1-Naphthalenol
- Formula: C10H8O
- Molecular weight: 144.1699
- IUPAC Standard InChIKey: KJCVRFUGPWSIIH-UHFFFAOYSA-N
- CAS Registry Number: 90-15-3
- 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: 1-Naphthol; α-Hydroxynaphthalene; α-Naphthol; Basf Ursol ERN; C.I. Oxidation Base 33; C.I. 76605; Durafur Developer D; Fouramine ERN; Fourrine ERN; Fourrine 99; Furro ER; Nako TRB; Tertral ERN; Ursol ERN; Zoba ERN; 1-Hydroxynaphthalene; NSC 9586
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Gas phase thermochemistry data
Go To: Top, Phase change data, Gas phase ion energetics 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 | -7.36 ± 0.38 | kcal/mol | Ccb | Ribeiro Da Silva, Ribeiro Da Silva, et al., 1988 | Hs=91.2±0.4 kJ/mol; Colomina, Roux, et al., 1974; ALS |
ΔfH°gas | -7.14 ± 0.26 | kcal/mol | Ccb | Colomina, Roux, et al., 1974, 2 | ALS |
ΔfH°gas | -1.0 | kcal/mol | N/A | Pushin, 1954 | Value computed using ΔfHsolid° value of -95.4 kj/mol from Pushin, 1954 and ΔsubH° value of 91.1 kj/mol from Pushin, 1954.; DRB |
Constant pressure heat capacity of gas
Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
8.948 | 50. | Kudchadker S.A., 1978 | GT |
12.69 | 100. | ||
17.67 | 150. | ||
23.46 | 200. | ||
32.586 | 273.15 | ||
35.717 | 298.15 | ||
35.946 | 300. | ||
47.598 | 400. | ||
57.235 | 500. | ||
64.890 | 600. | ||
70.987 | 700. | ||
75.923 | 800. | ||
79.990 | 900. | ||
83.391 | 1000. | ||
86.262 | 1100. | ||
88.705 | 1200. | ||
90.793 | 1300. | ||
92.593 | 1400. | ||
94.149 | 1500. |
Phase change data
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics 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 | 552.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 561.16 | K | N/A | May, Berliner, et al., 1927 | Uncertainty assigned by TRC = 0.15 K; probably calculated from vapor pressure equation; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 368. ± 2. | K | AVG | N/A | Average of 9 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 368.2 | K | N/A | Andrews, Lynn, et al., 1926 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 21.8 | kcal/mol | N/A | Ribeiro Da Silva, Ribeiro Da Silva, et al., 1988 | DRB |
ΔsubH° | 21.79 ± 0.10 | kcal/mol | V | Colomina, Roux, et al., 1974, 2 | ALS |
ΔsubH° | 21.8 | kcal/mol | N/A | Colomina, Roux, et al., 1974, 2 | DRB |
ΔsubH° | 21.9 ± 0.91 | kcal/mol | B | Andrews, Lynn, et al., 1926, 2 | See also Cox and Pilcher, 1970 and May, Berliner, et al., 1927, 2.; AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
14.0 | 414. | A | Stephenson and Malanowski, 1987 | Based on data from 399. to 556. K.; AC |
14.5 | 473. | N/A | May, Berliner, et al., 1927, 2 | Based on data from 423. to 563. K.; AC |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
22.3 | 305. | A | Stephenson and Malanowski, 1987 | Based on data from 298. to 312. K. See also Aihara, 1960.; AC |
20.1 | 319. | A | Stephenson and Malanowski, 1987 | In Ref. Aihara, 1960 the author mentions that there may be a small phase transition at 39.4 °C as evidenced in the log P versus 1/T graph; AC |
21.3 ± 0.41 | 304. | ME | Arshadi, 1974 | Based on data from 279. to 328. K.; AC |
21.8 ± 0.1 | 296. to 313. | ME | Colomina, Roux, et al., 1974, 2 | AC |
17.1 | 561.01 | V | May, Berliner, et al., 1927, 3 | ALS |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
5.57 | 368.7 | DSC | Rai, Pandey, et al., 2002 | AC |
5.83 | 369.7 | DSC | Rai and Rai, 1998 | AC |
5.500 | 369. | N/A | Acree, 1991 | AC |
5.5497 | 369. | N/A | Pacor, 1967 | DH |
5.6095 | 368.2 | N/A | Andrews, Lynn, et al., 1926, 2 | DH |
5.609 | 368.2 | C | Andrews, Lynn, et al., 1926, 2 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
15.0 | 369. | Pacor, 1967 | DH |
15.2 | 368.2 | Andrews, Lynn, et al., 1926, 2 | DH |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, 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 evaluated as indicated in comments:
L - Sharon G. Lias
Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 7.76 ± 0.03 | eV | N/A | N/A | L |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
7.76 ± 0.03 | PI | Potapov, Kardash, et al., 1972 | LLK |
7.78 | PE | Utsunomiya, Kobayashi, et al., 1975 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C9H7+ | 13.68 | CO+H | EI | Occolowitz and White, 1968 | RDSH |
C9H8+ | 11.73 | CO | EI | Occolowitz and White, 1968 | RDSH |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics 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
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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-6154 |
NIST MS number | 228210 |
References
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics 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]
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]
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]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [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]
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]
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]
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]
Rai, Pandey, et al., 2002
Rai, U.S.; Pandey, Pinky; Rai, R.N.,
Physical chemistry of binary organic eutectic and monotectic alloys; 1,2,4,5-tetrachlorobenzene--α-naphthol and TCB--resorcinol systems,
Materials Letters, 2002, 53, 1-2, 83-90, https://doi.org/10.1016/S0167-577X(01)00458-X
. [all data]
Rai and Rai, 1998
Rai, U.S.; Rai, R.N.,
Journal of Thermal Analysis and Calorimetry, 1998, 53, 3, 883-893, https://doi.org/10.1023/A:1010190402954
. [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]
Pacor, 1967
Pacor, P.,
Applicability of the DuPont 900 DTA apparatus in quantitative differential thermal analysis,
Anal. Chim. Acta, 1967, 37, 200-208. [all data]
Potapov, Kardash, et al., 1972
Potapov, V.K.; Kardash, I.E.; Sorokin, V.V.; Sokolov, S.A.; Evlasheva, T.I.,
Photoionization of heteroaromatic compounds,
Khim. Vys. Energ., 1972, 6, 392. [all data]
Utsunomiya, Kobayashi, et al., 1975
Utsunomiya, C.; Kobayashi, T.; Nagakura, S.,
Photoelectron spectra of substituted naphthalenes,
Bull. Chem. Soc. Jpn., 1975, 48, 1852. [all data]
Occolowitz and White, 1968
Occolowitz, J.L.; White, G.L.,
Energetic considerations in the assignment of some fragment ion structures,
Australian J. Chem., 1968, 21, 997. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas IE (evaluated) Recommended ionization energy 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 - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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