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 Copy

  
• IUPAC Standard InChIKey: TXFPEBPIARQUIG-UHFFFAOYSA-N Copy
• 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
  The 3d structure may be viewed using Java or Javascript.
• 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
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Phase change data
  • Gas phase ion energetics data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Phase change 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:
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

Reduced pressure boiling point

Enthalpy of sublimation

Enthalpy of fusion

Gas phase ion energetics 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C₈H₈O₂⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₈H₇O₂^- +  =

By formula: C₈H₇O₂^- + H⁺ = C₈H₈O₂

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

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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, temperature ramp

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Normal alkane RI, polar column, custom temperature program

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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.

Dauben and Collette, 1959
Dauben, W.G.; Collette, J.W., An Abnormal Reaction of an Organocadmium Reagent: para-Acylation of m-Methoxythenylcadmium Reagent, J. Am. Chem. Soc., 1959, 81, 967-72. [all data]

Simons, Randall, et al., 1939
Simons, J.H.; Randall, D.I.; Archer, S., Hydrogen Fluoride as A Condensing Agent VI. The Acylaction of Aromatic Compounds, J. Am. Chem. Soc., 1939, 61, 1795. [all data]

Coulthard, Marshall, et al., 1930
Coulthard, C.E.; Marshall, J.; Pyman, F.L., The Variation of Phenol Coefficients in a Homologous Series of Phenols, J. Chem. Soc., 1930, 1930, 280. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [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]

Bernardes, Piedade, et al., 2008
Bernardes, Carlos E.S.; Piedade, M. Fátima M.; Piedade, Manuel E. Minas da, Polymorphism in 4´-Hydroxyacetophenone: Structure and Energetics, Crystal Growth & Design, 2008, 8, 7, 2419-2430, https://doi.org/10.1021/cg7012792 . [all data]

Chen, Tang, et al., 2005
Chen, Yan-Ping; Tang, Muoi; Kuo, Ju-Chia, Solid--liquid equilibria for binary mixtures of N-phenylacetamide with 4-aminoacetophenone, 3-hydroxyacetophenone and 4-hydroxyacetophenone, Fluid Phase Equilibria, 2005, 232, 1-2, 182-188, https://doi.org/10.1016/j.fluid.2005.03.023 . [all data]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Foffani, Pignataro, et al., 1964
Foffani, A.; Pignataro, S.; Cantone, B.; Grasso, F., Ionization potentials and substituent effects for aromatic carbonyl compounds, Z. Physik. Chem. (Frankfurt), 1964, 42, 221. [all data]

Howe and Williams, 1969
Howe, I.; Williams, D.H., Calculation and qualitative predictions of mass spectra. Mono- and paradisubstituted benzenes, J. Am. Chem. Soc., 1969, 91, 7137. [all data]

Buchs, Rossetti, et al., 1964
Buchs, A.; Rossetti, G.P.; Susz, B.P., Etude, en fonction de la constante σp de Hammett, du spectre de masse d'acetophenones p-substituees, Helv. Chim. Acta, 1964, 47, 1563. [all data]

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]

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

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

• Symbols used in this document:
  

  AE	Appearance energy
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔfusH	Enthalpy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔsubH	Enthalpy of sublimation

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