3-Methoxyacetophenone
- Formula: C9H10O2
- Molecular weight: 150.1745
- IUPAC Standard InChI: InChI=1S/C9H10O2/c1-7(10)8-4-3-5-9(6-8)11-2/h3-6H,1-2H3
- IUPAC Standard InChIKey: BAYUSCHCCGXLAY-UHFFFAOYSA-N
- CAS Registry Number: 586-37-8
- 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-(3-methoxyphenyl)-; Acetophenone, 3'-methoxy-; 3-Acetylanisole; 1-Acetyl-3-methoxybenzene; m-Methoxyacetophenone; 3'-Methoxyacetophenone; Methyl 3-methoxyphenyl ketone; meta-Methoxyacetophenone; m-Acetanisole; Acetophenone, m-methoxy-; m-Metoxyacetophenone; 3-Methoxy-1-acetylbenzene; NSC 65593; m-Acetylanisole; 1-(3-methoxyphenyl)ethanone
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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 by: Robert L. Brown and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tboil | 513.2 | K | N/A | Weast and Grasselli, 1989 |
Reduced pressure boiling point
| Tboil (K) | Pressure (bar) | Reference |
|---|---|---|
| 398.7 | 0.016 | Weast and Grasselli, 1989 |
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 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
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Proton affinity (review) | 871.2 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
| Quantity | Value | Units | Method | Reference | Comment |
| Gas basicity | 839.3 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 8.53 ± 0.05 | EI | Pignataro, Foffani, et al., 1966 | RDSH |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C8H7O2+ | 10.7 ± 0.1 | CH3 | EI | Chin and Harrison, 1969 | RDSH |
De-protonation reactions
C9H9O2- + =
By formula: C9H9O2- + H+ = C9H10O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1509. ± 8.8 | kJ/mol | G+TS | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1481. ± 8.4 | kJ/mol | IMRE | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
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
Van Den Dool and Kratz RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | HP-5 | 1298. | Alonzo, Bosco, et al., 2000 | 30. m/0.20 mm/0.25 μm, He, 60. C @ 8. min, 4. K/min, 180. C @ 2. min |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-5 | 1295. | Basile, Senatore, et al., 2006 | 30. m/0.25 mm/0.25 μm; Program: 40C(5min) => 2C/min => 250C(15min) => 10C/min => 270C |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | HP-5 MS | 1321. | Jerkovic and Marijanovic, 2010 | 30. m/0.25 mm/0.25 μm, Helium, 70. C @ 2. min, 3. K/min, 200. C @ 18. min |
| Capillary | DB-5 | 1301. | Miyazawa, Nishiguchi, et al., 2005 | 30. m/0.25 mm/0.25 μm, He, 3. K/min; Tstart: 60. C; Tend: 240. C |
| Capillary | DB-1 | 1282. | Palá-Paúl, Velasco-Negueruela, et al., 2004 | 50. m/0.25 mm/0.25 μm, N2, 4. K/min; Tstart: 95. C; Tend: 240. C |
| Capillary | Cross-Linked Methylsilicone | 1277. | Velasco-Negueruela, Pérez-Alonso, et al., 2003 | 25. m/0.2 mm/0.33 μm, He, 4. K/min; Tstart: 70. C; Tend: 250. C |
Normal alkane RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | SE-30 | 1279. | Vinogradov, 2004 | Program: not specified |
Normal alkane RI, polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-Wax | 2148. | Gyawali and Kim, 2012 | 60. m/0.20 mm/0.25 μm, Helium; Program: 40 0C (3 min) 2 0C/min -> 150 0C 4 0C/min -> 220 0C (20 min) 5 0C/min -> 230 0C |
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]
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]
Pignataro, Foffani, et al., 1966
Pignataro, S.; Foffani, A.; Innorta, G.; Distefano, G.,
Molecular structural effects on the ionization potentials for metasubstituted aromatic compounds and for compounds of the type X-CH2-R,
Z. Physik. Chem. (Frankfurt), 1966, 49, 291. [all data]
Chin and Harrison, 1969
Chin, M.S.; Harrison, A.G.,
Substituent effects on ion abundances and energetics in substituted acetophenones,
Org. Mass Spectrom., 1969, 2, 1073. [all data]
Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr.,
The gas phase acidity scale from methanol to phenol,
J. Am. Chem. Soc., 1979, 101, 6047. [all data]
Alonzo, Bosco, et al., 2000
Alonzo, G.; Bosco, S.F.D.; Palazzolo, E.; Saiano, F.; Tusa, N.,
Citrus somatic hybrid leaf essential oil,
Flavour Fragr. J., 2000, 15, 4, 258-262, https://doi.org/10.1002/1099-1026(200007/08)15:4<258::AID-FFJ906>3.0.CO;2-F
. [all data]
Basile, Senatore, et al., 2006
Basile, A.; Senatore, F.; Gargano, R.; Sorbo, S.; Del Pezzo, M.; Lavitola, A.; Ritieni, A.; Bruno, M.; Spatuzzi, D.; Rigano, D.; Vuotto, M.L.,
Antibacterial and antioxidant activities in Sideritis italica (Miller) Greuter et Burdet essential oils,
J. Ethnopharmacol., 2006, 107, 2, 240-248, https://doi.org/10.1016/j.jep.2006.03.019
. [all data]
Jerkovic and Marijanovic, 2010
Jerkovic, I.; Marijanovic, Z.,
Oak (Quercus frainetto Ten.) honeydaw honey - approach to screening of volatile organic composition and antioxidant capacity (DPPH and FRAP assay),
Molecules, 2010, 15, 5, 3744-3756, https://doi.org/10.3390/molecules15053744
. [all data]
Miyazawa, Nishiguchi, et al., 2005
Miyazawa, M.; Nishiguchi, T.; Yamafuji, C.,
Volatile components of the leaves of Brassica rapa L. var. perviridis Bailey,
Flavour Fragr. J., 2005, 20, 2, 158-160, https://doi.org/10.1002/ffj.1335
. [all data]
Palá-Paúl, Velasco-Negueruela, et al., 2004
Palá-Paúl, J.; Velasco-Negueruela, A.; Pérez-Alonso, M.J.; Maqueda, J.; Sanz, J.,
Volatile oil constituents from different parts of Cachrys trifida L.,
J. Essent. Oil Res., 2004, 16, 4, 347-349, https://doi.org/10.1080/10412905.2004.9698738
. [all data]
Velasco-Negueruela, Pérez-Alonso, et al., 2003
Velasco-Negueruela, A.; Pérez-Alonso, M.J.; Pérez de Paz, P.L.; Palá-Paúl, J.; Sanz, J.,
Analysis by gas chromatography-mass spectrometry of the essential oil from the aerial parts of Pimpinella junoniae Ceb. Ort., gathered in La Gomera, Canary Islands, Spain,
J. Chromatogr. A, 2003, 1011, 1-2, 241-244, https://doi.org/10.1016/S0021-9673(03)01082-3
. [all data]
Vinogradov, 2004
Vinogradov, B.A.,
Production, composition, properties and application of essential oils, 2004, retrieved from http://viness.narod.ru. [all data]
Gyawali and Kim, 2012
Gyawali, R.; Kim, K.-S.,
Bioactive volatile compounds of three medicinal plants from Nepal,
Kathmandu Univ. J. Sci., Engineering and Technol., 2012, 8, 1, 51-62. [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 ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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