Acetophenone, 4'-hydroxy-

Formula: C₈H₈O₂
Molecular weight: 136.1479
IUPAC Standard InChI: InChI=1S/C8H8O2/c1-6(9)7-2-4-8(10)5-3-7/h2-5,10H,1H3
IUPAC Standard InChIKey: TXFPEBPIARQUIG-UHFFFAOYSA-N
CAS Registry Number: 99-93-4
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
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Other names: Ethanone, 1-(4-hydroxyphenyl)-; p-Hydroxyacetophenone; p-Hydroxyphenyl methyl ketone; p-Oxyacetophenone; Methyl p-hydroxyphenyl ketone; Phenol, p-acetyl-; Piceol; 1-(4-Hydroxyphenyl)ethanone; 4'-Hydroxyacetophenone; para-Hydroxyacetophenone; 4-Hydroxyacetophenone; Acetophenone, p-hydroxy-; Hydroxyacetophenone, para; USAF KF-15; p-Acetylphenol; 4-Acetylphenol; 4-Hydroksyacetofenol; NSC 3698
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Reaction thermochemistry data

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Data compiled by: John E. Bartmess

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Individual Reactions

C₈H₇O₂^- + = Acetophenone, 4'-hydroxy-

By formula: C₈H₇O₂^- + H⁺ = C₈H₈O₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	335.5 ± 2.1	kcal/mol	G+TS	Fujio, McIver, et al., 1981	gas phase; value altered from reference due to change in acidity scale
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	328.6 ± 2.0	kcal/mol	IMRE	Fujio, McIver, et al., 1981	gas phase; value altered from reference due to change in acidity scale

+ Acetophenone, 4'-hydroxy- = ( • )

By formula: Br^- + C₈H₈O₂ = (Br^- • C₈H₈O₂)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	25.1 ± 1.8	kcal/mol	IMRE	Paul and Kebarle, 1990	gas phase; ΔGaff at 423 K
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	15.4 ± 1.0	kcal/mol	IMRE	Paul and Kebarle, 1990	gas phase; ΔGaff at 423 K

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

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
Packed	OV-3	160.	1490.7	Hassani and Meklati, 1992	N2, Chromosorb G HP; Column length: 5. m

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

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Column type	Active phase	I	Reference	Comment
Capillary	HP-5MS	1442.	Lalel, Singh, et al., 2003	60. m/0.25 mm/0.25 μm, He, 40. C @ 1. min, 3. K/min, 310. C @ 20. min

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

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Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	1786.	Shiratsuchi, Shimoda, et al., 1994	60. m/0.25 mm/0.25 μm, He, 2. K/min, 230. C @ 60. min; T_start: 50. C

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

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Column type	Active phase	I	Reference	Comment
Capillary	Supelcowax-10	1790.	Sing, Smadja, et al., 1992	60. m/0.25 mm/0.25 μm, He; Program: 20C(0.5min) => 60C => 4C/min => 250C

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	ZB-5	1447.	Harrison and Priest, 2009	30. m/0.25 mm/0.25 μm, Helium, 40. C @ 1. min, 6. K/min, 280. C @ 9. min

Normal alkane RI, polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	BP-20	1779.	Pontes, Marques, et al., 2007	30. m/0.25 mm/0.25 μm, He; Program: 50C(1min) => 2.5C/min => 100C => 2C/min => 180C => 15C/min => 220C
Capillary	Carbowax 20M	1790.	Vinogradov, 2004	Program: not specified

References

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Fujio, McIver, et al., 1981
Fujio, M.; McIver, R.T., Jr.; Taft, R.W., Effects on the acidities of phenols from specific substituent-solvent interactions. Inherent substituent parameters from gas phase acidities, J. Am. Chem. Soc., 1981, 103, 4017. [all data]

Paul and Kebarle, 1990
Paul, G.J.C.; Kebarle, P., Stabilities in the Gas Phase of the Hydrogen Bonded Complexes, YC6H4OH-X-, of Substituted Phenols, YC6H4OH, with the Halide Anions X-(Cl-, Br-), Can. J. Chem., 1990, 68, 11, 2070, https://doi.org/10.1139/v90-316 . [all data]

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]

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]

Shiratsuchi, Shimoda, et al., 1994
Shiratsuchi, H.; Shimoda, M.; Imayoshi, K.; Noda, K.; Osajima, Y., Volatile flavor compounds in spray-dried skim milk powder, J. Agric. Food Chem., 1994, 42, 4, 984-988, https://doi.org/10.1021/jf00040a028 . [all data]

Sing, Smadja, et al., 1992
Sing, A.S.C.; Smadja, J.; Brevard, H.; Maignial, L.; Chaintreau, A.; Marion, J.-P., Volatile constituents of faham (Jumellea fragrans (Thou.) Schltr.), J. Agric. Food Chem., 1992, 40, 4, 642-646, https://doi.org/10.1021/jf00016a024 . [all data]

Harrison and Priest, 2009
Harrison, B.M.; Priest, F.G., Composition of peaks used in the preparation of malt for Scotch Whisky production - influence of geographical source and extraction depth, J. Agric. Food Chem., 2009, 57, 6, 2385-2391, https://doi.org/10.1021/jf803556y . [all data]

Pontes, Marques, et al., 2007
Pontes, M.; Marques, J.C.; Camara, J.S., Screening of volatile composition from Portuguese multifloral honeys using headspace solid-phase microextraction-gas chromatography-quadrupole mass spectrometry, Talanta, 2007, 74, 1, 91-103, https://doi.org/10.1016/j.talanta.2007.05.037 . [all data]

Vinogradov, 2004
Vinogradov, B.A., Production, composition, properties and application of essential oils, 2004, retrieved from http://viness.narod.ru. [all data]

Notes

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Symbols used in this document:

Δ_rG° Free energy of reaction at standard conditions

Δ_rH° Enthalpy of reaction at standard conditions
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions