Phenol

• Formula: C₆H₆O
• Molecular weight: 94.1112
• IUPAC Standard InChI: InChI=1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H Copy

  
• IUPAC Standard InChIKey: ISWSIDIOOBJBQZ-UHFFFAOYSA-N Copy
• CAS Registry Number: 108-95-2
• 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.
• Isotopologues:
  • Phenol-d6-
• Other names: Carbolic acid; Baker's P and S Liquid and Ointment; Benzenol; Hydroxybenzene; Izal; Monohydroxybenzene; Monophenol; Oxybenzene; Phenic acid; Phenyl alcohol; Phenyl hydrate; Phenyl hydroxide; Phenylic acid; Phenylic alcohol; PhOH; Benzene, hydroxy-; Acide carbolique; Baker's P & S liquid & Ointment; Fenol; Fenolo; NCI-C50124; Paoscle; Phenole; Carbolsaure; NA 2821; Phenol alcohol; Phenol, molten; Rcra waste number U188; UN 1671; UN 2312; UN 2821; Phenic alcohol; NSC 36808; Campho-Phenique Cold Sore Gel (Salt/Mix); Campho-Phenique Gel (Salt/Mix); Campho-Phenique Liquid (Salt/Mix)
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• Information on this page:
  • Condensed phase thermochemistry data
  • Henry's Law data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
  • X-ray Photoelectron Spectroscopy Database, version 5.0
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Condensed phase thermochemistry data

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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
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of solid

Henry's Law data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Rolf Sander

Henry's Law constant (water solution)

k_H(T) = k°_H exp(d(ln(k_H))/d(1/T) ((1/T) - 1/(298.15 K)))
k°_H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(k_H))/d(1/T) = Temperature dependence constant (K)

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• SOLUTION (10% IN CCl4 FOR 3800-1300, 10% IN CS2 FOR 1300-650, 10% IN CCl4 FOR 650-250 CM^-1) VERSUS SOLVENT; PERKIN-ELMER 521 (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

Mass spectrum (electron ionization)

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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

UV/Visible spectrum

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

Gas Chromatography

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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

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Kovats' RI, non-polar column, temperature ramp

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Kovats' RI, polar column, isothermal

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Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Van Den Dool and Kratz RI, non-polar column, custom temperature program

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Van Den Dool and Kratz RI, polar column, temperature ramp

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Van Den Dool and Kratz RI, polar column, custom temperature program

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Normal alkane RI, non-polar column, isothermal

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Normal alkane RI, non-polar column, temperature ramp

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

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Normal alkane RI, polar column, temperature ramp

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Normal alkane RI, polar column, custom temperature program

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Lee's RI, non-polar column, temperature ramp

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Lee's RI, non-polar column, custom temperature program

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References

Go To: Top, Condensed phase thermochemistry data, Henry's Law data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Cox, 1961
Cox, J.D., The heats of combustion of phenol and the three cresols, Pure Appl. Chem., 1961, 2, 125-128. [all data]

Andon, Biddiscombe, et al., 1960
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Parks, Manchester, et al., 1954
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Badoche, 1941
Badoche, M., No 19. - Chaleurs de combustion du phenol, du-m-cresol et del leurs ethers; par M. Marius BADOCHE., Bull. Soc. Chim. Fr., 1941, 8, 212-220. [all data]

Andon, Counsell, et al., 1963
Andon, R.J.L.; Counsell, J.F.; Herington, E.F.G.; Martin, J.F., Thermodynamic properties of organic oxygen compounds, Trans. Faraday Soc., 1963, 59, 830-835. [all data]

Parks, Huffman, et al., 1933
Parks, G.S.; Huffman, H.M.; Barmore, M., Thermal data on organic compounds. XI. The heat capacities, entropies and free energies of ten compounds containing oxygen or nitrogen. J. Am. Chem. Soc., 1933, 55, 2733-2740. [all data]

Nichols and Wads, 1975
Nichols, N.; Wads, I., Thermochemistry of solutions of biochemical model compounds. 3. Some benzene derivatives in aqueous solution, J. Chem. Thermodynam., 1975, 7, 329-336. [all data]

Rastorguev and Ganiev, 1967
Rastorguev, Yu.L.; Ganiev, Yu.A., Study of the heat capacity of selected solvents, Izv. Vyssh. Uchebn. Zaved. Neft Gaz. 10, 1967, No.1, 79-82. [all data]

Campbell and Campbell, 1940
Campbell, A.N.; Campbell, A.J.R., The heats of solution, heats of formation, specific heats and equilibrium diagrams of certain molecular compounds. J. Am. Chem. Soc., 1940, 62, 291-297. [all data]

Aoyama and Kanda, 1935
Aoyama, S.; Kanda, E., Studies on the heat capacities at low temperature. Report I. Heat capacities of some organic substances at low temperature, Sci. Rept. Tohoku Imp. Univ. [1]24, 1935, 107-115. [all data]

Howe, Mullins, et al., 1987
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Martynoff, 1949
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Berezkin, Popova, et al., 1997
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Zhang, Chen, et al., 1997
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Righezza, Hassani, et al., 1996
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Hassani and Meklati, 1992
Hassani, A.; Meklati, B.Y., Gas chromatographic behaviour of monosubstituted benzenes, benzaldehydes and acetophenones on OV polymethylphenyl-silicone stationary phases, Chromatographia, 1992, 33, 5/6, 267-271, https://doi.org/10.1007/BF02276193 . [all data]

Zhang, Li, et al., 1992
Zhang, M.J.; Li, S.D.; Chen, B.J., Compositional studies of high-temperature coal tar by GC/FTIR analysis of light oil fractions, Chromatographia, 1992, 33, 3/4, 138-146, https://doi.org/10.1007/BF02275894 . [all data]

Evans and Haken, 1989
Evans, M.B.; Haken, J.K., Dispersion and selectivity indices in gas chromatography. IV. Chlorinated aromatic compounds, J. Chromatogr., 1989, 468, 373-382, https://doi.org/10.1016/S0021-9673(00)96332-5 . [all data]

Engewald, Billing, et al., 1988
Engewald, W.; Billing, U.; Topalova, I.; Petsev, N., Structure-retention correlations of alkylphenols in gas-liquid and gas-solid chromatography, J. Chromatogr., 1988, 446, 71-77, https://doi.org/10.1016/S0021-9673(00)94419-4 . [all data]

Shakirov, Tsypysheva, et al., 1988
Shakirov, L.G.; Tsypysheva, L.G.; Suleimamova, R.A.; Naimushin, A.I.; Tsypyshev, O.Yu., Gas chromatographic determination of the products of the synthesis of chlorine-substituted salicylic acids, Zh. Anal. Khim., 1988, 43, 143-146. [all data]

Korhonen and Knuutinen, 1984
Korhonen, I.O.O.; Knuutinen, J., Gas-liquid chromatographic analyses. XXVII. Separation of chlorinated 4-hydroxybenzaldehydes on a capillary column coated with non-polar SE-30 stationary phase, J. Chromatogr., 1984, 292, 2, 345-353, https://doi.org/10.1016/S0021-9673(01)83614-1 . [all data]

Korhonen, 1984
Korhonen, I.O.O., Gas-liquid chromatographic analyses. XXXI. Retention increments of isomeric chlorophenols on low-polarity (SE-30) and polar (FFAP) capillary columns, J. Chromatogr., 1984, 315, 185-200, https://doi.org/10.1016/S0021-9673(01)90736-8 . [all data]

Tiess, 1984
Tiess, D., Gaschromatographische Retentionsindices von 125 leicht- bis mittelflüchtigen organischen Substanzen toxikologisch-analytischer Relevanz auf SE-30, Wiss. Z. Wilhelm-Pieck-Univ. Rostock Math. Naturwiss. Reihe, 1984, 33, 6-9. [all data]

Winskowski, 1983
Winskowski, J., Gaschromatographische Identifizierung von Stoffen anhand von Indexziffem und unterschiedlichen Detektoren, Chromatographia, 1983, 17, 3, 160-165, https://doi.org/10.1007/BF02271041 . [all data]

Zygmunt, Wardencki, et al., 1983
Zygmunt, B.; Wardencki, W.; Staszewski, R., Gas chromatographic identification of thiols in the naphta cut from Libyan crude oil, J. Chromatogr., 1983, 265, 136-138, https://doi.org/10.1016/S0021-9673(01)96709-3 . [all data]

Vernon and Edwards, 1975
Vernon, F.; Edwards, G.T., Gas-liquid chromatography on fluorinated stationary phases. II. Fluorinated compounds containing a functional group, J. Chromatogr., 1975, 114, 1, 87-93, https://doi.org/10.1016/S0021-9673(00)85245-0 . [all data]

Agr, Tesaric, et al., 1973
Agr, X.X.; Tesaric, K.; Janak, J., Will be entered later, J. Chromatogr., 1973, 95, 207-215. [all data]

Mitchell and Vernon, 1972
Mitchell, P.T.; Vernon, F., Gas-Liquid Chromatography of Nitrophenols and Methyl Derivatives, J. Chromatogr., 1972, 65, 3, 487-491, https://doi.org/10.1016/S0021-9673(00)84994-8 . [all data]

Tibor and Anna, 1971
Tibor, T.; Anna, B., Gázkromatográfiás retenció és a kémiai szerkezet, I., Magy. Kem. Foly., 1971, 77, 576-587. [all data]

Brown, Chapman, et al., 1968
Brown, I.; Chapman, I.L.; Nicholson, G.J., Gas chromatography of polar solutes in electron acceptor stationary phases, Aust. J. Chem., 1968, 21, 5, 1125-1141, https://doi.org/10.1071/CH9681125 . [all data]

Reymond, Mueggler-Chavan, et al., 1966
Reymond, D.; Mueggler-Chavan, F.; Viani, R.; Vuataz, L.; Egli, R.H., Gas chromatographic analysis of steam volatile aroma constituents: application to coffee, tea and cocoa aromas, J. Gas Chromatogr., 1966, 4, 1, 28-31, https://doi.org/10.1093/chromsci/4.1.28 . [all data]

Viani, Müggler-Chavan, et al., 1965
Viani, R.; Müggler-Chavan, F.; Reymond, D.; Egli, R.H., 196. Sur la composition de l'arôme de café, Helv. Chim. Acta, 1965, 48, 195-196, 1809-1815, https://doi.org/10.1002/hlca.19650480743 . [all data]

Medvedovskaya, Tikhomirova, et al., 1997
Medvedovskaya, I.I.; Tikhomirova, S.V.; Krasavina, T.D.; Gubkina, L.N., Comparison of results of chromatographic identification of complex mixtures of organic compounds, Proc. Omsk. Univ., 1997, 4, 34-36. [all data]

Still and Whitehead, 1977
Still, R.H.; Whitehead, A., Thermal degradation of polymers. XV. Vacuum pyrolysis studies on poly(p-methoxystyrene) and poly(p-hydroxystyrene), J. Appl. Polym. Sci., 1977, 21, 5, 1199-1213, https://doi.org/10.1002/app.1977.070210504 . [all data]

Anderson, Jurel, et al., 1973
Anderson, A.; Jurel, S.; Shymanska, M.; Golender, L., Gas-liquid chromatography of some aliphatic and heterocyclic mono- and pollyfunctional amines. VII. Retention indices of amines in some polar and unpolar stationary phases, Latv. PSR Zinat. Akad. Vestis Kim. Ser., 1973, 1, 51-63. [all data]

Ádámová, Orinák, et al., 2005
Ádámová, M.; Orinák, A.; Halás, L., Retention indices as identification tool in pyrolysis-capillary gas chromatography, J. Chromatogr. A, 2005, 1087, 1-2, 131-141, https://doi.org/10.1016/j.chroma.2005.01.003 . [all data]

Hierro, de la Hoz, et al., 2004
Hierro, E.; de la Hoz, L.; Ordóñez, J.A., Headspace volatile compounds from salted and occasionally smoked dried meats (cecinas) as affected by animal species, Food Chem., 2004, 85, 4, 649-657, https://doi.org/10.1016/j.foodchem.2003.07.001 . [all data]

Lalel, Singh, et al., 2003
Lalel, H.J.D.; Singh, Z.; Chye Tan, S., Glycosidically-bound aroma volatile compounds in the skin and pulp of 'Kensington Pride' mango fruit at different stages of maturity, Postharvest Biol. Technol., 2003, 29, 2, 205-218, https://doi.org/10.1016/S0925-5214(02)00250-8 . [all data]

Sun and Stremple, 2003
Sun, G.; Stremple, P., Retention index characterization of flavor, fragrance, and many other compounds on DB-1 and DB-XLB, 2003, retrieved from http://www.chem.agilent.com/cag/cabu/pdf/b-0279.pdf. [all data]

Xu, van Stee, et al., 2003
Xu, X.; van Stee, L.L.P.; Williams, J.; Beens, J.; Adahchour, M.; Vreuls, R.J.J.; Brinkman, U.A.Th.; Lelieveld, J., Comprehensive two-dimensional gas chromatography (GC×GC) measurements of volatile organic compounds in the atmosphere, Atmos. Chem. Phys., 2003, 3, 3, 665-682, https://doi.org/10.5194/acp-3-665-2003 . [all data]

Pino, Marbot, et al., 2002
Pino, J.A.; Marbot, R.; Bello, A., Volatile compounds of Psidium salutare (H.B.K.) Berg. fruit, J. Agric. Food Chem., 2002, 50, 18, 5146-5148, https://doi.org/10.1021/jf0116303 . [all data]

Kim, 2001
Kim, J.S., Einfluss der Temperatur beim Rösten von Sesam auf Aroma und antioxidative Eigenschaften des Öls, PhD Thesis, Technischen Universität Berlin zur Erlangung des akademischen Grades, Berlin, 2001, 151. [all data]

de Lacy Costello, Evans, et al., 2001
de Lacy Costello, B.P.J.; Evans, P.; Ewen, R.J.; Gunson, H.E.; Jones, P.R.H.; Ratcliffe, N.M.; Spencer-Phillips, P.T.N., Gas chromatography-mass spectrometry analyses of volatile organic compounds from potato tubers inoculated with Phytophthora infestans or Fusarium coeruleum, Plant Pathol., 2001, 50, 4, 489-496, https://doi.org/10.1046/j.1365-3059.2001.00594.x . [all data]

Yin, Xiu, et al., 2001
Yin, W.; Xiu, Z.; Aijin, H., Analysis of the volatile components in trogopterorum feces by capillary gas chromatography and gas chromatography/mass spectrometry, Fenxi Huaxue, 2001, 29, 2, 195-198. [all data]

Chevance and Farmer, 1999
Chevance, F.F.V.; Farmer, L.J., Identification of major volatile odor compounds in frankfurters, J. Agric. Food Chem., 1999, 47, 12, 5151-5160, https://doi.org/10.1021/jf990515d . [all data]

Helmig, Klinger, et al., 1999
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DeMilo, Lee, et al., 1996
DeMilo, A.B.; Lee, C.-J.; Moreno, D.S.; Martinez, A.J., Identification of volatiles derived from Citrobacter freundii fermentation of a trypticase soy broth, J. Agric. Food Chem., 1996, 44, 2, 607-612, https://doi.org/10.1021/jf950525o . [all data]

Gautzsch and Zinn, 1996
Gautzsch, R.; Zinn, P., Use of incremental models to estimate the retention indexes of aromatic compounds, Chromatographia, 1996, 43, 3/4, 163-176, https://doi.org/10.1007/BF02292946 . [all data]

Helmig, Pollock, et al., 1996
Helmig, D.; Pollock, W.; Greenberg, J.; Zimmerman, P., Gas chromatography mass spectrometry analysis of volatile organic trace gases at Mauna Loa Observatory, Hawaii, J. Geophys. Res., 1996, 101, D9, 14697-14710, https://doi.org/10.1029/96JD00212 . [all data]

Coen, Engel, et al., 1995
Coen, M.; Engel, R.; Nahrstedt, A., Chavicol β-D-glucoside, a phenylpropanoid heteroside, benzyl-β-D-glucoside and glycosidically bound volatiles from subspecies of Cedronella canariensis, Phytochemistry, 1995, 40, 1, 149-155, https://doi.org/10.1016/0031-9422(95)00241-X . [all data]

Gerbino and Castello, 1995
Gerbino, T.C.; Castello, G., Prediction of programmed temperature retention indices on capillary columns of different polarities, J. Chromatogr. A, 1995, 699, 1-2, 161-171, https://doi.org/10.1016/0021-9673(95)00024-H . [all data]

Lee, DeMilo, et al., 1995
Lee, C.-J.; DeMilo, A.B.; Moreno, D.S.; Martinez, A.J., Analysis of the volatile components of a bacterial fermentation that is attractive to the Mexican fruit fly, Anastrepha ludens, J. Agric. Food Chem., 1995, 43, 5, 1348-1351, https://doi.org/10.1021/jf00053a041 . [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]

Kaiser and Siegl, 1994
Kaiser, E.W.; Siegl, W.O., High resolution gas chromatographic determination of the atmospheric reactivity of engine-out hydrocarbon emissions from a spark-ignited engine, J. Hi. Res. Chromatogr., 1994, 17, 4, 264-270, https://doi.org/10.1002/jhrc.1240170414 . [all data]

Wu, Kuo, et al., 1991
Wu, P.; Kuo, M.-C.; Hartman, T.G.; Rosen, R.T.; Ho, C.-T., Free and glycosidically bound aroma compounds in pineapple (Ananas comosus L. Merr.), J. Agric. Food Chem., 1991, 39, 1, 170-172, https://doi.org/10.1021/jf00001a033 . [all data]

Shapi and Hesso, 1990
Shapi, M.M.; Hesso, A., Thermal decomposition of polystyrene volatile compounds from large-scale pyrolysis, J. Anal. Appl. Pyrolysis, 1990, 18, 2, 143-161, https://doi.org/10.1016/0165-2370(90)80004-8 . [all data]

Tang, Zhang, et al., 1990
Tang, J.; Zhang, Y.; Hartman, T.G.; Rosen, R.T.; Ho, C.-T., Free and glycosidically bound volatile compounds in fresh celery (Apium graveolens L.), J. Agric. Food Chem., 1990, 38, 10, 1937-1940, https://doi.org/10.1021/jf00100a013 . [all data]

Sagrero-Nieves, de Pooter, et al., 1989
Sagrero-Nieves, L.; de Pooter, H.L.; Van Wassenhove, F.A., Major Volatile Constituents from the Fruit of Mammee Apple (Mammea americana L.), J. Food Comp. Anal., 1989, 2, 4, 382-385, https://doi.org/10.1016/0889-1575(89)90010-0 . [all data]

Tan, Wilkins, et al., 1989
Tan, S.T.; Wilkins, A.L.; Holland, P.T.; McGhie, T.K., Extractives from New Zealand unifloral honeys. 2. Degraded carotenoids and other substances from heather honey, J. Agric. Food Chem., 1989, 37, 5, 1217-1221, https://doi.org/10.1021/jf00089a004 . [all data]

Peng, Ding, et al., 1988
Peng, C.T.; Ding, S.F.; Hua, R.L.; Yang, Z.C., Prediction of Retention Indexes I. Structure-Retention Index Relationship on Apolar Columns, J. Chromatogr., 1988, 436, 137-172, https://doi.org/10.1016/S0021-9673(00)94575-8 . [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]

Buchman, Cao, et al., 1984
Buchman, O.; Cao, G.-Y.; Peng, C.T., Structure assignment by retention index in gas-liquid radiochromatography of substituted cyclohexenes, J. Chromatogr., 1984, 312, 75-90, https://doi.org/10.1016/S0021-9673(01)92765-7 . [all data]

Varlet, Serot, et al., 2007
Varlet, V.; Serot, T.; Cardinal, M.; Knockaert, C.; Prost, C., Olfactometric Determination of the Most Potent Odor-Active Compounds in Salmon Muscle (Salmo salar) Smoked by Using Four Smoke Generation Techniques, J. Agric. Food Chem., 2007, 55, 11, 4518-4525, https://doi.org/10.1021/jf063468f . [all data]

Mjøs, Meier, et al., 2006
Mjøs, S.A.; Meier, S.; Boitsov, S., Alkylphenol retention indices, J. Chromatogr. A, 2006, 1123, 1, 98-105, https://doi.org/10.1016/j.chroma.2006.05.002 . [all data]

Varlet V., Knockaert C., et al., 2006
Varlet V.; Knockaert C.; Prost C.; Serot T., Comparison of odor-active volatile compounds of fresh and smoked salmon, J. Agric. Food Chem., 2006, 54, 9, 3391-3401, https://doi.org/10.1021/jf053001p . [all data]

Place, Imhof, et al., 2003
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Notes

Go To: Top, Condensed phase thermochemistry data, Henry's Law data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, References

• Symbols used in this document:
  

  Cp,solid	Constant pressure heat capacity of solid
  S°solid,1 bar	Entropy of solid at standard conditions (1 bar)
  d(ln(kH))/d(1/T)	Temperature dependence parameter for Henry's Law constant
  k°H	Henry's Law constant at 298.15K
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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