Benzene, 1-methyl-3-nitro-
- Formula: C7H7NO2
- Molecular weight: 137.1360
- IUPAC Standard InChIKey: QZYHIOPPLUPUJF-UHFFFAOYSA-N
- CAS Registry Number: 99-08-1
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: Toluene, m-nitro-; m-Methylnitrobenzene; m-Nitrotoluene; MNT; 1-Methyl-3-nitrobenzene; 3-Nitrotoluene; 3-Methylnitrobenzene; 3-Nitrotoluol; UN 1664; 3-Methyl-1-nitrobenzene
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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), 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 |
---|---|---|---|---|---|
ΔfH°liquid | -46.0 | kJ/mol | Ccb | Swarts, 1914 | See 14SWA2; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -3723.5 ± 3.3 | kJ/mol | Ccb | Lenchitz, Velicky, et al., 1971 | ALS |
ΔcH°liquid | -3737. | kJ/mol | Ccb | Garner and Abernethy, 1921 | ALS |
ΔcH°liquid | -3721.9 | kJ/mol | Ccb | Swarts, 1914 | See 14SWA2; ALS |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
202.1 | 302.4 | de Kolossowsky and Udowenko, 1934 | DH |
Phase change 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 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 |
---|---|---|---|---|---|
Tboil | 503.7 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 505.8 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 503.95 | K | N/A | Lecat, 1930 | Uncertainty assigned by TRC = 0.4 K; not clear that this is a new measurement; TRC |
Tboil | 504. | K | N/A | Dessart, 1926 | Uncertainty assigned by TRC = 0.4 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 288.59 | K | N/A | Gross, Saylor, et al., 1933 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tfus | 289. | K | N/A | Dessart, 1926 | Uncertainty assigned by TRC = 2. K; TRC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
56.6 ± 2.5 | 303. | GS | Widegren and Bruno, 2010 | Based on data from 293. to 313. K.; AC |
52.8 | 413. | EB | Aim, 1994 | Based on data from 397. to 452. K.; AC |
49.8 | 368. | A | Stephenson and Malanowski, 1987 | Based on data from 353. to 505. K.; AC |
Reaction thermochemistry 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 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
By formula: Br- + C7H7NO2 = (Br- • C7H7NO2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 66.5 ± 7.5 | kJ/mol | IMRE | Paul and Kebarle, 1991 | gas phase; ΔGaff at 423 K, ΔSaff taken as that of mCF3-nitrobenzene..Br-; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 92. | J/mol*K | N/A | Paul and Kebarle, 1991 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 27. ± 4.2 | kJ/mol | IMRE | Paul and Kebarle, 1991 | gas phase; ΔGaff at 423 K, ΔSaff taken as that of mCF3-nitrobenzene..Br-; B |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
26. | 423. | PHPMS | Paul and Kebarle, 1991 | gas phase; Entropy change calculated or estimated; M |
C7H6NO2- + =
By formula: C7H6NO2- + H+ = C7H7NO2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1518. ± 8.8 | kJ/mol | G+TS | Caldwell and Bartmess | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1488. ± 8.4 | kJ/mol | IMRE | Caldwell and Bartmess | gas phase; value altered from reference due to change in acidity scale; B |
Henry's Law 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 compiled by: Rolf Sander
Henry's Law constant (water solution)
kH(T) = k°H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
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)
k°H (mol/(kg*bar)) | d(ln(kH))/d(1/T) (K) | Method | Reference |
---|---|---|---|
14. | 3200. | X | N/A |
14. | V | N/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 ± 0.1 | eV | N/A | N/A | L |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
0.99 ± 0.10 | IMRE | Chowdhury, Heinis, et al., 1986 | ΔGea(423 K) = -22.1 kcal/mol; ΔSea (estimated) = -1.7 eu.; B |
0.984 ± 0.048 | IMRE | Fukuda and McIver, 1985 | ΔGea(355 K) = -22.1 kcal/mol; ΔSea =-1.7, est. from data in Chowdhury, Heinis, et al., 1986; B |
0.970 ± 0.030 | ECD | Chen, Chen, et al., 1992 | B |
0.927993 | IMRB | Han and Brauman, 1988 | B |
<1.180 ± 0.050 | PD | Mock and Grimsrud, 1989 | B |
0.80 ± 0.10 | ECD | Zlatkis, Lee, et al., 1983 | B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.5 ± 0.1 | PIPECO | Baer, Morrow, et al., 1988 | LL |
9.50 | PE | Palmer, Moyes, et al., 1979 | LLK |
9.5 ± 0.1 | EI | Brown, 1970 | RDSH |
9.65 ± 0.05 | EI | Pignataro, Foffani, et al., 1966 | RDSH |
9.48 | PE | Kobayashi and Nagakura, 1974 | Vertical value; LLK |
9.49 ± 0.015 | PE | Kobayashi and Nagakura, 1972 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C5H5+ | 15.2 ± 0.2 | C2H2+NO2 | EI | Tajima and Tsuchiya, 1973 | LLK |
C7H7+ | 11.01 | NO2 | PIPECO | Baer, Morrow, et al., 1988 | T = 0K; LL |
C7H7+ | 11.08 | NO2 | PIPECO | Baer, Morrow, et al., 1988 | T = 298K; LL |
C7H7+ | 12.1 ± 0.3 | NO2 | EI | McLafferty and Winkler, 1974 | LLK |
C7H7+ | 11.6 ± 0.1 | NO2 | EI | Brown, 1970 | RDSH |
C7H7O+ | 10. ± 0.1 | NO | EI | Brown, 1970 | RDSH |
De-protonation reactions
C7H6NO2- + =
By formula: C7H6NO2- + H+ = C7H7NO2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1518. ± 8.8 | kJ/mol | G+TS | Caldwell and Bartmess | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1488. ± 8.4 | kJ/mol | IMRE | Caldwell and Bartmess | gas 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), 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
By formula: Br- + C7H7NO2 = (Br- • C7H7NO2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 66.5 ± 7.5 | kJ/mol | IMRE | Paul and Kebarle, 1991 | gas phase; ΔGaff at 423 K, ΔSaff taken as that of mCF3-nitrobenzene..Br-; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 92. | J/mol*K | N/A | Paul and Kebarle, 1991 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 27. ± 4.2 | kJ/mol | IMRE | Paul and Kebarle, 1991 | gas phase; ΔGaff at 423 K, ΔSaff taken as that of mCF3-nitrobenzene..Br-; B |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
26. | 423. | PHPMS | Paul and Kebarle, 1991 | gas 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), References, Notes
Data compiled by: Coblentz Society, Inc.
- LIQUID; Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY; 4 cm-1 resolution
- SOLUTION (10% CCl4 FOR 3800-1330, 10% CS2 FOR 1330-400 CM-1); DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY; 2 cm-1 resolution
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, 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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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
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 |
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), 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]
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), References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid EA Electron affinity IE (evaluated) Recommended ionization energy T Temperature Tboil Boiling point Tfus Fusion (melting) point d(ln(kH))/d(1/T) Temperature dependence parameter for Henry's Law constant k°H Henry's Law constant at 298.15K ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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