1-Naphthalenecarboxylic acid

Formula: C₁₁H₈O₂
Molecular weight: 172.1800
IUPAC Standard InChI: InChI=1S/C11H8O2/c12-11(13)10-7-3-5-8-4-1-2-6-9(8)10/h1-7H,(H,12,13)
IUPAC Standard InChIKey: LNETULKMXZVUST-UHFFFAOYSA-N
CAS Registry Number: 86-55-5
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
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Species with the same structure:
- Naphthoic acid
Other names: 1-Naphthoic acid; α-Naphthoic acid; 1-Carboxynaphthalene; 1-Naphthioic acid; Naphthalene-α-carboxylic acid; α-Naphthylcarboxylic acid
Information on this page:
Other data available:
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Gas phase thermochemistry data

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

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	-223.1	kJ/mol	Ccb	Colomina, Roux, et al., 1974

Condensed phase thermochemistry data

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

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_solid	-333.5 ± 1.0	kJ/mol	Ccb	Colomina, Roux, et al., 1974
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_solid	-5110.7 ± 5.1	kJ/mol	Ccb	Balcan, Arzik, et al., 1996	Corresponding Δ_fHº_solid = -361.2 kJ/mol (simple calculation by NIST; no Washburn corrections)
Δ_cH°_solid	-5150.9 ± 6.7	kJ/mol	Ccb	Holdiness, 1983	Corresponding Δ_fHº_solid = -321.0 kJ/mol (simple calculation by NIST; no Washburn corrections)
Δ_cH°_solid	-5138.41 ± 0.88	kJ/mol	Ccb	Colomina, Roux, et al., 1974	Corresponding Δ_fHº_solid = -333.5 kJ/mol (simple calculation by NIST; no Washburn corrections)
Δ_cH°_solid	-5138.43 ± 0.87	kJ/mol	Ccb	Sabbah and Gilbert, 1974	Corresponding Δ_fHº_solid = -333.50 kJ/mol (simple calculation by NIST; no Washburn corrections)

Phase change data

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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
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
T_boil	573.2	K	N/A	Aldrich Chemical Company Inc., 1990	BS
Quantity	Value	Units	Method	Reference	Comment
T_fus	434.15	K	N/A	Khetarpal, Lal, et al., 1979	Uncertainty assigned by TRC = 2. K; TRC
T_fus	433.9	K	N/A	Berliner and Winicov, 1959	Uncertainty assigned by TRC = 0.8 K; TRC
Quantity	Value	Units	Method	Reference	Comment
Δ_subH°	110.4	kJ/mol	N/A	Colomina, Roux, et al., 1974	DRB
Δ_subH°	113.64	kJ/mol	C	Sabbah and Gilbert, 1974	ALS
Δ_subH°	113.6	kJ/mol	C	Sabbah and Gilbert, 1974	AC

Enthalpy of vaporization

Δ_vapH (kJ/mol)	Temperature (K)	Method	Reference	Comment
97.2	472.	A	Stephenson and Malanowski, 1987	Based on data from 457. to 573. K.; 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
429. to 573.	8.27099	4590.279	-17.54	Stull, 1947	Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

Δ_subH (kJ/mol)	Temperature (K)	Method	Reference	Comment
110.4 ± 0.2	350.5	V	Colomina, Roux, et al., 1974	ALS
110.4 ± 0.2	355.	ME	Colomina, Roux, et al., 1974	Based on data from 340. to 360. K. See also Pedley and Rylance, 1977 and Stephenson and Malanowski, 1987.; AC

Enthalpy of fusion

Δ_fusH (kJ/mol)	Temperature (K)	Reference	Comment
19.89	435.2	Acree, 1991	AC

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:

References

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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]

Balcan, Arzik, et al., 1996
Balcan, M.; Arzik, S.; Altunata, T., The determination of the heats of combustion and the resonance energies of some substituted naphthalenes, Thermochim. Acta, 1996, 278, 49-56. [all data]

Holdiness, 1983
Holdiness, M.R., Heats of atomization and resonance energy of some ortho-substituted benzoic acids, Thermochim. Acta, 1983, 71, 257-263. [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]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

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]

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]

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

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Symbols used in this document:

T_boil	Boiling point
T_fus	Fusion (melting) point
Δ_cH°_solid	Enthalpy of combustion of solid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_solid	Enthalpy of formation of solid at standard conditions
Δ_fusH	Enthalpy of fusion
Δ_subH	Enthalpy of sublimation
Δ_subH°	Enthalpy of sublimation at standard conditions
Δ_vapH	Enthalpy of vaporization

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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