Anisole

• Formula: C₇H₈O
• Molecular weight: 108.1378
• IUPAC Standard InChI: InChI=1S/C7H8O/c1-8-7-5-3-2-4-6-7/h2-6H,1H3 Copy

  
• IUPAC Standard InChIKey: RDOXTESZEPMUJZ-UHFFFAOYSA-N Copy
• 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
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Henry's Law data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
  • X-ray Photoelectron Spectroscopy Database, version 5.0
  • X-ray Photoelectron Spectroscopy Database, version 5.0
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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)

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₇H₇O^- +  =

By formula: C₇H₇O^- + H⁺ = C₇H₈O

C₇H₇O^- +  =

By formula: C₇H₇O^- + H⁺ = C₇H₈O

C₇H₇O^- +  =

By formula: C₇H₇O^- + H⁺ = C₇H₈O

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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