Azelaic acid
- Formula: C9H16O4
- Molecular weight: 188.2209
- IUPAC Standard InChI: InChI=1S/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13)
- IUPAC Standard InChIKey: BDJRBEYXGGNYIS-UHFFFAOYSA-N
- CAS Registry Number: 123-99-9
- 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: Nonanedioic acid; Anchoic acid; Emerox 1144; Lepargylic acid; 1,7-Heptanedicarboxylic acid; Heptanedicarboxylic acid; Azelainic acid; Azelaic acid, technical grade; Emerox 1110; 1,9-Nonanedioic acid; 1,7-Dicarboxyheptane; n-Nonanedioic acid; Emery's L-110; Skinoren; ZK-62498; Finacea; NSC 19493
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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 |
|---|---|---|---|---|---|
| ΔfH°solid | -1054.3 ± 0.9 | kJ/mol | Ccb | Vasil'ev, Borodin, et al., 1991 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -4773.9 ± 1.9 | kJ/mol | Ccb | Vasil'ev, Borodin, et al., 1991 | Corresponding ΔfHºsolid = -1054.3 kJ/mol (simple calculation by NIST; no Washburn corrections) |
| ΔcH°solid | -4775.6 | kJ/mol | Ccr | Sunner, 1946 | Corresponding ΔfHºsolid = -1053. kJ/mol (simple calculation by NIST; no Washburn corrections) |
| ΔcH°solid | -4773.9 ± 1.9 | kJ/mol | Ccb | Verkade, Hartman, et al., 1926 | Reanalyzed by Cox and Pilcher, 1970, Original value = -4776.9 kJ/mol; See Verkade, Hartman, et al., 1924; Corresponding ΔfHºsolid = -1054.3 kJ/mol (simple calculation by NIST; no Washburn corrections) |
Reaction thermochemistry data
Go To: Top, Condensed phase 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: 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
C9H15O4- + =
By formula: C9H15O4- + H+ = C9H16O4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1354. ± 8.4 | kJ/mol | CIDC | Kumar, Prabhakar, et al., 2005 | gas phase |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1349. ± 8.4 | kJ/mol | CIDC | Kumar, Prabhakar, et al., 2005 | gas phase |
References
Go To: Top, Condensed phase thermochemistry 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.
Vasil'ev, Borodin, et al., 1991
Vasil'ev, V.P.; Borodin, V.A.; Kopnyshev, S.B.,
Calculation of the standard enthalpies of combustion and of formation of crystalline organic acids and complexones from the energy contributions of atomic groups,
Russ. J. Phys. Chem. (Engl. Transl.), 1991, 65, 29-32. [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]
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, Reaction thermochemistry data, References
- Symbols used in this document:
ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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