Ethanone, 1-(2-hydroxyphenyl)-
- Formula: C8H8O2
- Molecular weight: 136.1479
- IUPAC Standard InChIKey: JECYUBVRTQDVAT-UHFFFAOYSA-N
- CAS Registry Number: 118-93-4
- 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: Acetophenone, 2'-hydroxy-; o-Acetylphenol; o-Hydroxyacetophenone; o-Hydroxyphenyl methyl ketone; 2-Acetylphenol; 2'-Hydroxyacetophenone; 1-(2-Hydroxyphenyl)ethanone; Acetophenone, o-hydroxy-; USAF KE-20; 2-Hydroxyacetylbenzene; 2-Hydroxyphenyl methyl ketone; Methyl 2-hydroxyphenyl ketone; NSC 16933
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Phase change data
Go To: Top, Gas phase ion energetics data, Gas Chromatography, References, Notes
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 |
---|---|---|---|---|---|
Tboil | 491.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 301.15 | K | N/A | Coulthard, Marshall, et al., 1930 | Uncertainty assigned by TRC = 1. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 13.9 ± 0.07 | kcal/mol | C | Bernardes and Minas da Piedade, 2008 | AC |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
486.2 | 0.943 | Aldrich Chemical Company Inc., 1990 | BS |
379.2 | 0.022 | Weast and Grasselli, 1989 | BS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
13.9 | 384. | A | Stephenson and Malanowski, 1987 | Based on data from 369. to 491. K.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
3.11 | 278.5 | DSC | Bernardes and Minas da Piedade, 2008 | AC |
Gas phase ion energetics data
Go To: Top, Phase change data, Gas Chromatography, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: John E. Bartmess
View reactions leading to C8H8O2+ (ion structure unspecified)
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
0.850 ± 0.048 | IMRE | Fukuda and McIver, 1985 | ΔGea(355 K) = -20.7 kcal/mol; ΔSea = 3.0, est. from data in Kebarle and Chowdhury, 1987 |
Gas Chromatography
Go To: Top, Phase change data, Gas phase ion energetics data, References, Notes
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
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | OV-101 | 120. | 1135.6 | Righezza, Hassani, et al., 1996 | N2, Chromosorb G HP; Column length: 5. m |
Packed | OV-101 | 130. | 1139.1 | Righezza, Hassani, et al., 1996 | N2, Chromosorb G HP; Column length: 5. m |
Packed | OV-101 | 140. | 1152.5 | Righezza, Hassani, et al., 1996 | N2, Chromosorb G HP; Column length: 5. m |
Packed | OV-101 | 160. | 1162.7 | Hassani and Meklati, 1992 | N2, Chromosorb G HP; Column length: 5. m |
Packed | SE-30 | 190. | 1158. | Haken and Abraham, 1988 | Column length: 3.7 m |
Kovats' RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | OV-101 | 1140. | Yamaguchi and Shibamoto, 1979 | N2, 2. K/min; Column length: 70. m; Column diameter: 0.28 mm; Tstart: 80. C; Tend: 200. C |
Capillary | OV-101 | 1144. | Yamaguchi and Shibamoto, 1979 | N2, 2. K/min; Column length: 70. m; Column diameter: 0.28 mm; Tstart: 80. C; Tend: 200. C |
Kovats' RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Carbowax 20M | 1709. | Yamaguchi and Shibamoto, 1979 | N2, 2. K/min; Column length: 50. m; Column diameter: 0.28 mm; Tstart: 80. C; Tend: 200. C |
Capillary | Carbowax 20M | 1714. | Yamaguchi and Shibamoto, 1979 | N2, 2. K/min; Column length: 50. m; Column diameter: 0.28 mm; Tstart: 80. C; Tend: 200. C |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-1 | 1124. | Xu, Tang, et al., 2010 | 30. m/0.25 mm/0.25 μm, Helium, 50. C @ 2. min, 4. K/min, 220. C @ 2. min |
Capillary | HP-5 MS | 1167. | Radulovic, Blagojevic, et al., 2009 | 30. m/0.25 mm/0.25 μm, Helium, 5. K/min, 290. C @ 10. min; Tstart: 70. C |
Capillary | HP-101 | 1165. | Mastelic, Jerkovic, et al., 2006 | 25. m/0.2 mm/0.2 μm, He, 70. C @ 2. min, 3. K/min, 200. C @ 15. min |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-1 | 1140. | Xu, Tang, et al., 2010 | 30. m/0.25 mm/0.25 μm, Helium; Program: not specified |
Capillary | OV-101 | 1136. | Ebrahimi and Hadjmohammadi, 2006 | Program: not specified |
Normal alkane RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-20M | 1747. | Mastelic, Jerkovic, et al., 2006 | 50. m/0.2 mm/0.2 μm, He, 70. C @ 4. min, 4. K/min, 180. C @ 15. min |
Capillary | Carbowax 20M | 1709. | Yamaguchi and Shibamoto, 1980 | N2, 1. K/min; Column length: 50. m; Column diameter: 0.28 mm; Tstart: 80. C; Tend: 170. C |
Capillary | Carbowax 20M | 1714. | Yamaguchi and Shibamoto, 1980 | N2, 1. K/min; Column length: 50. m; Column diameter: 0.28 mm; Tstart: 80. C; Tend: 170. C |
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.
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]
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]
Bernardes and Minas da Piedade, 2008
Bernardes, Carlos E.S.; Minas da Piedade, Manuel E.,
Energetics of the O-H Bond and of Intramolecular Hydrogen Bonding in HOC 6 H 4 C(O)Y (Y = H, CH 3 , CH 2 CH«58875»CH 2 , C«58876»CH, CH 2 F, NH 2 , NHCH 3 , NO 2 , OH, OCH 3 , OCN, CN, F, Cl, SH, and SCH 3 ) Compounds,
J. Phys. Chem. A, 2008, 112, 40, 10029-10039, https://doi.org/10.1021/jp804455u
. [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]
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]
Fukuda and McIver, 1985
Fukuda, E.K.; McIver, R.T., Jr.,
Relative electron affinities of substituted benzophenones, nitrobenzenes, and quinones. [Anchored to EA(SO2) from 74CEL/BEN],
J. Am. Chem. Soc., 1985, 107, 2291. [all data]
Kebarle and Chowdhury, 1987
Kebarle, P.; Chowdhury, S.,
Electron affinities and electron transfer reactions,
Chem. Rev., 1987, 87, 513. [all data]
Righezza, Hassani, et al., 1996
Righezza, M.; Hassani, A.; Meklati, B.Y.; Chrétien, J.R.,
Quantitative structure-retention relationships (QSRR) of congeneric aromatics series studied on phenyl OV phases in gas chromatography,
J. Chromatogr. A, 1996, 723, 1, 77-91, https://doi.org/10.1016/0021-9673(95)00816-0
. [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]
Haken and Abraham, 1988
Haken, J.K.; Abraham, F.,
Demonstration of intermolecular and intramolecular hydrogen bonding by gas chromatographic measurements,
J. Chromatogr., 1988, 440, 329-332, https://doi.org/10.1016/S0021-9673(00)94536-9
. [all data]
Yamaguchi and Shibamoto, 1979
Yamaguchi, K.; Shibamoto, T.,
Volatile constituents of Castanopsis flower,
J. Agric. Food Chem., 1979, 27, 4, 847-850, https://doi.org/10.1021/jf60224a025
. [all data]
Xu, Tang, et al., 2010
Xu, X.; Tang, Z.; Liang, Y.,
Comparative analysis of plant essential oils by GC-MS coupled with integrated chemometric resolution methods,
Anal. Methods, 2010, 2, 4, 359-367, https://doi.org/10.1039/b9ay00213h
. [all data]
Radulovic, Blagojevic, et al., 2009
Radulovic, N.S.; Blagojevic, P.D.; Palic, R.M.; Zlatkovic, B.K.; Stevanovic, B.M.,
Volatiles from vegetative organs of the paleoendemic resurrection plants Ramonda serbica Panc. and Ramonda nathaliae Panc. at Petrov,
J. Serb. Chem. Soc., 2009, 74, 1, 35-44, https://doi.org/10.2298/JSC0901035R
. [all data]
Mastelic, Jerkovic, et al., 2006
Mastelic, J.; Jerkovic, I.; Mesic, M.,
Volatile constituents from flowers, leaves, bark and wood of Prunus mahaleb L.,
Flavour Fragr. J., 2006, 21, 2, 306-313, https://doi.org/10.1002/ffj.1596
. [all data]
Ebrahimi and Hadjmohammadi, 2006
Ebrahimi, P.; Hadjmohammadi, M.R.,
Simultaneous modeling of the Kovats retention indices on phenyl OV stationary phases with different polarity using MLR and ANN,
QSAR Comb. Sci., 2006, 25, 10, 836-845, https://doi.org/10.1002/qsar.200530145
. [all data]
Yamaguchi and Shibamoto, 1980
Yamaguchi, K.; Shibamoto, T.,
Volatile constituents of the chestnut flower,
J. Agric. Food Chem., 1980, 28, 1, 82-84, https://doi.org/10.1021/jf60227a021
. [all data]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
EA Electron affinity Tboil Boiling point Tfus Fusion (melting) point ΔfusH Enthalpy of fusion ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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