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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Phase change data
Go To: Top, Gas phase ion energetics data, Gas Chromatography, 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° | 91.2 | kJ/mol | N/A | Ribeiro Da Silva, Ribeiro Da Silva, et al., 1988 | DRB |
ΔsubH° | 91.17 ± 0.42 | kJ/mol | V | Colomina, Roux, et al., 1974 | ALS |
ΔsubH° | 91.1 | kJ/mol | N/A | Colomina, Roux, et al., 1974 | DRB |
ΔsubH° | 91.5 ± 3.8 | kJ/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 (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
58.5 | 414. | A | Stephenson and Malanowski, 1987 | Based on data from 399. to 556. K.; AC |
60.8 | 473. | N/A | May, Berliner, et al., 1927, 2 | Based on data from 423. to 563. K.; AC |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
93.3 | 305. | A | Stephenson and Malanowski, 1987 | Based on data from 298. to 312. K. See also Aihara, 1960.; AC |
84.3 | 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 |
89.1 ± 1.7 | 304. | ME | Arshadi, 1974 | Based on data from 279. to 328. K.; AC |
91.2 ± 0.4 | 296. to 313. | ME | Colomina, Roux, et al., 1974 | AC |
71.5 | 561.01 | V | May, Berliner, et al., 1927, 3 | ALS |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
23.3 | 368.7 | DSC | Rai, Pandey, et al., 2002 | AC |
24.4 | 369.7 | DSC | Rai and Rai, 1998 | AC |
23.01 | 369. | N/A | Acree, 1991 | AC |
23.220 | 369. | N/A | Pacor, 1967 | DH |
23.470 | 368.2 | N/A | Andrews, Lynn, et al., 1926, 2 | DH |
23.47 | 368.2 | C | Andrews, Lynn, et al., 1926, 2 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
62.9 | 369. | Pacor, 1967 | DH |
63.6 | 368.2 | Andrews, Lynn, et al., 1926, 2 | DH |
Gas phase ion energetics data
Go To: Top, Phase change data, Gas Chromatography, 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 |
Gas Chromatography
Go To: Top, 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
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | OV-1 | 150. | 1517. | Zhang, Chen, et al., 1997 | 25. m/0.2 mm/0.33 μm, N2 |
Capillary | OV-1 | 130. | 1487. | Erdmann, Rochholz, et al., 1992 | |
Capillary | OV-1 | 160. | 1484. | Erdmann, Rochholz, et al., 1992 | |
Packed | SE-30 | 200. | 1517. | Sellier, Tersac, et al., 1981 | Column length: 2. m |
Kovats' RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Packed | SE-30 | 1494. | Osselton and Snelling, 1986 | N2, Chromosorb W HP; Column length: 2. m; Program: not specified |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | SLB-5MS | 1510. | Mondello, Casilli, et al., 2007 | 30. m/0.25 mm/0.25 μm, He, 2. K/min; Tstart: 70. C; Tend: 300. C |
Capillary | SLB-5MS | 1517. | Mondello, Casilli, et al., 2007 | 30. m/0.25 mm/0.25 μm, He, 2. K/min; Tstart: 70. C; Tend: 300. C |
Capillary | OV-101 | 1473.7 | Ferchichi and Messadi, 1994 | 4. K/min; Column length: 25. m; Column diameter: 0.2 mm; Tstart: 30. C; Tend: 250. C |
Capillary | OV-101 | 1494.9 | Ferchichi and Messadi, 1994 | 4. K/min; Column length: 25. m; Column diameter: 0.2 mm; Tstart: 30. C; Tend: 250. C |
Capillary | DB-5 | 1516. | Rostad and Pereira, 1986 | 30. m/0.26 mm/0.25 μm, He, 50. C @ 4. min, 6. K/min, 300. C @ 20. min |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | 5 % Phenyl methyl siloxane | 1504. | Yasuhara, Shiraishi, et al., 1997 | 25. m/0.31 mm/0.52 μm, He; Program: 50C(2min) => (20C/min) => 120C => (7C/min) => 310C(10min) |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 1525. | Amorim, Dimandja, et al., 2009 | 30. m/0.25 mm/0.25 μm, Hydrogen, 70. C @ 0.5 min, 5. K/min, 280. C @ 17.5 min |
Capillary | Ultra-1 | 1464. | Okumura, 1991 | 25. m/0.32 mm/0.25 μm, He, 3. K/min; Tstart: 80. C; Tend: 260. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Polydimethyl siloxane, unknown content of Ph-groups | 1514. | Geldon, 1989 | Program: not specified |
Capillary | Polydimethyl siloxane, unknown content of Ph-groups | 1516. | Geldon, 1989 | Program: not specified |
Other | Methyl Silicone | 1490. | Ardrey and Moffat, 1981 | Program: not specified |
Lee's RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5 | 259.66 | Pedersen, Durant, et al., 2005 | 30. m/0.25 mm/0.25 μm, Helium, 50. C @ 1.5 min, 6. K/min, 310. C @ 10. min |
Capillary | DB-5 | 258.48 | Williams and Horne, 1995 | He, 60. C @ 2. min, 5. K/min; Column length: 25. m; Column diameter: 0.3 mm; Tend: 270. C |
Capillary | SPB-5 | 258.5 | Knobloch and Engewald, 1993 | 40. C @ 2. min, 4. K/min; Column length: 30. m; Column diameter: 0.25 mm; Tend: 300. C |
Capillary | DB-5 | 258.80 | Rostad and Pereira, 1986 | 30. m/0.26 mm/0.25 μm, He, 50. C @ 4. min, 6. K/min, 300. C @ 20. min |
References
Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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,
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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. II. Enthalpies of combustion and formation of the 1- and 2-naphthols,
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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,
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Cox and Pilcher, 1970
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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,
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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,
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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,
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. [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
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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
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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]
Zhang, Chen, et al., 1997
Zhang, M.; Chen, B.; Shen, S.; Chen, S.,
Compositional studies of high-temperature coal tar by g.c.-FT-i.r. analysis of middle oil fractions,
Fuel, 1997, 76, 5, 415-423, https://doi.org/10.1016/S0016-2361(97)85518-4
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Erdmann, Rochholz, et al., 1992
Erdmann, F.; Rochholz, G.; Schütz, H.,
Retention-indices on OV-1 of approximately 170 commonly used pesticides,
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Sellier, Tersac, et al., 1981
Sellier, F.; Tersac, G.; Guiochon, G.,
Étude de la polarité d'un poly(oxy aryl sulfonyl arylène) utilisé comme phase stationnaire en chromatographie gaz-liquide,
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Osselton and Snelling, 1986
Osselton, M.D.; Snelling, R.D.,
Chromatographic Identification of Pesticides,
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Mondello, Casilli, et al., 2007
Mondello, L.; Casilli, A.; Tranchida, P.Q.; Presti, M.L.; Dugo, P.; Dugo, G.,
Comprehensive gas chromatography coupled to mass spectrometry for the separation of pesticides in a very complex matrix,
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Ferchichi and Messadi, 1994
Ferchichi, L.; Messadi, D.,
Simulations de la rétention et de l'effecacité de colonne en chromatographie en phase gazeuse à température programmée: théorie et application,
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Rostad and Pereira, 1986
Rostad, C.E.; Pereira, W.E.,
Kovats and Lee retention indices determined by gas chromatography/mass spectrometry for organic compounds of environmental interest,
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Yasuhara, Shiraishi, et al., 1997
Yasuhara, A.; Shiraishi, H.; Nishikawa, M.; Yamamoto, T.; Uehiro, T.; Nakasugi, O.; Okumura, T.; Kenmotsu, K.; Fukui, H.; Nagase, M.; Ono, Y.; Kawagoshi, Y.; Baba, K.; Noma, Y.,
Determination of organic components in leachates from hazardous waste disposal sites in Japan by gas chromatography-mass spectrometry,
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Amorim, Dimandja, et al., 2009
Amorim, L.C.A.; Dimandja, J.-M.; Cardeal, Z. de.L.,
Analysis of hydroxylated polycyclic aromatoc hydrocarbons in urine using comprehensive two-dimensional gas chromatography with a flame ionization detector,
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Okumura, T.,
retention indices of environmental chemicals on methyl silicone capillary column,
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Geldon, 1989
Geldon, A.L.,
Ground Water Hydrology of the Central Raton Basin, Colorado and New Mexico, US Geological Survey, US Government Printing Office, 1989, 104. [all data]
Ardrey and Moffat, 1981
Ardrey, R.E.; Moffat, A.C.,
Gas-liquid chromatographic retention indices of 1318 substances of toxicological interest on SE-30 or OV-1 stationary phase,
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Pedersen, Durant, et al., 2005
Pedersen, D.U.; Durant, J.L.; Taghizadeh, K.; Hemond, H.F.; Lafleur, A.L.; Cass, G.R.,
Human cell mutagenes in respirable airborne particles from the Northeastern United States. 2. Quantification of mutagenes and other organic compounds.,
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Williams, P.T.; Horne, P.A.,
Analysis of aromatic hydrocarbons in pyrolytic oil derived from biomass,
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Knobloch and Engewald, 1993
Knobloch, T.; Engewald, W.,
Identification of some polar polycyclic compounds in emissions from brown-coal-fired residential stoves,
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Notes
Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature 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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