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Naphthalene, 1-methyl-

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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
MM - Michael M. Meot-Ner (Mautner)
LL - Sharon G. Lias and Joel F. Liebman
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 C11H10+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)7.96 ± 0.03eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)834.8kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity805.3kJ/molN/AHunter and Lias, 1998HL

Electron affinity determinations

EA (eV) Method Reference Comment
<0.16 ± 0.12ECDWojnarovits and Foldiak, 1981EA is an upper limit: Chen and Wentworth, 1989. G3MP2B3 calculations indicate an EA of ca. -0.1 eV, anion unbound.; B

Proton affinity at 298K

Proton affinity (kJ/mol) Reference Comment
831.4Aue, Guidoni, et al., 2000Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM

Gas basicity at 298K

Gas basicity (review) (kJ/mol) Reference Comment
803.3Aue, Guidoni, et al., 2000Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM

Ionization energy determinations

IE (eV) Method Reference Comment
7.90 ± 0.02PIGotkis and Lifshitz, 1993LL
8.50 ± 0.05EILoudon and Mazengo, 1974LLK
7.98CTSPitt, Carey, et al., 1972LLK
7.80 ± 0.03EIBonnier, Gelus, et al., 1965RDSH
7.98CTSKinoshita, 1962RDSH
7.96 ± 0.01PIWatanabe, 1957RDSH
8.01 ± 0.03PEHeilbronner, Hoshi, et al., 1976Vertical value; LLK
7.95PEHeilbronner, Hornung, et al., 1972Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C11H9+12.1 ± 0.1HTRPIGotkis and Lifshitz, 1993LL
C11H9+10.2 ± 0.2HPIHuang and Dunbar, 1990LL
C11H9+13.2 ± 0.2HEILoudon and Mazengo, 1974LLK
C11H9+12.4 ± 0.1HEINounou, 1966RDSH

De-protonation reactions

C11H9- + Hydrogen cation = Naphthalene, 1-methyl-

By formula: C11H9- + H+ = C11H10

Quantity Value Units Method Reference Comment
Deltar1565. ± 8.8kJ/molG+TSBartmess and Griffiths, 1990gas phase; Isomer 1-methylene-1,4-dihydronaphthalene: «DELTA»G=349.0±2.0, «DELTA»S=27±2, «DELTA»H=357.1; B
Deltar1551. ± 10.kJ/molTDEqMeot-ner, Liebman, et al., 1988gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B
Quantity Value Units Method Reference Comment
Deltar1531. ± 8.4kJ/molIMREBartmess and Griffiths, 1990gas phase; Isomer 1-methylene-1,4-dihydronaphthalene: «DELTA»G=349.0±2.0, «DELTA»S=27±2, «DELTA»H=357.1; B
Deltar1516. ± 8.4kJ/molTDEqMeot-ner, Liebman, et al., 1988gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; 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]

Wojnarovits and Foldiak, 1981
Wojnarovits, L.; Foldiak, G., Electron capture detection of aromatic hydrocarbons, J. Chromatogr. Sci., 1981, 206, 511. [all data]

Chen and Wentworth, 1989
Chen, E.C.M.; Wentworth, W.E., Experimental Determination of Electron Affinities of Organic Molecules, Mol. Cryst. Liq. Cryst., 1989, 171, 271. [all data]

Aue, Guidoni, et al., 2000
Aue, D.H.; Guidoni, M.; Betowski, L.D., Ab initio calculated gas-phase basicities of polynuclear aromatic hydrocarbons, Int. J. Mass Spectrom., 2000, 201, 283. [all data]

Gotkis and Lifshitz, 1993
Gotkis, I.; Lifshitz, C., Time-dependent mass spectra and breakdown graphs. 16 - The methylnaphthalenes, Org. Mass Spectrom., 1993, 28, 372. [all data]

Loudon and Mazengo, 1974
Loudon, A.G.; Mazengo, R.Z., Steric strain and electron-impact. The behaviour of some n, n'-dimethyl- 1,1-binaphthyls, some n, n'-dimethylbiphenyls and model compounds, Org. Mass Spectrom., 1974, 8, 179. [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]

Bonnier, Gelus, et al., 1965
Bonnier, J.-M.; Gelus, M.; Nounou, P., Contribution a l'etude de l'effet inductif et de l'effet d'hyperconjugaison dans quelques methylaromatiques, J. Chim. Phys., 1965, 10, 1191. [all data]

Kinoshita, 1962
Kinoshita, M., The absorption spectra of the molecular complexes of aromatic compounds with p-bromanil, Bull. Chem. Soc. Japan, 1962, 35, 1609. [all data]

Watanabe, 1957
Watanabe, K., Ionization potentials of some molecules, J. Chem. Phys., 1957, 26, 542. [all data]

Heilbronner, Hoshi, et al., 1976
Heilbronner, E.; Hoshi, T.; von Rosenberg, J.L.; Hafner, K., Alkyl-induced, natural hypsochromic shifts of the 2A<--2X and 2B<--2X transitions of azulene and naphthalene radical cations, Nouv. J. Chim., 1976, 1, 105. [all data]

Heilbronner, Hornung, et al., 1972
Heilbronner, E.; Hornung, V.; Pinkerton, F.H.; Thames, S.F., 31. Photoelectron spectra of azabenzenes and azanaphthalenes: III. The orbital sequence in methyl- and trimethylsilyl- substituted pyridines, Helv. Chim. Acta, 1972, 55, 289. [all data]

Huang and Dunbar, 1990
Huang, F.-S.; Dunbar, R.C., Time-resolved photodissociation of methylnaphthalene ion. An illustration of kinetic shifts in large-ion dissociations, J. Am. Chem. Soc., 1990, 112, 8167. [all data]

Nounou, 1966
Nounou, P., Etude des composes aromatiques par spectrometrie de masse. I. Mesure des potentials d'ionisation et d'apparition par la methode du potential retardateur et interpretation des courbes d'ionisation differentielle, J. Chim. Phys., 1966, 63, 994. [all data]

Bartmess and Griffiths, 1990
Bartmess, J.E.; Griffiths, S.S., Tautomerization Energetics of Benzoannelated Toluenes, J. Am. Chem. Soc., 1990, 112, 8, 2932, https://doi.org/10.1021/ja00164a014 . [all data]

Meot-ner, Liebman, et al., 1988
Meot-ner, M.; Liebman, J.F.; Kafafi, S.A., Ionic Probes of Aromaticity in Annelated Rings, J. Am. Chem. Soc., 1988, 110, 18, 5937, https://doi.org/10.1021/ja00226a001 . [all data]

Kiefer, Zhang, et al., 1997
Kiefer, J.H.; Zhang, Q.; Kern, R.D.; Yao, J.; Jursic, B., Pyrolysis of Aromatic Azines: Pyrazine, Pyrimidine, and Pyridine, J. Phys. Chem. A, 1997, 101, 38, 7061, https://doi.org/10.1021/jp970211z . [all data]


Notes

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