Anisole
- Formula: C7H8O
- Molecular weight: 108.1378
- IUPAC Standard InChIKey: RDOXTESZEPMUJZ-UHFFFAOYSA-N
- CAS Registry Number: 100-66-3
- 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: Benzene, methoxy-; Anizol; Methoxybenzene; Methyl phenyl ether; Phenyl methyl ether; Ether, methyl phenyl-; UN 2222; Phenoxymethane; Anisol; NSC 7920
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Gas phase ion energetics data
Go To: Top, 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
L - Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
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
View reactions leading to C7H8O+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 8.20 ± 0.05 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 200.7 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 192.9 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.25 ± 0.03 | PI | Ponomarev, Arapov, et al., 1986 | LBLHLM |
~8.10 | PE | Klasinc, Kovac, et al., 1983 | LBLHLM |
8.24 | PE | Behan, Johnstone, et al., 1976 | LLK |
8.6 | EI | McLafferty, Bente, et al., 1973 | LLK |
8.20 ± 0.02 | PE | Maier and Turner, 1973 | LLK |
8.37 | CTS | Kobayashi, Kobayashi, et al., 1973 | LLK |
8.3 ± 0.1 | EI | Gilbert, Leach, et al., 1973 | LLK |
8.20 | EI | Cooks, Bertrand, et al., 1973 | LLK |
8.18 | CTS | Pitt, Carey, et al., 1972 | LLK |
8.8 ± 0.1 | EI | Gross, 1972 | LLK |
8.4 ± 0.1 | EI | Brown, 1970 | RDSH |
8.21 | PE | Dewar and Worley, 1969 | RDSH |
8.6 | EI | Williams, Cooks, et al., 1968 | RDSH |
8.22 ± 0.02 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
8.20 ± 0.02 | PI | Watanabe, 1957 | RDSH |
8.39 | PE | Klasinc, Kovac, et al., 1983 | Vertical value; LBLHLM |
8.45 | PE | Friege and Klessinger, 1979 | Vertical value; LLK |
8.42 | PE | Kobayashi, 1978 | Vertical value; LLK |
8.25 | PE | Benoit and Harrison, 1977 | Vertical value; LLK |
8.39 | PE | Kobayashi and Nagakura, 1974 | Vertical value; LLK |
8.46 | PE | Dewar, Ernstbrunner, et al., 1974 | Vertical value; LLK |
8.42 | PE | Bock and Wagner, 1972 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C5H5+ | 13.1 ± 0.1 | CH3+CO | PIPECO | Das, Gilman, et al., 1986 | LBLHLM |
C5H5+ | 13.5 | ? | EI | Harrison, Haynes, et al., 1965 | RDSH |
C6H5O+ | 11.70 ± 0.05 | CH3 | PI | Ponomarev, Arapov, et al., 1986 | LBLHLM |
C6H5O+ | 11.9 ± 0.1 | CH3 | PIPECO | Das, Gilman, et al., 1986 | LBLHLM |
C6H5O+ | 11.3 | CH3 | EI | McLafferty, Bente, et al., 1973 | LLK |
C6H5O+ | 11.8 ± 0.1 | CH3 | EI | Brown, 1970 | RDSH |
C6H5O+ | 11.9 ± 0.1 | CH3 | EI | Fisher, Palmer, et al., 1964 | RDSH |
C6H5O+ | 11.9 ± 0.1 | CH3 | EI | Tait, Shannon, et al., 1962 | RDSH |
C6H6+ | 10.85 ± 0.05 | CH2O | PI | Ziesel and Lifshitz, 1987 | LBLHLM |
C6H6+ | 11.4 ± 0.1 | CH2O | PIPECO | Das, Gilman, et al., 1986 | LBLHLM |
C6H6+ | 11.50 | HCHO | EI | Cooks, Bertrand, et al., 1973 | LLK |
C6H6+ | 11.6 ± 0.1 | HCHO | EI | Gross, 1972 | LLK |
C6H6+ | 11.3 ± 0.1 | CH2O | EI | Brown, 1970 | RDSH |
C6H6+ | 11.30 | ? | EI | Howe and Williams, 1969 | RDSH |
C6H7+ | 12.1 ± 0.1 | CHO | PIPECO | Das, Gilman, et al., 1986 | LBLHLM |
C6H7+ | 12.1 | CO+H? | EI | Harrison, Haynes, et al., 1965 | RDSH |
De-protonation reactions
C7H7O- + =
By formula: C7H7O- + H+ = C7H8O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 401.3 ± 3.1 | kcal/mol | G+TS | Dahlke and Kass, 1992 | gas phase; Acid: anisole. Between o-methoxyphenide and Me2NH.; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 394.0 ± 3.0 | kcal/mol | IMRB | Dahlke and Kass, 1992 | gas phase; Acid: anisole. Between o-methoxyphenide and Me2NH.; B |
C7H7O- + =
By formula: C7H7O- + H+ = C7H8O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 398.3 ± 3.1 | kcal/mol | G+TS | Dahlke and Kass, 1992 | gas phase; Acid: anisole. Between HO- and m,p-methoxyphenide; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 391.0 ± 3.0 | kcal/mol | IMRB | Dahlke and Kass, 1992 | gas phase; Acid: anisole. Between HO- and m,p-methoxyphenide; B |
C7H7O- + =
By formula: C7H7O- + H+ = C7H8O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 401.7 ± 3.1 | kcal/mol | G+TS | Dahlke and Kass, 1992 | gas phase; Acid: anisole. Between o-OMe-phenide and Me2NH.; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 394.0 ± 3.0 | kcal/mol | IMRB | Dahlke and Kass, 1992 | gas phase; Acid: anisole. Between o-OMe-phenide and Me2NH.; B |
References
Go To: Top, Gas phase ion energetics data, 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
. [all data]
Ponomarev, Arapov, et al., 1986
Ponomarev, D.A.; Arapov, O.V.; Sergeev, Y.L.; Chistyakov, A.B.,
[Title unavailable],
Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 1986, 29, 107. [all data]
Klasinc, Kovac, et al., 1983
Klasinc, L.; Kovac, B.; Gusten, H.,
Photoelectron spectra of acenes. Electronic structure and substituent effects,
Pure Appl. Chem., 1983, 55, 289. [all data]
Behan, Johnstone, et al., 1976
Behan, J.M.; Johnstone, R.A.W.; Bentley, T.W.,
An evaluation of empirical methods for calculating the ionization potentials of substituted benzenes,
Org. Mass Spectrom., 1976, 11, 207. [all data]
McLafferty, Bente, et al., 1973
McLafferty, F.W.; Bente, P.F., III; Kornfeld, R.; Tsai, S.-C.; Howe, I.,
Collisional activation spectra of organic ions,
J. Am. Chem. Soc., 1973, 95, 2120. [all data]
Maier and Turner, 1973
Maier, J.P.; Turner, D.W.,
Steric inhibition of resonance studied by molecular photoelectron spectroscopy Part 3. Anilines, Phenols and Related Compounds,
J. Chem. Soc. Faraday Trans. 2, 1973, 69, 521. [all data]
Kobayashi, Kobayashi, et al., 1973
Kobayashi, H.; Kobayashi, M.; Kaizu, Y.,
Molecular complexes of arenetricarbonylchromium,
Bull. Chem. Soc. Jpn., 1973, 46, 3109. [all data]
Gilbert, Leach, et al., 1973
Gilbert, J.R.; Leach, W.P.; Miller, J.R.,
Ionisation appearance potential measurements in arene chromium tricarbonyls,
J. Organomet. Chem., 1973, 49, 219. [all data]
Cooks, Bertrand, et al., 1973
Cooks, R.G.; Bertrand, M.; Beynon, J.H.; Rennekamp, M.E.; Setser, D.W.,
Energy partitioning data as an ion structure probe. Substituted anisoles,
J. Am. Chem. Soc., 1973, 95, 1732. [all data]
Pitt, Carey, et al., 1972
Pitt, C.G.; Carey, R.N.; Toren, E.C.,
Nature of the electronic interactions in aryl-substituted polysilanes,
J. Am. Chem. Soc., 1972, 94, 3806. [all data]
Gross, 1972
Gross, M.L.,
Ion cyclotron resonance spectrometry. A means of evaluating 'kinetic shifts',
Org. Mass Spectrom., 1972, 6, 827. [all data]
Brown, 1970
Brown, P.,
Kinetic studies in mass spectrometry. VIII. Competing [M-CH3] and [M-CH2O] reactions in substituted anisoles. Approximate activation energies from ionization appearance potentials,
Org. Mass Spectrom., 1970, 4, 519. [all data]
Dewar and Worley, 1969
Dewar, M.J.S.; Worley, S.D.,
Photoelectron spectra of molecules. I. Ionization potentials of some organic molecules and their interpretation,
J. Chem. Phys., 1969, 50, 654. [all data]
Williams, Cooks, et al., 1968
Williams, D.H.; Cooks, R.G.; Howe, I.,
Studies in mass spectrometry. XXXI. A comparison of reaction rates in common ions generated via fragmentation and direct ionization,
J. Am. Chem. Soc., 1968, 90, 6759. [all data]
Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J.,
Ionization potentials of some molecules,
J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]
Watanabe, 1957
Watanabe, K.,
Ionization potentials of some molecules,
J. Chem. Phys., 1957, 26, 542. [all data]
Friege and Klessinger, 1979
Friege, H.; Klessinger, M.,
Elektronenstruktur von Alkyl-aryl- und Alkyl-vinyl-ethern,
Chem. Ber., 1979, 112, 1614. [all data]
Kobayashi, 1978
Kobayashi, T.,
A simple general tendency in photoelectron angular distributions of some monosubstituted benzenes,
Phys. Lett., 1978, 69, 105. [all data]
Benoit and Harrison, 1977
Benoit, F.M.; Harrison, A.G.,
Predictive value of proton affinity. Ionization energy correlations involving oxygenated molecules,
J. Am. Chem. Soc., 1977, 99, 3980. [all data]
Kobayashi and Nagakura, 1974
Kobayashi, T.; Nagakura, S.,
Photoelectron spectra of substituted benzenes,
Bull. Chem. Soc. Jpn., 1974, 47, 2563. [all data]
Dewar, Ernstbrunner, et al., 1974
Dewar, P.S.; Ernstbrunner, E.; Gilmore, J.R.; Godfrey, M.; Mellor, J.M.,
Conformational analysis of alkyl aryl ethers and alkyl aryl sulphides by photoelectron spectroscopy,
Tetrahedron, 1974, 30, 2455. [all data]
Bock and Wagner, 1972
Bock, H.; Wagner, G.,
Electron lone pairs in organic sulfides and disulfides,
Angew. Chem. Int. Ed. Engl., 1972, 11, 119. [all data]
Das, Gilman, et al., 1986
Das, P.R.; Gilman, J.P.; Meisels, G.G.,
Unimolecular decomposition of energy-selected anisole ions. Breakdown graph and metastable decay rates,
Int. J. Mass Spectrom. Ion Processes, 1986, 68, 155. [all data]
Harrison, Haynes, et al., 1965
Harrison, A.G.; Haynes, P.; McLean, S.; Meyer, F.,
The mass spectra of methyl-substituted cyclopentadienes,
J. Am. Chem. Soc., 1965, 87, 5099. [all data]
Fisher, Palmer, et al., 1964
Fisher, I.P.; Palmer, T.F.; Lossing, F.P.,
The vertical ionization potentials of phenyl and phenoxy radicals,
J. Am. Chem. Soc., 1964, 86, 2741. [all data]
Tait, Shannon, et al., 1962
Tait, J.M.S.; Shannon, T.W.; Harrison, A.G.,
The structure of substituted C7 ions from benzyl derivatives at the appearance potential threshold,
J. Am. Chem. Soc., 1962, 84, 4. [all data]
Ziesel and Lifshitz, 1987
Ziesel, J.P.; Lifshitz, C.,
Time-dependent mass spectra and breakdown graphs. 10. Dissociative photoionization of anisole,
Chem. Phys., 1987, 117, 227. [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]
Dahlke and Kass, 1992
Dahlke, G.D.; Kass, S.R.,
The Ortho-dehydrophenoxy Anion,
Int. J. Mass Spectrom. Ion Proc., 1992, 117, 633, https://doi.org/10.1016/0168-1176(92)80117-J
. [all data]
Notes
Go To: Top, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy 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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