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Anisole

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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
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 ± 0.05eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)200.7kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity192.9kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.25 ± 0.03PIPonomarev, Arapov, et al., 1986LBLHLM
~8.10PEKlasinc, Kovac, et al., 1983LBLHLM
8.24PEBehan, Johnstone, et al., 1976LLK
8.6EIMcLafferty, Bente, et al., 1973LLK
8.20 ± 0.02PEMaier and Turner, 1973LLK
8.37CTSKobayashi, Kobayashi, et al., 1973LLK
8.3 ± 0.1EIGilbert, Leach, et al., 1973LLK
8.20EICooks, Bertrand, et al., 1973LLK
8.18CTSPitt, Carey, et al., 1972LLK
8.8 ± 0.1EIGross, 1972LLK
8.4 ± 0.1EIBrown, 1970RDSH
8.21PEDewar and Worley, 1969RDSH
8.6EIWilliams, Cooks, et al., 1968RDSH
8.22 ± 0.02PIWatanabe, Nakayama, et al., 1962RDSH
8.20 ± 0.02PIWatanabe, 1957RDSH
8.39PEKlasinc, Kovac, et al., 1983Vertical value; LBLHLM
8.45PEFriege and Klessinger, 1979Vertical value; LLK
8.42PEKobayashi, 1978Vertical value; LLK
8.25PEBenoit and Harrison, 1977Vertical value; LLK
8.39PEKobayashi and Nagakura, 1974Vertical value; LLK
8.46PEDewar, Ernstbrunner, et al., 1974Vertical value; LLK
8.42PEBock and Wagner, 1972Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C5H5+13.1 ± 0.1CH3+COPIPECODas, Gilman, et al., 1986LBLHLM
C5H5+13.5?EIHarrison, Haynes, et al., 1965RDSH
C6H5O+11.70 ± 0.05CH3PIPonomarev, Arapov, et al., 1986LBLHLM
C6H5O+11.9 ± 0.1CH3PIPECODas, Gilman, et al., 1986LBLHLM
C6H5O+11.3CH3EIMcLafferty, Bente, et al., 1973LLK
C6H5O+11.8 ± 0.1CH3EIBrown, 1970RDSH
C6H5O+11.9 ± 0.1CH3EIFisher, Palmer, et al., 1964RDSH
C6H5O+11.9 ± 0.1CH3EITait, Shannon, et al., 1962RDSH
C6H6+10.85 ± 0.05CH2OPIZiesel and Lifshitz, 1987LBLHLM
C6H6+11.4 ± 0.1CH2OPIPECODas, Gilman, et al., 1986LBLHLM
C6H6+11.50HCHOEICooks, Bertrand, et al., 1973LLK
C6H6+11.6 ± 0.1HCHOEIGross, 1972LLK
C6H6+11.3 ± 0.1CH2OEIBrown, 1970RDSH
C6H6+11.30?EIHowe and Williams, 1969RDSH
C6H7+12.1 ± 0.1CHOPIPECODas, Gilman, et al., 1986LBLHLM
C6H7+12.1CO+H?EIHarrison, Haynes, et al., 1965RDSH

De-protonation reactions

C7H7O- + Hydrogen cation = Anisole

By formula: C7H7O- + H+ = C7H8O

Quantity Value Units Method Reference Comment
Deltar401.3 ± 3.1kcal/molG+TSDahlke and Kass, 1992gas phase; Acid: anisole. Between o-methoxyphenide and Me2NH.; B
Quantity Value Units Method Reference Comment
Deltar394.0 ± 3.0kcal/molIMRBDahlke and Kass, 1992gas phase; Acid: anisole. Between o-methoxyphenide and Me2NH.; B

C7H7O- + Hydrogen cation = Anisole

By formula: C7H7O- + H+ = C7H8O

Quantity Value Units Method Reference Comment
Deltar398.3 ± 3.1kcal/molG+TSDahlke and Kass, 1992gas phase; Acid: anisole. Between HO- and m,p-methoxyphenide; B
Quantity Value Units Method Reference Comment
Deltar391.0 ± 3.0kcal/molIMRBDahlke and Kass, 1992gas phase; Acid: anisole. Between HO- and m,p-methoxyphenide; B

C7H7O- + Hydrogen cation = Anisole

By formula: C7H7O- + H+ = C7H8O

Quantity Value Units Method Reference Comment
Deltar401.7 ± 3.1kcal/molG+TSDahlke and Kass, 1992gas phase; Acid: anisole. Between o-OMe-phenide and Me2NH.; B
Quantity Value Units Method Reference Comment
Deltar394.0 ± 3.0kcal/molIMRBDahlke and Kass, 1992gas 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