6H10O4

Quantity Value Units Method Reference Comment
Δr325.1 ± 2.0kcal/molCIDCKumar, Prabhakar, et al., 2005gas phase
Quantity Value Units Method Reference Comment
Δr321.1 ± 2.0kcal/molCIDCKumar, Prabhakar, et al., 2005gas phase

IR Spectrum

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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- 242
NIST MS number 228440

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Gas Chromatography

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, 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

Van Den Dool and Kratz RI, non-polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryVF-5MS1372.4Tret'yakov, 200730. m/0.25 mm/0.25 μm, He; Program: Multi-step temperature program; T(initial)=60C; T(final)=270C

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryCarbowax 20M2137.Editorial paper, 2005Program: not specified

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), Gas Chromatography, Notes

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

Contineanu, Corlateanu, et al., 1980
Contineanu, I.; Corlateanu, E.; Hersocovici, J.; Marchidan, D.I., Combustion and formation enthalpies of 1,6-hexanediol and adipic acid, Rev. Chim. (Bucharest), 1980, 31, 763-764. [all data]

Babinkov, Nistratov, et al., 1979
Babinkov, A.G.; Nistratov, V.P.; Larina, V.N.; Shvetsova, K.G.; Sapozhnikov, V.N.; Zhilitskaya, O.M., Thermodynamic properties of adipic acid, Termodin. Org. Soedin., 1979, 28-33. [all data]

Sunner, 1946
Sunner, S., Determination of combustion heats of organo-sulphur compounds, Svensk. Kim. Tidr., 1946, 58, 71-81. [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]

Babinkov, Nistratov, et al., 1979, 2
Babinkov, A.G.; Nistratov, V.P.; Larina, V.N.; Shvetsova, K.G.; Sapozhnikov, V.N.; Zhilitskaya, O.M., Thermodynamic properties of aclipic acid., Termodin. Org. Soedin., 1979, No. 8, 28. [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]

Davies and Thomas, 1960
Davies, M.; Thomas, G.H., The lattice energies, infra-red spectra, and possible cyclization of some dicarboxylic acids, Trans. Faraday Soc., 1960, 56, 185. [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]

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]

Taulelle, Sitja, et al., 2009
Taulelle, Pascal; Sitja, Georges; Pepe, Gerard; Garcia, Eric; Hoff, Christian; Veesler, Stephane, Measuring Enthalpy of Sublimation for Active Pharmaceutical Ingredients: Validate Crystal Energy and Predict Crystal Habit, Crystal Growth & Design, 2009, 9, 11, 4706-4709, https://doi.org/10.1021/cg900567z . [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]

Chattopadhyay, Tobias, et al., 2001
Chattopadhyay, Sulekha; Tobias, Herbert J.; Ziemann, Paul J., A Method for Measuring Vapor Pressures of Low-Volatility Organic Aerosol Compounds Using a Thermal Desorption Particle Beam Mass Spectrometer, Anal. Chem., 2001, 73, 16, 3797-3803, https://doi.org/10.1021/ac010304j . [all data]

Nitta, Seki, et al., 1950
Nitta, I.; Seki, S.; Momotani, M.; Suzuki, K.; Nakagawa, S., On the phase transition in pentaerythritol (II)., Proc. Jpn. Acad., 1950, 26, 11. [all data]

Jones, 1960
Jones, A.H., Sublimation Pressure Data for Organic Compounds., J. Chem. Eng. Data, 1960, 5, 2, 196-200, https://doi.org/10.1021/je60006a019 . [all data]

Cox and Pilcher, 1970, 2
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [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]

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]

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]

Tret'yakov, 2007
Tret'yakov, K.V., Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2007. [all data]

Editorial paper, 2005
Editorial paper, Solid Phase Microextraction (SPME) Application Guide, The Reporter Europe (Supelco), 2005, 16, 5, 12-12. [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), Gas Chromatography, References