4-Acetylanisole
- Formula: C9H10O2
- Molecular weight: 150.1745
- IUPAC Standard InChIKey: NTPLXRHDUXRPNE-UHFFFAOYSA-N
- CAS Registry Number: 100-06-1
- 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, 4'-methoxy-; Ethanone, 1-(4-methoxyphenyl)-; p-Acetylanisole; p-Methoxyacetophenone; p-Methoxyphenyl methyl ketone; Linarodin; Novatone; Vananote; 4-Methoxyphenyl methyl ketone; 4'-Methoxyacetophenone; 4-Methoxyacetophenone; para-Methoxyacetophenone; Acetanisole; Methyl p-methoxyphenyl ketone; 4-Methoxyacetofenon; Acetophenone, p-methoxy-; p-Metoxyacetophenone; Methyl 4-methoxyphenyl ketone; NSC 209523; 4-Methoxyacetophenon; Anise ketone; 1-(4-Methoxyphenyl)ethanone; para-Methoxyacetophenone (acetanisole)
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Gas phase ion energetics data
Go To: Top, IR Spectrum, Mass spectrum (electron ionization), 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:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 895.6 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 863.7 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.2 ± 0.1 | PE | Egdell, Green, et al., 1975 | LLK |
8.62 ± 0.05 | EI | Foffani, Pignataro, et al., 1964 | RDSH |
8.52 | PE | Distefano, Granozzi, et al., 1987 | Vertical value; LBLHLM |
8.65 | PE | Gal, Geribaldi, et al., 1985 | Vertical value; LBLHLM |
8.65 | PE | Koenig, Wielesek, et al., 1977 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C8H7O2+ | 10.69 ± 0.04 | CH3 | EI | Helal and Zahran, 1978 | LLK |
C8H7O2+ | 10.2 ± 0.1 | CH3 | EI | Chin and Harrison, 1969 | RDSH |
IR Spectrum
Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References, Notes
Data compiled by: Coblentz Society, Inc.
- LIQUID; Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY; 4 cm-1 resolution
- SOLUTION (10% CCl4 FOR 3800-1330, 10% CS2 FOR 1330-400 CM-1) $$ SEE SPECTRUM NO. 3706 FOR "LIQUID (NEAT)" AND SPECTRUM NO. 8646 FOR "10% SOLUTION" STATES; DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY; 2 cm-1 resolution
- SOLUTION (10% CCl4 FOR 3800-1335, 10% CS2 FOR 1335-400 CM-1) $$ SEE SEPCTRUM NO. 3706 FOR "LIQUID (NEAT)" AND SPECTRUM NO. 8647 FOR "2% SOLUTION" STATES; DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY; 2 cm-1 resolution
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Mass spectrum (electron ionization)
Go To: Top, Gas phase ion energetics data, IR Spectrum, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | D.HENNEBERG, MAX-PLANCK INSTITUTE, MULHEIM, WEST GERMANY |
NIST MS number | 63846 |
Gas Chromatography
Go To: Top, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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 |
---|---|---|---|---|---|
Capillary | SE-30 | 100. | 1337.0 | Tudor, 1997 | 40. m/0.35 mm/0.35 μm |
Packed | OV-101 | 120. | 1310.9 | Righezza, Hassani, et al., 1996 | N2, Chromosorb G HP; Column length: 5. m |
Packed | OV-101 | 130. | 1314.3 | Righezza, Hassani, et al., 1996 | N2, Chromosorb G HP; Column length: 5. m |
Packed | OV-101 | 140. | 1325.8 | Righezza, Hassani, et al., 1996 | N2, Chromosorb G HP; Column length: 5. m |
Packed | OV-3 | 120. | 1392.4 | Righezza, Hassani, et al., 1996 | N2, Chromosorb G HP; Column length: 5. m |
Packed | OV-3 | 130. | 1394. | Righezza, Hassani, et al., 1996 | N2, Chromosorb G HP; Column length: 5. m |
Packed | OV-101 | 160. | 1333.4 | Hassani and Meklati, 1992 | N2, Chromosorb G HP; Column length: 5. m |
Kovats' RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Carbowax 20M | 2144. | Nishimura, Yamaguchi, et al., 1989 | 2. K/min; Column length: 50. m; Column diameter: 0.22 mm; Tstart: 80. C; Tend: 200. C |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5MS | 1345. | Pino, Mesa, et al., 2005 | 30. m/0.25 mm/0.25 μm, He, 60. C @ 2. min, 4. K/min, 250. C @ 20. min |
Capillary | HP-5 | 1348. | Aligiannis, Kalpoutzakis, et al., 2001 | 30. m/0.25 mm/0.25 μm, He, 60. C @ 5. min, 3. K/min; Tend: 280. C |
Capillary | HP-5 | 1369. | David, Scanlan, et al., 2000 | 50. m/0.32 mm/1.05 μm, He, 2. K/min; Tstart: 50. C; Tend: 290. C |
Capillary | OV-1 | 1337. | Bicchi, Fresia, et al., 1997 | 25. m/0.25 mm/0.3 μm, H2, 50. C @ 1. min, 3. K/min, 200. C @ 20. min |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 1338. | Basile, Senatore, et al., 2006 | 30. m/0.25 mm/0.25 μm; Program: 40C(5min) => 2C/min => 250C(15min) => 10C/min => 270C |
Van Den Dool and Kratz RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-Innowax | 2120. | Adamiec, Cejpek, et al., 2001 | 30. m/0.25 mm/0.25 μm, N2, 5. K/min; Tstart: 60. C; Tend: 220. C |
Van Den Dool and Kratz RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | CP-Wax 52CB | 2144. | Romeo, Ziino, et al., 2007 | 60. m/0.25 mm/0.25 μm, He; Program: 45C(5min) => 10C/min => 80C => 2C/min => 240C |
Normal alkane RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | DB-5 | 25. | 1348. | Hemmateenejad, Jawadnia, et al., 2007 |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5 MS | 1360. | Jerkovic, Tuberso, et al., 2010 | 30. m/0.25 mm/0.25 μm, Helium, 70. C @ 2. min, 3. K/min, 200. C @ 18. min |
Capillary | DB-1-MS | 1303. | Takeoka, Hobbs, et al., 2010 | 60. m/0.25 mm/0.25 μm, Helium, 30. C @ 4. min, 2. K/min, 200. C @ 35. min |
Capillary | Elite-5MS | 1355. | Tava, Pecetti, et al., 2007 | 30. m/0.32 mm/0.5 μm, He, 40. C @ 5. min, 4. K/min, 280. C @ 10. min |
Capillary | HP-5 MS | 1350. | Vagionas, Graikou, et al., 2007 | 30. m/0.25 mm/0.25 μm, Helium, 3. K/min; Tstart: 60. C; Tend: 280. C |
Capillary | DB-5 | 1304. | Senatore, Landolfi, et al., 2006 | 30. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 2. K/min, 260. C @ 20. min |
Capillary | DB-5 | 1345. | Tellez, Khan, et al., 2004 | 30. m/0.25 mm/0.25 μm, He, 3. K/min; Tstart: 60. C; Tend: 240. C |
Capillary | HP-5MS | 1348. | Afsharypuor and Jahromy, 2003 | 30. m/0.25 mm/0.25 μm, He, 4. K/min; Tstart: 60. C; Tend: 275. C |
Capillary | DB-5 | 1303. | Senatore and Bruno, 2003 | 30. m/0.25 mm/0.25 μm, 40. C @ 5. min, 2. K/min; Tend: 260. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-1-MS | 1302. | Takeoka, Hobbs, et al., 2010 | 60. m/0.25 mm/0.25 μm, Helium; Program: not specified |
Capillary | OV-101 | 1311. | Ebrahimi and Hadjmohammadi, 2006 | Program: not specified |
Capillary | SE-30 | 1327. | Vinogradov, 2004 | Program: not specified |
Capillary | HP-5 | 1369.0 | David, Scanlan, et al., 2002 | 50. m/0.32 mm/1.05 μm, He; Program: not specified |
Capillary | DB-1 | 1310. | Marlatt, Ho, et al., 1992 | 30. m/0.25 mm/0.25 μm; Program: not specified |
Capillary | SE-54 | 1350. | Fagan, Kepner, et al., 1982 | He; Column length: 35. m; Column diameter: 0.25 mm; Program: not specified |
Capillary | SE-54 | 1355. | Fagan, Kepner, et al., 1982 | He; Column length: 35. m; Column diameter: 0.25 mm; Program: not specified |
Normal alkane RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | TC-Wax | 2150. | Shuichi, Masazumi, et al., 1996 | 80. C @ 5. min, 3. K/min; Column length: 60. m; Column diameter: 0.25 mm; Tend: 240. C |
Capillary | TC-Wax | 2164. | Shuichi, Masazumi, et al., 1996 | 80. C @ 5. min, 3. K/min; Column length: 60. m; Column diameter: 0.25 mm; Tend: 240. C |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | SOLGel-Wax | 2116. | Shu and Shen, 2008 | 30. m/0.53 mm/0.50 μm, Helium; Program: 40 0C 7 0C/min -> 180 0C 10 0C/min -> 240 0C (10 min) |
Capillary | SOLGel-Wax | 2115. | Shu and Shen, 2008 | 30. m/0.53 mm/0.50 μm, Helium; Program: not specified |
Capillary | Carbowax 20M | 2115. | Vinogradov, 2004 | Program: not specified |
References
Go To: Top, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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
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Egdell, Green, et al., 1975
Egdell, R.; Green, J.C.; Rao, C.N.R.,
Photoelectron spectra of substituted benzenes,
Chem. Phys. Lett., 1975, 33, 600. [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]
Distefano, Granozzi, et al., 1987
Distefano, G.; Granozzi, G.; Olivato, P.R.; Guerrero, S.A.,
Hyperconjugative interactions in halogen-substituted carbonyls: Ultraviolet photoelectron spectroscopy of w-halogenoacetophenones,
J. Chem. Soc. Perkin Trans. 2, 1987, 1459. [all data]
Gal, Geribaldi, et al., 1985
Gal, J.-F.; Geribaldi, S.; Pfister-Guillouzo, G.; Morris, D.G.,
Basicity of the carbonyl group. Part 12. Correlations between ionization potentials and lewis basicities in aromatic carbonyl compounds,
J. Chem. Soc. Perkin Trans. 2, 1985, 103. [all data]
Koenig, Wielesek, et al., 1977
Koenig, T.; Wielesek, R.; Miller, L.L.; So, Y.-H.,
Correlation of electrochemical reactivity and photoelectron spectra of aromatic ketones,
J. Am. Chem. Soc., 1977, 99, 7061. [all data]
Helal and Zahran, 1978
Helal, A.I.; Zahran, N.F.,
Kinetic shift in some para-substituted acetophenones,
Org. Mass Spectrom., 1978, 13, 549. [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]
Tudor, 1997
Tudor, E.,
Temperature dependence of the retention index for perfumery compounds on a SE-30 glass capillary column. I. Linear equations,
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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
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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
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Nishimura, Yamaguchi, et al., 1989
Nishimura, O.; Yamaguchi, K.; Mihara, S.; Shibamoto, T.,
Volatile Constituents of Guava Fruits (Psidium guajava L.) and Canned Puree,
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Pino, Mesa, et al., 2005
Pino, J.A.; Mesa, J.; Muñoz, Y.; Martí, M.P.; Marbot, R.,
Volatile components from mango (Mangifera indica L.) cultivars,
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Aligiannis, Kalpoutzakis, et al., 2001
Aligiannis, N.; Kalpoutzakis, E.; Chinou, I.B.; Mitaku, S.; Gikas, E.; Tsarbopoulos, A.,
Composition and antimicrobial activity of the essential oils of five taxa of Sideritis from Greece,
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David, Scanlan, et al., 2000
David, F.; Scanlan, F.; Sandra, P.,
Retention time locking in flavor analysis, Proceedings 23rd ISCC; CD-ROM, 2000, retrieved from http://www.richrom.com/assets/CD23PDF. [all data]
Bicchi, Fresia, et al., 1997
Bicchi, C.; Fresia, M.; Rubiolo, P.; Monti, D.; Franz, C.; Goehler, I.,
Constituents of Tagetes lucida Cav. ssp. lucida essential oil,
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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,
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Adamiec, Cejpek, et al., 2001
Adamiec, J.; Cejpek, K.; Rossner, J.; Velisek, J.,
Novel Strecker degradation products of tyrosine and dihydroxyphenylalanine,
Czech. J. Food. Sci., 2001, 19, 1, 13-18. [all data]
Romeo, Ziino, et al., 2007
Romeo, V.; Ziino, M.; Giuffrrida, D.; Condurso, C.; Verzera, A.,
Flavour profile of capers (Capparis spinosa L.) from the Eolian Archipelago by HS-SPME/GC?MS,
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Hemmateenejad, Jawadnia, et al., 2007
Hemmateenejad, B.; Jawadnia, K.; Elyasi, M.,
Quantitative structure - retention relationship for the Kovats retention indices of a large set of terpenes: a comdined data splitting-feature selection strategy,
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Jerkovic, Tuberso, et al., 2010
Jerkovic, I.; Tuberso, C.I.G.; Gugic, M.; Bubalo, D.,
Composition of Sulla (Hedysarum coronarium L.) honey solvent extractives determined by GC/MS: norisoprenoids and other volatile organic compounds,
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Takeoka, Hobbs, et al., 2010
Takeoka, G.R.; Hobbs, C.; Byeoung-Soo, P.,
Volatile constituents of the aerial parts of Salvia apiana Jepson,
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Tava, Pecetti, et al., 2007
Tava, A.; Pecetti, L.; Ricci, M.; Pagnotta, M.A.; Russi, L.,
Volatile compounds from leaves and flowers of Bituminaria bituminosa (L.) Stirt. (Fabaceae) from Italy,
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Vagionas, Graikou, et al., 2007
Vagionas, K.; Graikou, K.; Ngassapa, O.; Runyoro, D.; Chinou, I.,
Composition and antimicrobial activity of the essential oils of three Satureja species growing in Tansania,
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Senatore, Landolfi, et al., 2006
Senatore, F.; Landolfi, S.; Celik, S.; Bruno, M.,
Volatile components of Centaurea calcitrapa L. and Centaurea sphaerocephala L. ssp. sphaerocephala, two Asteraceae growing wild in Sicily,
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Tellez, Khan, et al., 2004
Tellez, M.R.; Khan, I.A.; Schaneberg, B.T.; Crockett, S.L.; Rimando, A.M.; Kobaisy, M.,
Steam distillation-solid-phase microextraction for the detection of Ephedra sinica in herbal preparations,
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Afsharypuor and Jahromy, 2003
Afsharypuor, S.; Jahromy, M.M.,
Constituents of the essential oil from Tanacetum lingulatum (Boiss.) Bornm.,
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Senatore and Bruno, 2003
Senatore, F.; Bruno, M.,
Composition of the essential oil of Pallenis spinosa (L.) Cass. (Asteraceae),
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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,
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Vinogradov, 2004
Vinogradov, B.A.,
Production, composition, properties and application of essential oils, 2004, retrieved from http://viness.narod.ru. [all data]
David, Scanlan, et al., 2002
David, F.; Scanlan, F.; Sandra, P.; Szelewski, M.,
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Marlatt, Ho, et al., 1992
Marlatt, C.; Ho, C.-T.; Chien, M.,
Studies of aroma constituents bound as glycosides in tomato,
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Fagan, Kepner, et al., 1982
Fagan, G.L.; Kepner, R.E.; Webb, A.D.,
Additional volatile components of Palomino film sherry,
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Shuichi, Masazumi, et al., 1996
Shuichi, H.; Masazumi, N.; Hiromu, K.; Kiyoshi, F.,
Comparison of volatile compounds berween the crude drugs, Onji-tsutsu and Onji-niki,
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Shu and Shen, 2008
Shu, N.; Shen, H.,
Aroma-impact compounds in Lysimachia foenum-graecum extracts,
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Notes
Go To: Top, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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