Benzene, 1-methyl-3-nitro-

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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:
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
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 C7H7NO2+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)9.5 ± 0.1eVN/AN/AL

Electron affinity determinations

EA (eV) Method Reference Comment
0.99 ± 0.10IMREChowdhury, Heinis, et al., 1986ΔGea(423 K) = -22.1 kcal/mol; ΔSea (estimated) = -1.7 eu.; B
0.984 ± 0.048IMREFukuda and McIver, 1985ΔGea(355 K) = -22.1 kcal/mol; ΔSea =-1.7, est. from data in Chowdhury, Heinis, et al., 1986; B
0.970 ± 0.030ECDChen, Chen, et al., 1992B
0.927993IMRBHan and Brauman, 1988B
<1.180 ± 0.050PDMock and Grimsrud, 1989B
0.80 ± 0.10ECDZlatkis, Lee, et al., 1983B

Ionization energy determinations

IE (eV) Method Reference Comment
9.5 ± 0.1PIPECOBaer, Morrow, et al., 1988LL
9.50PEPalmer, Moyes, et al., 1979LLK
9.5 ± 0.1EIBrown, 1970RDSH
9.65 ± 0.05EIPignataro, Foffani, et al., 1966RDSH
9.48PEKobayashi and Nagakura, 1974Vertical value; LLK
9.49 ± 0.015PEKobayashi and Nagakura, 1972Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C5H5+15.2 ± 0.2C2H2+NO2EITajima and Tsuchiya, 1973LLK
C7H7+11.01NO2PIPECOBaer, Morrow, et al., 1988T = 0K; LL
C7H7+11.08NO2PIPECOBaer, Morrow, et al., 1988T = 298K; LL
C7H7+12.1 ± 0.3NO2EIMcLafferty and Winkler, 1974LLK
C7H7+11.6 ± 0.1NO2EIBrown, 1970RDSH
C7H7O+10. ± 0.1NOEIBrown, 1970RDSH

De-protonation reactions

C7H6NO2- + Hydrogen cation = Benzene, 1-methyl-3-nitro-

By formula: C7H6NO2- + H+ = C7H7NO2

Quantity Value Units Method Reference Comment
Δr1518. ± 8.8kJ/molG+TSCaldwell and Bartmessgas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr1488. ± 8.4kJ/molIMRECaldwell and Bartmessgas phase; value altered from reference due to change in acidity scale; B

Gas Chromatography

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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 compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
PackedApiezon L130.1201.Wehrli and Kováts, 1959Celite; Column length: 2.25 m

Lee's RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-5MS202.07Chen, Keeran, et al., 200230. m/0.25 mm/0.5 μm, 40. C @ 1. min, 10. K/min; Tend: 310. C

References

Go To: Top, Gas phase ion energetics data, Gas Chromatography, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Chowdhury, Heinis, et al., 1986
Chowdhury, S.; Heinis, T.; Grimsrud, E.P.; Kebarle, P., Entropy Changes and Electron Affinities from Gas-Phase Electron Transfer Equilibria: A- + B = A + B-, J. Phys. Chem., 1986, 90, 12, 2747, https://doi.org/10.1021/j100403a037 . [all data]

Fukuda and McIver, 1985
Fukuda, E.K.; McIver, R.T., Jr., Relative electron affinities of substituted benzophenones, nitrobenzenes, and quinones. [Anchored to EA(SO2) from 74CEL/BEN], J. Am. Chem. Soc., 1985, 107, 2291. [all data]

Chen, Chen, et al., 1992
Chen, E.C.M.; Chen, E.S.; Milligan, M.S.; Wentworth, W.E.; Wiley, J.R., Experimental Determination of the Electron Affinities of Nitrobenzene, Nitrotoluenes, Pentafluoronitrobenzene, and Isotopic Nitrobenzenes an, J. Phys. Chem., 1992, 96, 5, 2385, https://doi.org/10.1021/j100184a069 . [all data]

Han and Brauman, 1988
Han, C.-C.; Brauman, J.I., Electron Transfer Competes with Proton Transfer in Gas-phase Acid-base Reactions, J. Am. Chem. Soc., 1988, 110, 12, 4048, https://doi.org/10.1021/ja00220a059 . [all data]

Mock and Grimsrud, 1989
Mock, R.S.; Grimsrud, E.P., Gas-Phase Electron Photodetachment Spectroscopy of the Molecular Anions of Nitroaromatic Hydrocarbons at Atmospheric Pressure, J. Am. Chem. Soc., 1989, 111, 8, 2861, https://doi.org/10.1021/ja00190a020 . [all data]

Zlatkis, Lee, et al., 1983
Zlatkis, A.; Lee, C.K.; Wentworth, W.E.; Chen, E.C.M., Constant current linearization for determination of electron capture mechanisms, Anal. Chem., 1983, 55, 1596. [all data]

Baer, Morrow, et al., 1988
Baer, T.; Morrow, J.C.; Shao, J.D.; Olesik, S., Gas-phase heats of formation of C7H7+ isomers: m-Tolyl, p-tolyl, and benzyl ions, J. Am. Chem. Soc., 1988, 110, 5633. [all data]

Palmer, Moyes, et al., 1979
Palmer, M.H.; Moyes, W.; Spiers, M.; Ridyard, J.N.A., The electronic structure of substituted benzenes; ab initio calculations and photoelectron spectra for nitrobenzene, the nitrotoluenes, dinitrobenzenes and fluoronitrobenzenes, J. Mol. Struct., 1979, 55, 243. [all data]

Brown, 1970
Brown, P., Kinetic studies in mass spectrometry. IX. Competing [M-NO2] and [M-NO] reactions in substituted nitrobenzenes. Approximate activation energies from ionization and appearance potentials, Org. Mass Spectrom., 1970, 4, 533. [all data]

Pignataro, Foffani, et al., 1966
Pignataro, S.; Foffani, A.; Innorta, G.; Distefano, G., Molecular structural effects on the ionization potentials for metasubstituted aromatic compounds and for compounds of the type X-CH2-R, Z. Physik. Chem. (Frankfurt), 1966, 49, 291. [all data]

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

Kobayashi and Nagakura, 1972
Kobayashi, T.; Nagakura, S., Photoelectron spectra of nitro-compounds, Chem. Lett., 1972, 903. [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]

McLafferty and Winkler, 1974
McLafferty, F.W.; Winkler, J., Gaseous tropylium, benzyl, tolyl, and norbornadienyl cations, J. Am. Chem. Soc., 1974, 96, 5182. [all data]

Caldwell and Bartmess
Caldwell, G.; Bartmess, J.E., , Unpublished results. [all data]

Wehrli and Kováts, 1959
Wehrli, A.; Kováts, E., Gas-chromatographische Charakterisierung ogranischer Verbindungen. Teil 3: Berechnung der Retentionsindices aliphatischer, alicyclischer und aromatischer Verbindungen, Helv. Chim. Acta, 1959, 7, 7, 2709-2736, https://doi.org/10.1002/hlca.19590420745 . [all data]

Chen, Keeran, et al., 2002
Chen, P.H.; Keeran, W.S.; Van Ausdale, W.A.; Schindler, D.R.; Roberts, D.W., Application of Lee retention indices to the confirmation of tentatively identified compounds from GC/MS analysis of environmental samples, Technical paper, Analytical Services Division, Environmental ScienceEngineering, Inc, PO Box 1703, Gainesville, FL 32602, 2002, 11. [all data]


Notes

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