2-Naphthalenecarboxylic acid
- Formula: C11H8O2
- Molecular weight: 172.1800
- IUPAC Standard InChI: InChI=1S/C11H8O2/c12-11(13)10-6-5-8-3-1-2-4-9(8)7-10/h1-7H,(H,12,13)
- IUPAC Standard InChIKey: UOBYKYZJUGYBDK-UHFFFAOYSA-N
- CAS Registry Number: 93-09-4
- 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: 2-Naphthoic acid; β-Naphthoic acid; Isonaphthoic acid; 2-Carboxynaphthalene; 2-Maythic acid; 2-Naphthioic acid; Naphthalene-β-carboxylic acid; NSC 59901; 2-Naphthylcarboxylic acid
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Phase change data
Go To: Top, 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tfus | 458.15 | K | N/A | Khetarpal, Lal, et al., 1979 | Uncertainty assigned by TRC = 2. K; TRC |
| Tfus | 457.2 | K | N/A | Berliner and Winicov, 1959 | Uncertainty assigned by TRC = 1.5 K; TRC |
| Tfus | 457.56 | K | N/A | Witschonke, 1954 | Uncertainty assigned by TRC = 0.35 K; TRC |
| Tfus | 458.75 | K | N/A | Witschonke, 1954 | Uncertainty assigned by TRC = 0.25 K; TRC |
| Tfus | 458. | K | N/A | Bailey and Golden, 1953 | Uncertainty assigned by TRC = 3. K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔsubH° | 27.15 | kcal/mol | N/A | Colomina, Roux, et al., 1974 | DRB |
| ΔsubH° | 28.009 | kcal/mol | C | Sabbah and Gilbert, 1974 | ALS |
| ΔsubH° | 28.01 | kcal/mol | C | Sabbah and Gilbert, 1974 | AC |
Enthalpy of vaporization
| ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 23.6 | 478. | A | Stephenson and Malanowski, 1987 | Based on data from 463. - 582. K.; AC |
Enthalpy of sublimation
| ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 27.15 ± 0.19 | 355.6 | V | Colomina, Roux, et al., 1974 | ALS |
| 27.2 ± 0.2 | 365. | ME | Colomina, Roux, et al., 1974 | Based on data from 347. - 363. K. See also Pedley and Rylance, 1977 and Stephenson and Malanowski, 1987.; AC |
Enthalpy of fusion
| ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 5.626 | 460.2 | Acree, 1991 | AC |
References
Go To: Top, Phase change data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Khetarpal, Lal, et al., 1979
Khetarpal, S.C.; Lal, K.; Bhatnagar, H.L.,
Thermodynamic Studies on Melting of Some α- and β-Derivitives of Naphthalene,
Aust. J. Chem., 1979, 32, 49. [all data]
Berliner and Winicov, 1959
Berliner, E.; Winicov, E.H.,
Dissociation Constants of Nitronaphtoic Acid,
J. Am. Chem. Soc., 1959, 81, 1630-5. [all data]
Witschonke, 1954
Witschonke, C.R.,
Freezing point and purity data for some organic compounds,
Anal. Chem., 1954, 26, 562-4. [all data]
Bailey and Golden, 1953
Bailey, W.J.; Golden, H.R.,
Cyclic Dienes I. 1,2-Dimethylenecyclohexane,
J. Am. Chem. Soc., 1953, 75, 4780-2. [all data]
Colomina, Roux, et al., 1974
Colomina, M.; Roux, M.V.; Turrion, C.,
Thermochemical properties of naphthalene compounds. I. Enthalpies of combustion and formation of the 1- and 2-naphthoic acids,
J. Chem. Thermodyn., 1974, 6, 149-155. [all data]
Sabbah and Gilbert, 1974
Sabbah, R.; Gilbert, E.M.,
Determination de L'energie de conjugaison des acides naphtoiques,
Thermochim. Acta, 1974, 10, 345-351. [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]
Pedley and Rylance, 1977
Pedley, J.B.; Rylance, J.,
, Computer Analysed Thermochemical Data: Organic and Organometallic Compounds, University of Sussex, Brighton, 1977. [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]
Notes
Go To: Top, Phase change data, References
- Symbols used in this document:
Tfus Fusion (melting) point ΔfusH Enthalpy of fusion ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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