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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 C6H7N+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)7.720 ± 0.002eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)882.5kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity850.6kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
7.736 ± 0.008PEMeek, Sekreta, et al., 1985LBLHLM
7.720 ± 0.0002PIHager, Smith, et al., 1985LBLHLM
7.720 ± 0.002SSmith, Hager, et al., 1984LBLHLM
~7.48PEKlasinc, Kovac, et al., 1983LBLHLM
8.0PEKimura, Katsumata, et al., 1981LLK
8.27 ± 0.05EIZaretskii, Oren, et al., 1976LLK
7.80PEBehan, Johnstone, et al., 1976LLK
8.35EIBaldwin, Loudon, et al., 1976LLK
7.71 ± 0.01PEDebies and Rabalais, 1974LLK
7.65 ± 0.02PEMaier and Turner, 1973LLK
7.6 ± 0.1EIGilbert, Leach, et al., 1973LLK
7.71PEDebies and Rabalais, 1973LLK
7.66PECowling and Johnstone, 1973LLK
7.63EICooks, Bertrand, et al., 1973LLK
7.89 ± 0.03EIJohnstone and Mellon, 1972LLK
8.1 ± 0.1EIGross, 1972LLK
7.70 ± 0.01PIPotapov and Iskakov, 1971LLK
7.89EIJohnstone, Mellon, et al., 1971LLK
7.61 ± 0.05SIZandberg and Rasulev, 1969RDSH
7.68PEEland, 1969RDSH
7.67 ± 0.03PIAkopyan and Vilesov, 1964RDSH
7.7PITerenin, 1961RDSH
7.70 ± 0.02PIWatanabe and Mottl, 1957RDSH
7.69 ± 0.02PIVilesov and Terenin, 1957RDSH
8.05PEFurin, Sultanov, et al., 1987Vertical value; LBLHLM
8.02PEKlasinc, Kovac, et al., 1983Vertical value; LBLHLM
8.04PEMeeks, Wahlborg, et al., 1981Vertical value; LLK
8.05PEPalmer, Moyes, et al., 1979Vertical value; LLK
8.03PEKobayashi, 1978Vertical value; LLK
8.05PEKobayashi and Nagakura, 1974Vertical value; LLK
8.10PEHaink, Adams, et al., 1974Vertical value; LLK
8.02PEDebies and Rabalais, 1973Vertical value; LLK
8.05PEKobayashi and Nagakura, 1972Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C4H4N+12.3 ± 0.1?PIAkopyan and Vilesov, 1964RDSH
C5H5+15.2 ± 0.2CHN+HEITajima and Tsuchiya, 1973LLK
C5H5+15.24CHN+HEIOccolowitz and White, 1968RDSH
C5H6+11.3 ± 0.1CHNTRPILifshitz and Malinovich, 1984LBLHLM
C5H6+11.3 ± 0.2CHNEILifshitz, Gotchiguian, et al., 1983LBLHLM
C5H6+12.77 ± 0.05CHNEIZaretskii, Oren, et al., 1976LLK
C5H6+12.13 ± 0.06CHNEIBentley, Johnstone, et al., 1973LLK
C5H6+12.0 ± 0.1?EIGross, 1972LLK
C5H6+12.3 ± 0.1CHNPIAkopyan and Vilesov, 1964RDSH

De-protonation reactions

C6H6N- + Hydrogen cation = Aniline

By formula: C6H6N- + H+ = C6H7N

Quantity Value Units Method Reference Comment
Δr1540.5 ± 1.3kJ/molD-EAWren, Vogelhuber, et al., 2012gas phase; B
Δr1533. ± 8.8kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr1510.0 ± 2.8kJ/molH-TSWren, Vogelhuber, et al., 2012gas phase; B
Δr1502. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B


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, . [all data]

Meek, Sekreta, et al., 1985
Meek, J.T.; Sekreta, E.; Wilson, W.; Viswanathan, K.S.; Reilly, J.P., The laser photoelectron spectrum of gas phase aniline, J. Chem. Phys., 1985, 82, 1741. [all data]

Hager, Smith, et al., 1985
Hager, J.; Smith, M.; Wallace, S., Autoionizing Rydberg structure observed in the vibrationally selective, two-color threshold photoionization spectrum of jet-cooled aniline, J. Chem. Phys., 1985, 83, 4820. [all data]

Smith, Hager, et al., 1984
Smith, M.A.; Hager, J.W.; Wallace, S.C., Two color photoionization spectroscopy of jet cooled aniline: Vibrational frequencies of the aniline X2B1 radical cation, J. Chem. Phys., 1984, 80, 3097. [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]

Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S., Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]

Zaretskii, Oren, et al., 1976
Zaretskii, Z.V.I.; Oren, D.; Kelner, L., Automatic method for the measurement of the electron impact ionization and appearance potentials, Appl. Spectrosc., 1976, 30, 366. [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]

Baldwin, Loudon, et al., 1976
Baldwin, M.A.; Loudon, A.G.; Maccoll, A.; Webb, K.S., The nature and fragmentation pathways of the molecular ions of some arylureas, arylthioureas, acetanilides, thioacetanilides and related compounds, Org. Mass Spectrom., 1976, 11, 1181. [all data]

Debies and Rabalais, 1974
Debies, T.P.; Rabalais, J.W., Photoelectron spectra of substituted benzenes. III. Bonding with Group V substituents, Inorg. Chem., 1974, 13, 308. [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]

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]

Debies and Rabalais, 1973
Debies, T.P.; Rabalais, J.W., Photoelectron spectra of substituted benzenes. II. Seven valence electron substituents, J. Electron Spectrosc. Relat. Phenom., 1973, 1, 355. [all data]

Cowling and Johnstone, 1973
Cowling, S.A.; Johnstone, R.A.W., Photoelectron spectroscopy: The effects of steric inhibition to resonance in anilines, J. Electron Spectrosc. Relat. Phenom., 1973, 2, 161. [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]

Johnstone and Mellon, 1972
Johnstone, R.A.W.; Mellon, F.A., Electron-impact ionization and appearance potentials, J. Chem. Soc. Faraday Trans. 2, 1972, 68, 1209. [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]

Potapov and Iskakov, 1971
Potapov, V.K.; Iskakov, L.I., Electronic structure and photoionization of aromatic amines, High Energy Chem., 1971, 5, 237, In original 264. [all data]

Johnstone, Mellon, et al., 1971
Johnstone, R.A.W.; Mellon, F.A.; Ward, S.D., On-line computer methods used in conjunction with the measurement of ionization appearance potentials, Adv. Mass Spectrom., 1971, 5, 334. [all data]

Zandberg and Rasulev, 1969
Zandberg, E.Ya.; Rasulev, U.Kh., Surface ionization of aniline molecules, Zh. Tekhn. Fiz. 1968,38,1798 (Engl. Transl.: Soviet Phys. - Tech. Phys., 1969, 13, 1450). [all data]

Eland, 1969
Eland, J.H.D., Photoelectron spectra of conjugated hydrocarbons and heteromolecules, Intern. J. Mass Spectrom. Ion Phys., 1969, 2, 471. [all data]

Akopyan and Vilesov, 1964
Akopyan, M.E.; Vilesov, F.I., Excited states of positive ions and dissociative photoionization of aromatic amines, Dokl. Akad. Nauk SSSR, 1964, 158, 1386, In original 965. [all data]

Terenin, 1961
Terenin, A., Charge transfer in organic solids, induced by light, Proc. Chem. Soc., London, 1961, 321. [all data]

Watanabe and Mottl, 1957
Watanabe, K.; Mottl, J.R., Ionization potentials of ammonia and some amines, J. Chem. Phys., 1957, 26, 1773. [all data]

Vilesov and Terenin, 1957
Vilesov, F.I.; Terenin, A.N., The photoionization of the vapors of certain organic compounds, Dokl. Akad. Nauk SSSR, 1957, 115, 744, In original 539. [all data]

Furin, Sultanov, et al., 1987
Furin, G.G.; Sultanov, A.S.; Furlei, I.I., Photoelectronic spectra of fluorine-containing aromatic amines, Dokl. Phys. Chem., 1987, 530. [all data]

Meeks, Wahlborg, et al., 1981
Meeks, J.; Wahlborg, A.; McGlynn, S.P., Photoelectron spectroscopy of carbonyls: Benzoic acid and its derivatives, J. Electron Spectrosc. Relat. Phenom., 1981, 22, 43. [all data]

Palmer, Moyes, et al., 1979
Palmer, M.H.; Moyes, W.; Spiers, M.; Ridyard, J.N.A., The electronic structure of substituted benzenes; a study of aniline, the toluidines, phenylenediamines and fluoroanilines by photoelectron spectroscopy and ab initio calculations, J. Mol. Struct., 1979, 53, 235. [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]

Kobayashi and Nagakura, 1974
Kobayashi, T.; Nagakura, S., Photoelectron spectra of substituted benzenes, Bull. Chem. Soc. Jpn., 1974, 47, 2563. [all data]

Haink, Adams, et al., 1974
Haink, H.J.; Adams, J.E.; Huber, J.R., The electronic structure of aromatic amines: photoelectron spectroscopy of diphenylamine, iminobibenzyl, acridan and carbazole, Ber. Bunsen-Ges. Phys. Chem., 1974, 78, 436. [all data]

Kobayashi and Nagakura, 1972
Kobayashi, T.; Nagakura, S., Photoelectron spectra of anilines, Chem. Lett., 1972, 1013. [all data]

Tajima and Tsuchiya, 1973
Tajima, S.; Tsuchiya, T., Energetics consideration of C5H5+ ions produced from various precursors by electron impact, Bull. Chem. Soc. Jpn., 1973, 46, 3291. [all data]

Occolowitz and White, 1968
Occolowitz, J.L.; White, G.L., Energetic considerations in the assignment of some fragment ion structures, Australian J. Chem., 1968, 21, 997. [all data]

Lifshitz and Malinovich, 1984
Lifshitz, C.; Malinovich, Y., Time resolved photoionization mass spectrometry in the millisecond range, Int. J. Mass Spectrom. Ion Processes, 1984, 60, 99. [all data]

Lifshitz, Gotchiguian, et al., 1983
Lifshitz, C.; Gotchiguian, P.; Roller, R., Time-dependent mass spectra and breakdown graphs. The kinetic shift in aniline, Chem. Phys. Lett., 1983, 95, 106. [all data]

Bentley, Johnstone, et al., 1973
Bentley, T.W.; Johnstone, R.A.W.; McMaster, B.N., Appearance potentials of metastable and normal ions and the kinetic shift, J. Chem. Soc., Chem. Commun., 1973, 510. [all data]

Wren, Vogelhuber, et al., 2012
Wren, S.W.; Vogelhuber, K.M.; Ichino, T.; Stanton, J.F.; Lineberger, W.C., Photoelectron Spectroscopy of Anilinide and Acidity of Aniline, J. Phys. Chem. A, 2012, 116, 12, 3118-3123, . [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]


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