2-Naphthalenol
- Formula: C10H8O
- Molecular weight: 144.1699
- IUPAC Standard InChIKey: JWAZRIHNYRIHIV-UHFFFAOYSA-N
- CAS Registry Number: 135-19-3
- 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: β-Naphthol; 2-Naphthol; β-Hydroxynaphthalene; Azogen Developer A; Betanaphthol; C.I. Azoic Coupling Component 1; C.I. Developer 5; C.I. 37500; Developer A; Developer AMS; Developer BN; Isonaphthol; Naphthol B; 2-Hydroxynaphthalene; β-Monoxynaphthalene; β-Naftol; β-Naftolo; β-Naphthyl alcohol; β-Naphthyl hydroxide; β-Naphtol; β-Napthol; Naphthol, β; 2-Naftol; 2-Naftolo; 2-Naphtol; Antioxygene BN; NSC 2044
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Gas phase thermochemistry data
Go To: Top, Phase change data, 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -29.9 ± 1.7 | kJ/mol | Ccb | Ribeiro Da Silva, Ribeiro Da Silva, et al., 1988 | Hs=94.2±0.5 kJ/mol; Colomina, Roux, et al., 1974; ALS |
ΔfH°gas | -30.0 ± 1.1 | kJ/mol | Ccb | Colomina, Roux, et al., 1974, 2 | ALS |
ΔfH°gas | -13.8 | kJ/mol | N/A | Pushin, 1954 | Value computed using ΔfHsolid° value of -108.0 kj/mol from Pushin, 1954 and ΔsubH° value of 94.2 kj/mol from Ribeiro Da Silva, Ribeiro Da Silva, et al., 1988.; DRB |
Quantity | Value | Units | Method | Reference | Comment |
S°gas | 366.6 ± 3.9 | J/mol*K | N/A | Kudchadker S.A., 1978 | GT |
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
36.84 | 50. | Kudchadker S.A., 1978 | GT |
51.65 | 100. | ||
72.43 | 150. | ||
96.49 | 200. | ||
134.64 | 273.15 | ||
147.82 | 298.15 | ||
148.79 | 300. | ||
198.20 | 400. | ||
239.23 | 500. | ||
271.78 | 600. | ||
297.61 | 700. | ||
318.45 | 800. | ||
335.56 | 900. | ||
349.82 | 1000. | ||
361.83 | 1100. | ||
372.02 | 1200. | ||
380.74 | 1300. | ||
388.22 | 1400. | ||
394.68 | 1500. |
Phase change data
Go To: Top, Gas phase thermochemistry data, 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 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 558.7 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 559. | K | N/A | Mantyukov, Loginova, et al., 1974 | Uncertainty assigned by TRC = 0.4 K; TRC |
Tboil | 568. | K | N/A | May, Berliner, et al., 1927 | Uncertainty assigned by TRC = 0.3 K; probably calculated from vapor pressure equation; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 394. ± 3. | K | AVG | N/A | Average of 9 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 393.8 | K | N/A | Andrews, Lynn, et al., 1926 | Uncertainty assigned by TRC = 1.25 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 76.2 | kJ/mol | CGC | Chickos, Hosseini, et al., 1995 | Based on data from 393. to 433. K.; AC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 88. ± 10. | kJ/mol | AVG | N/A | Average of 6 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
59.7 | 416. | A | Stephenson and Malanowski, 1987 | Based on data from 401. to 561. K.; AC |
59.7 | 432. | N/A | von Terres, Gebert, et al., 1955 | Based on data from 417. to 561. K.; AC |
61.8 | 473. | N/A | May, Berliner, et al., 1927, 2 | Based on data from 423. to 563. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
417. to 561. | 5.17907 | 2771.316 | -24.925 | von Terres, Gebert, et al., 1955, 2 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
97.8 | 305. | A | Stephenson and Malanowski, 1987 | Based on data from 298. to 312. K. See also Aihara, 1960.; AC |
87.8 | 323. | A | Stephenson and Malanowski, 1987 | In reference Aihara, 1960 the author mentions that there may be a small Phase transition at 39.1 °C as evidenced in the log P versus 1/T graph; AC |
87.4 ± 2.5 | 300. | ME | Arshadi, 1974 | Based on data from 277. to 324. K.; AC |
94.2 ± 0.5 | 305. to 323. | ME | Colomina, Roux, et al., 1974, 2 | AC |
78.66 ± 0.84 | 283. | V | Karyakin, Rabinovich, et al., 1968 | ALS |
68.2 | 567.85 | V | May, Berliner, et al., 1927, 3 | ALS |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
20.9 | 392.5 | DSC | Rojas and Orozco, 2003 | Based on data from 363. to 413. K.; AC |
18.79 | 393.6 | C | Acree, 1991 | See also Andrews, Lynn, et al., 1926, 2.; AC |
18.790 | 393.6 | N/A | Andrews, Lynn, et al., 1926, 2 | DH |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
55.9 | 393.6 | Andrews, Lynn, et al., 1926, 2 | DH |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Phase change 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
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-1515 |
NIST MS number | 229333 |
References
Go To: Top, Gas phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Ribeiro Da Silva, Ribeiro Da Silva, et al., 1988
Ribeiro Da Silva, M.A.V.; Ribeiro Da Silva, M.D.M.C.; Pilcher, G.,
Enthalpies of combustion of 1-hydroxynaphthalene, 2-hydroxynaphthalene, and 1,2-, 1,3-, 1,4-, and 2,3-dihydroxynaphthalenes,
J. Chem. Thermodyn., 1988, 20, 969-974. [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]
Colomina, Roux, et al., 1974, 2
Colomina, M.; Roux, M.V.; Turrion, C.,
Thermochemical properties of naphthalene compounds. II. Enthalpies of combustion and formation of the 1- and 2-naphthols,
J. Chem. Thermodyn., 1974, 6, 571-576. [all data]
Pushin, 1954
Pushin, N.A.,
Heats of combustion and heats of formation of isomeric organic compounds,
Bull. Soc. Chim. Belgrade, 1954, 19, 531-547. [all data]
Kudchadker S.A., 1978
Kudchadker S.A.,
Ideal gas thermodynamic properties of 1- and 2-naphthol,
J. Chem. Soc. Faraday Trans. 2, 1978, 74, 1515-1520. [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]
Mantyukov, Loginova, et al., 1974
Mantyukov, G.D.; Loginova, M.A.; Bychkov, B.N.; Rozhkov, S.S.,
Liquid-vapor equilibrium in the system isopropylnaphthalene + 2-naphthol,
J. Appl. Chem. USSR (Engl. Transl.), 1974, 47, 2665-6. [all data]
May, Berliner, et al., 1927
May, O.E.; Berliner, J.F.T.; Lynch, D.F.J.,
Studies in Vapor Pressure IV. The Naphthols,
J. Am. Chem. Soc., 1927, 49, 1012. [all data]
Andrews, Lynn, et al., 1926
Andrews, D.H.; Lynn, G.; Johnston, J.,
The Heat Capacities and Heat of Crystallization of Some Isomeric Aromatic Compounds,
J. Am. Chem. Soc., 1926, 48, 1274. [all data]
Chickos, Hosseini, et al., 1995
Chickos, James S.; Hosseini, Sarah; Hesse, Donald G.,
Determination of vaporization enthalpies of simple organic molecules by correlations of changes in gas chromatographic net retention times,
Thermochimica Acta, 1995, 249, 41-62, https://doi.org/10.1016/0040-6031(95)90670-3
. [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]
von Terres, Gebert, et al., 1955
von Terres, E.; Gebert, F.; Hulsemann, H.; Petereit, H.; Toepsch, H.; Ruppert, W.,
Brennst.-Chem., 1955, 36, 272. [all data]
May, Berliner, et al., 1927, 2
May, Orville E.; Berliner, J.F.T.; Lynch, D.F.J.,
STUDIES IN VAPOR PRESSURE. IV. THE NAPHTHOLS,
J. Am. Chem. Soc., 1927, 49, 4, 1012-1016, https://doi.org/10.1021/ja01403a018
. [all data]
von Terres, Gebert, et al., 1955, 2
von Terres, E.; Gebert, F.; Hulsemann, H.; Petereit, H.; Toepsch, H.; Ruppert, W.,
Zur Kenntnis der physikalisch-chemischen Grundlagen der Gewinnung und Zerlegung der Phenolfraktionen von Steinkohlenteer und Braunkohlenschwelteer. IV. Mitteilung Die Dampfdrucke von Phenol und Phenolderivaten,
Brennst.-Chem., 1955, 36, 272-274. [all data]
Aihara, 1960
Aihara, Ariyuki,
Estimation of the Energy of Hydrogen Bonds Formed in Crystals. II. Phenols,
Bull. Chem. Soc. Jpn., 1960, 33, 2, 194-200, https://doi.org/10.1246/bcsj.33.194
. [all data]
Arshadi, 1974
Arshadi, Mohammed R.,
Determination of heats of sublimation of organic compounds by a mass spectrometric--knudsen effusion method,
J. Chem. Soc., Faraday Trans. 1, 1974, 70, 0, 1569, https://doi.org/10.1039/f19747001569
. [all data]
Karyakin, Rabinovich, et al., 1968
Karyakin, N.V.; Rabinovich, I.B.; Pakhomov, L.G.,
Heats of sublimation of naphthalene and its monosubstituted β-derivatives,
Russ. J. Phys. Chem. (Engl. Transl.), 1968, 42, 954. [all data]
May, Berliner, et al., 1927, 3
May, O.E.; Berliner, J.F.T.; Lynch, D.F.J.,
Studies in vapor pressure. IV. The naphthols,
J. Am. Chem. Soc., 1927, 49, 1012-10. [all data]
Rojas and Orozco, 2003
Rojas, Aarón; Orozco, Eulogio,
Measurement of the enthalpies of vaporization and sublimation of solids aromatic hydrocarbons by differential scanning calorimetry,
Thermochimica Acta, 2003, 405, 1, 93-107, https://doi.org/10.1016/S0040-6031(03)00139-4
. [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]
Andrews, Lynn, et al., 1926, 2
Andrews, D.H.; Lynn, G.; Johnston, J.,
The heat capacities and heat of crystallization of some isomeric aromatic compounds,
J. Am. Chem. Soc., 1926, 48, 1274-1287. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas S°gas Entropy of gas at standard conditions Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion 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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