1-Naphthalenol

Formula: C₁₀H₈O
Molecular weight: 144.1699
IUPAC Standard InChI: InChI=1S/C10H8O/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7,11H
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

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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
Δ_fH°_gas	-30.8 ± 1.6	kJ/mol	Ccb	Ribeiro Da Silva, Ribeiro Da Silva, et al., 1988	Hs=91.2±0.4 kJ/mol; Colomina, Roux, et al., 1974; ALS
Δ_fH°_gas	-29.9 ± 1.1	kJ/mol	Ccb	Colomina, Roux, et al., 1974, 2	ALS
Δ_fH°_gas	-4.3	kJ/mol	N/A	Pushin, 1954	Value computed using Δ_fH_solid° value of -95.4 kj/mol from Pushin, 1954 and Δ_subH° value of 91.1 kj/mol from Pushin, 1954.; DRB

Constant pressure heat capacity of gas

C_p,gas (J/mol*K)	Temperature (K)	Reference	Comment
37.44	50.	Kudchadker S.A., 1978	GT
53.10	100.
73.93	150.
98.14	200.
136.34	273.15
149.44	298.15
150.40	300.
199.15	400.
239.47	500.
271.50	600.
297.01	700.
317.66	800.
334.68	900.
348.91	1000.
360.92	1100.
371.14	1200.
379.88	1300.
387.41	1400.
393.92	1500.

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
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity	Value	Units	Method	Reference	Comment
T_boil	552.2	K	N/A	Aldrich Chemical Company Inc., 1990	BS
T_boil	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
T_fus	368. ± 2.	K	AVG	N/A	Average of 9 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
T_triple	368.2	K	N/A	Andrews, Lynn, et al., 1926	Uncertainty assigned by TRC = 0.3 K; TRC
Quantity	Value	Units	Method	Reference	Comment
Δ_subH°	91.2	kJ/mol	N/A	Ribeiro Da Silva, Ribeiro Da Silva, et al., 1988	DRB
Δ_subH°	91.17 ± 0.42	kJ/mol	V	Colomina, Roux, et al., 1974, 2	ALS
Δ_subH°	91.1	kJ/mol	N/A	Colomina, Roux, et al., 1974, 2	DRB
Δ_subH°	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

Δ_vapH (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

Δ_subH (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, 2	AC
71.5	561.01	V	May, Berliner, et al., 1927, 3	ALS

Enthalpy of fusion

Δ_fusH (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

Δ_fusS (J/mol*K)	Temperature (K)	Reference	Comment
62.9	369.	Pacor, 1967	DH
63.6	368.2	Andrews, Lynn, et al., 1926, 2	DH

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:

Gas phase ion energetics data

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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

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

SOLUTION (SATURATED IN CCl4 FOR 4000-1340 CM^-1, SATURATED IN CS2 FOR 1370-600 CM^-1); BECKMAN IR-7 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Gas Chromatography

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Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

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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

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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

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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; T_start: 70. C; T_end: 300. C
Capillary	SLB-5MS	1517.	Mondello, Casilli, et al., 2007	30. m/0.25 mm/0.25 μm, He, 2. K/min; T_start: 70. C; T_end: 300. C
Capillary	OV-101	1473.7	Ferchichi and Messadi, 1994	4. K/min; Column length: 25. m; Column diameter: 0.2 mm; T_start: 30. C; T_end: 250. C
Capillary	OV-101	1494.9	Ferchichi and Messadi, 1994	4. K/min; Column length: 25. m; Column diameter: 0.2 mm; T_start: 30. C; T_end: 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

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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

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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; T_start: 80. C; T_end: 260. C

Normal alkane RI, non-polar column, custom temperature program

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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

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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; T_end: 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; T_end: 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, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, Notes

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]

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 . [all data]

Erdmann, Rochholz, et al., 1992
Erdmann, F.; Rochholz, G.; Schütz, H., Retention-indices on OV-1 of approximately 170 commonly used pesticides, Mikrochim. Acta, 1992, 106, 3-6, 219-226, https://doi.org/10.1007/BF01242093 . [all data]

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, J. Chromatogr., 1981, 219, 2, 213-224, https://doi.org/10.1016/S0021-9673(00)87931-5 . [all data]

Osselton and Snelling, 1986
Osselton, M.D.; Snelling, R.D., Chromatographic Identification of Pesticides, J. Chromatogr., 1986, 368, 265-271, https://doi.org/10.1016/S0021-9673(00)91068-9 . [all data]

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, Anal. Bioanal. Chem., 2007, 389, 6, 1755-1763, https://doi.org/10.1007/s00216-007-1412-y . [all data]

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, Analusis, 1994, 22, 392-399. [all data]

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, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1986, 9, 6, 328-334, https://doi.org/10.1002/jhrc.1240090603 . [all data]

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, J. Chromatogr. A, 1997, 774, 1-2, 321-332, https://doi.org/10.1016/S0021-9673(97)00078-2 . [all data]

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, J. Chromatogr. A., 2009, 1216, 14, 2900-2904, https://doi.org/10.1016/j.chroma.2008.11.012 . [all data]

Okumura, 1991
Okumura, T., retention indices of environmental chemicals on methyl silicone capillary column, Journal of Environmental Chemistry (Japan), 1991, 1, 2, 333-358, https://doi.org/10.5985/jec.1.333 . [all data]

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, J. Chromatogr., 1981, 220, 3, 195-252, https://doi.org/10.1016/S0021-9673(00)81925-1 . [all data]

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., Environ. Sci. Technol., 2005, 39, 24, 9547-9560, https://doi.org/10.1021/es050886c . [all data]

Williams and Horne, 1995
Williams, P.T.; Horne, P.A., Analysis of aromatic hydrocarbons in pyrolytic oil derived from biomass, J. Anal. Appl. Pyrolysis, 1995, 31, 15-37, https://doi.org/10.1016/0165-2370(94)00814-H . [all data]

Knobloch and Engewald, 1993
Knobloch, T.; Engewald, W., Identification of some polar polycyclic compounds in emissions from brown-coal-fired residential stoves, J. Hi. Res. Chromatogr., 1993, 16, 4, 239-242, https://doi.org/10.1002/jhrc.1240160407 . [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, References

Symbols used in this document:

AE	Appearance energy
C_p,gas	Constant pressure heat capacity of gas
IE (evaluated)	Recommended ionization energy
T_boil	Boiling point
T_fus	Fusion (melting) point
T_triple	Triple point temperature
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fusH	Enthalpy of fusion
Δ_fusS	Entropy 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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