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Benzene, 1-methyl-3-nitro-

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Condensed phase thermochemistry data

Go To: Top, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References, Notes

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

Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Deltafliquid-46.0kJ/molCcbSwarts, 1914See 14SWA2; ALS
Quantity Value Units Method Reference Comment
Deltacliquid-3723.5 ± 3.3kJ/molCcbLenchitz, Velicky, et al., 1971ALS
Deltacliquid-3737.kJ/molCcbGarner and Abernethy, 1921ALS
Deltacliquid-3721.9kJ/molCcbSwarts, 1914See 14SWA2; ALS

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
202.1302.4de Kolossowsky and Udowenko, 1934DH

Phase change data

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References, Notes

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

Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny, director
AC - William E. Acree, Jr., James S. Chickos

Quantity Value Units Method Reference Comment
Tboil503.7KN/AAldrich Chemical Company Inc., 1990BS
Tboil505.8KN/AWeast and Grasselli, 1989BS
Tboil503.95KN/ALecat, 1930Uncertainty assigned by TRC = 0.4 K; not clear that this is a new measurement; TRC
Tboil504.KN/ADessart, 1926Uncertainty assigned by TRC = 0.4 K; TRC
Quantity Value Units Method Reference Comment
Tfus288.59KN/AGross, Saylor, et al., 1933Uncertainty assigned by TRC = 0.2 K; TRC
Tfus289.KN/ADessart, 1926Uncertainty assigned by TRC = 2. K; TRC

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
56.6 ± 2.5303.GSWidegren and Bruno, 2010Based on data from 293. - 313. K.; AC
52.8413.EBAim, 1994Based on data from 397. - 452. K.; AC
49.8368.AStephenson and Malanowski, 1987Based on data from 353. - 505. K.; AC

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


Reaction thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References, Notes

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

Data compiled as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

Bromine anion + Benzene, 1-methyl-3-nitro- = (Bromine anion bullet Benzene, 1-methyl-3-nitro-)

By formula: Br- + C7H7NO2 = (Br- bullet C7H7NO2)

Quantity Value Units Method Reference Comment
Deltar66.5 ± 7.5kJ/molIMREPaul and Kebarle, 1991gas phase; «DELTA»Gaff at 423 K, «DELTA»Saff taken as that of mCF3-nitrobenzene..Br-; B,M
Quantity Value Units Method Reference Comment
Deltar92.J/mol*KN/APaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar27. ± 4.2kJ/molIMREPaul and Kebarle, 1991gas phase; «DELTA»Gaff at 423 K, «DELTA»Saff taken as that of mCF3-nitrobenzene..Br-; B

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
26.423.PHPMSPaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M

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

By formula: C7H6NO2- + H+ = C7H7NO2

Quantity Value Units Method Reference Comment
Deltar1518. ± 8.8kJ/molG+TSCaldwell and Bartmessgas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar1488. ± 8.4kJ/molIMRECaldwell and Bartmessgas phase; value altered from reference due to change in acidity scale; B

Henry's Law data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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: Rolf Sander

Henry's Law constant (water solution)

kH(T) = H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
H = Henry's law constant for solubility in water at 298.15 K (mol/kg*bar)
d(ln(kH))/d(1/T) = Temperature dependence constant (K)

H (mol/kg*bar) d(ln(kH))/d(1/T) (K) Method Reference
14.3200.XN/A
14. VN/A

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., 1986«DELTA»Gea(423 K) = -22.1 kcal/mol; «DELTA»Sea (estimated) = -1.7 eu.; B
0.984 ± 0.048IMREFukuda and McIver, 1985«DELTA»Gea(355 K) = -22.1 kcal/mol; «DELTA»Sea =-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
Deltar1518. ± 8.8kJ/molG+TSCaldwell and Bartmessgas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar1488. ± 8.4kJ/molIMRECaldwell and Bartmessgas phase; value altered from reference due to change in acidity scale; B

Ion clustering data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References, Notes

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

Data compiled as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

Bromine anion + Benzene, 1-methyl-3-nitro- = (Bromine anion bullet Benzene, 1-methyl-3-nitro-)

By formula: Br- + C7H7NO2 = (Br- bullet C7H7NO2)

Quantity Value Units Method Reference Comment
Deltar66.5 ± 7.5kJ/molIMREPaul and Kebarle, 1991gas phase; «DELTA»Gaff at 423 K, «DELTA»Saff taken as that of mCF3-nitrobenzene..Br-; B,M
Quantity Value Units Method Reference Comment
Deltar92.J/mol*KN/APaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar27. ± 4.2kJ/molIMREPaul and Kebarle, 1991gas phase; «DELTA»Gaff at 423 K, «DELTA»Saff taken as that of mCF3-nitrobenzene..Br-; B

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
26.423.PHPMSPaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M

IR Spectrum

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), UV/Visible spectrum, References, Notes

Data compiled by: Coblentz Society, Inc.

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


Mass spectrum (electron ionization)

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, UV/Visible spectrum, 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

Spectrum

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Mass 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 Japan AIST/NIMC Database- Spectrum MS-NW-2183
NIST MS number 228168

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


UV/Visible spectrum

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, 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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis spectrum
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Additional Data

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Source Lang (editor), 1965
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 19987
Instrument Unicam SP 500
Melting point oil

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Notes

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

Swarts, 1914
Swarts, F., Sur la chaleur de combustion de quelques derives nitres aromatlques, Recl. Trav. Chim. Pays-Bas, 1914, 33, 281-298. [all data]

Lenchitz, Velicky, et al., 1971
Lenchitz, C.; Velicky, R.W.; Silvestro, G.; Schlosberg, L.P., Thermodynamic properties of several nitrotoluenes, J. Chem. Thermodyn., 1971, 3, 689-692. [all data]

Garner and Abernethy, 1921
Garner, W.E.; Abernethy, C.L., Heats of combustion and formation of nitro-compounds. Part I. - Benzene, toluene, phenol and methylaniline series, Proc. Roy. Soc. London A, 1921, 213-235. [all data]

de Kolossowsky and Udowenko, 1934
de Kolossowsky, N.; Udowenko, W.W., Determination des chaleurs specifiques des liquides, Compt. rend., 1934, 198, 1394-1395. [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Lecat, 1930
Lecat, M., Azeotropism in Binary Mixtures Containing an Alcohol Mixed with an amine, a nitro derivative, an ether or water., Z. Anorg. Allg. Chem., 1930, 186, 119. [all data]

Dessart, 1926
Dessart, A., Theory of Concentrated Solutions: III. Physical Constants of Mixtures of m-Nitrotoluene and m-Toluidine with Some Hydrocarbons, Bull. Soc. Chim. Belg., 1926, 35, 9. [all data]

Gross, Saylor, et al., 1933
Gross, P.M.; Saylor, J.H.; Gorman, M.A., Solubility studies: IV the solubilities of certain slightly soluble organic compounds in water, J. Am. Chem. Soc., 1933, 55, 650-2. [all data]

Widegren and Bruno, 2010
Widegren, Jason A.; Bruno, Thomas J., Gas Saturation Vapor Pressure Measurements of Mononitrotoluene Isomers from (283.15 to 313.15) K «8224», J. Chem. Eng. Data, 2010, 55, 1, 159-164, https://doi.org/10.1021/je900293j . [all data]

Aim, 1994
Aim, Karel, Saturated Vapor Pressure Measurements on Isomeric Mononitrotoluenes at Temperatures between 380 and 460 K, J. Chem. Eng. Data, 1994, 39, 3, 591-594, https://doi.org/10.1021/je00015a044 . [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Paul and Kebarle, 1991
Paul, G.J.C.; Kebarle, P., Stabilities of Complexes of Br- with Substituted Benzenes (SB) Based on Determinations of the Gas-Phase Equilibria Br- + SB = (BrSB)-, J. Am. Chem. Soc., 1991, 113, 4, 1148, https://doi.org/10.1021/ja00004a014 . [all data]

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

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]

Lang (editor), 1965
Lang (editor), L., Absorption Spectra in the Ultraviolet and Visible Region, 1965, 6, 11. [all data]


Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References