Benzene, 1-methyl-2-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
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

View reactions leading to C7H7NO2+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)9.24eVN/AN/AL

Electron affinity determinations

EA (eV) Method Reference Comment
0.92 ± 0.10TDEqChowdhury, Heinis, et al., 1986ΔGea(423 K) = -20.7 kcal/mol; ΔSea = -1.6 eu.; B
0.954 ± 0.048IMREFukuda and McIver, 1985ΔGea(355 K) = -21.4 kcal/mol; ΔSea =-1.6, est. from data in Chowdhury, Heinis, et al., 1986; B
0.880 ± 0.030ECDChen, Chen, et al., 1992B
<1.240 ± 0.050PDMock and Grimsrud, 1989B

Ionization energy determinations

IE (eV) Method Reference Comment
9.24PIPECOShao and Baer, 1988LL
9.51 ± 0.03EIBaldwin, Carter, et al., 1982LBLHLM
9.50PEPalmer, Moyes, et al., 1979LLK
9.43 ± 0.05PIMatyuk, Potapov, et al., 1979LLK
9.63PEKobayashi and Nagakura, 1974Vertical value; LLK
10.2 ± 0.1SIGol'denfel'd, Korostyshevskii, et al., 1973Vertical value; LLK
9.69 ± 0.015PEKobayashi and Nagakura, 1972Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C5H5+14.8C2H2+NO2EITajima and Tsuchiya, 1973LLK
C5H5+13.5 ± 0.2HCN+CO+OHEITajima and Tsuchiya, 1973LLK
C7H6NO+≤9.69OHPIPECOShao and Baer, 1988LL
C7H6NO+9.69 ± 0.05OHPIMatyuk, Potapov, et al., 1979LLK
C7H7+11.0 ± 0.1NO2PIMatyuk, Potapov, et al., 1979LLK
C7H7+13.1 ± 0.3NO2EIMcLafferty and Winkler, 1974LLK

De-protonation reactions

C7H6NO2- + Hydrogen cation = Benzene, 1-methyl-2-nitro-

By formula: C7H6NO2- + H+ = C7H7NO2

Quantity Value Units Method Reference Comment
Δr1490. ± 8.8kJ/molG+TSTaft, 1987gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr1459. ± 8.4kJ/molIMRETaft, 1987gas phase; value altered from reference due to change in acidity scale; B

Mass spectrum (electron ionization)

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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

Spectrum

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Additional Data

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin NIST Mass Spectrometry Data Center, 1992
NIST MS number 125379

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Gas Chromatography

Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), References, Notes

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
PackedSE-30150.1155.Tiess, 1984Ar, Gas Chrom Q (80-100 mesh); Column length: 3. m
PackedApiezon L130.1155.Wehrli and Kováts, 1959Celite; Column length: 2.25 m

Kovats' RI, polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
PackedCarbowax 20M200.1877.Vernon and Suratman, 1983He, Silanized white support; Column length: 2. m

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

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Column type Active phase I Reference Comment
CapillaryDB-5MS194.65Chen, 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, Mass spectrum (electron ionization), 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]

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]

Shao and Baer, 1988
Shao, J.D.; Baer, T., The dissociation dynamics of energy selected o-nitrotoluene ions, Int. J. Mass Spectrom. Ion Processes, 1988, 86, 357. [all data]

Baldwin, Carter, et al., 1982
Baldwin, M.A.; Carter, D.M.; Gilmore, J., Loss of hydroxyl radical from isomeric ethylnitrobenzenes, Org. Mass Spectrom., 1982, 17, 45. [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]

Matyuk, Potapov, et al., 1979
Matyuk, V.M.; Potapov, V.K.; Prokhoda, A.L., Photoexcitation and photoionisation of nitro- derivatives of benzene and toluene, Russ. J. Phys. Chem., 1979, 53, 538. [all data]

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

Gol'denfel'd, Korostyshevskii, et al., 1973
Gol'denfel'd, I.V.; Korostyshevskii, I.Z.; Mischanchuk, B.G.; Pokrovskii, V.A., Determination of ionization potentials of atoms and molecules using a field mass spectrometer equipped with an energy analyzer, Dokl. Akad. Nauk SSSR, 1973, 213, 626. [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]

Taft, 1987
Taft, R.W., The Nature and Analysis of Substitutent Electronic Effects, Personal communication. See also Prog. Phys. Org. Chem., 1987, 16, 1. [all data]

Tiess, 1984
Tiess, D., Gaschromatographische Retentionsindices von 125 leicht- bis mittelflüchtigen organischen Substanzen toxikologisch-analytischer Relevanz auf SE-30, Wiss. Z. Wilhelm-Pieck-Univ. Rostock Math. Naturwiss. Reihe, 1984, 33, 6-9. [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]

Vernon and Suratman, 1983
Vernon, F.; Suratman, J.B., The retention index system applied to alkylbenzenes and monosubstituted derivatives, Chromatographia, 1983, 17, 11, 600-604, https://doi.org/10.1007/BF02261943 . [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

Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References