Acetophenone, 4'-hydroxy-

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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

Quantity Value Units Method Reference Comment
Tfus311.KN/ADauben and Collette, 1959Uncertainty assigned by TRC = 3. K; TRC
Tfus383.KN/ASimons, Randall, et al., 1939Uncertainty assigned by TRC = 2. K; TRC
Tfus379.65KN/ACoulthard, Marshall, et al., 1930Uncertainty assigned by TRC = 2. K; TRC

Reduced pressure boiling point

Tboil (K) Pressure (atm) Reference Comment
420.70.004Weast and Grasselli, 1989BS

Enthalpy of sublimation

ΔsubH (kcal/mol) Temperature (K) Method Reference Comment
22.9335.AStephenson and Malanowski, 1987Based on data from 320. to 349. K. See also Aihara, 1960.; AC

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Method Reference Comment
4.321382.8N/ABernardes, Piedade, et al., 2008AC
4.06381.3DSCChen, Tang, et al., 2005AC

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 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)

Quantity Value Units Method Reference Comment
Proton affinity (review)211.2kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity203.6kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.70 ± 0.03EIFoffani, Pignataro, et al., 1964RDSH

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C7H5O2+10.42CH3EIHowe and Williams, 1969RDSH
C7H5O2+9.84CH3EIBuchs, Rossetti, et al., 1964RDSH

De-protonation reactions

C8H7O2- + Hydrogen cation = Acetophenone, 4'-hydroxy-

By formula: C8H7O2- + H+ = C8H8O2

Quantity Value Units Method Reference Comment
Δr335.5 ± 2.1kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr328.6 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B

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

View large format table.

Column type Active phase Temperature (C) I Reference Comment
PackedOV-3160.1490.7Hassani and Meklati, 1992N2, Chromosorb G HP; Column length: 5. m

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

View large format table.

Column type Active phase I Reference Comment
CapillaryHP-5MS1442.Lalel, Singh, et al., 200360. 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

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-Wax1786.Shiratsuchi, Shimoda, et al., 199460. m/0.25 mm/0.25 μm, He, 2. K/min, 230. C @ 60. min; Tstart: 50. C

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

View large format table.

Column type Active phase I Reference Comment
CapillarySupelcowax-101790.Sing, Smadja, et al., 199260. 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
CapillaryZB-51447.Harrison and Priest, 200930. 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

View large format table.

Column type Active phase I Reference Comment
CapillaryBP-201779.Pontes, Marques, et al., 200730. m/0.25 mm/0.25 μm, He; Program: 50C(1min) => 2.5C/min => 100C => 2C/min => 180C => 15C/min => 220C
CapillaryCarbowax 20M1790.Vinogradov, 2004Program: not specified

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