Benzene, 1,3,5-trimethyl-2-nitro-
- Formula: C9H11NO2
- Molecular weight: 165.1891
- IUPAC Standard InChIKey: SCEKDQTVGHRSNS-UHFFFAOYSA-N
- CAS Registry Number: 603-71-4
- Chemical structure:
This structure is also available as a 2d Mol file - Other names: Mesitylene, 2-nitro-; Mononitromesitylene; Nitromesitylene; 2-Nitromesitylene; 2,4,6-Trimethyl-1-nitrobenzene; 2,4,6-Trimethylnitrobenzene; 1,3,5-Trimethyl-2-nitrobenzene; NSC 5413
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Gas phase 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -6.41 ± 0.53 | kcal/mol | Ccb | Acree, Tucker, et al., 1993 |
Condensed phase 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°solid | -25.19 ± 0.48 | kcal/mol | Ccb | Acree, Tucker, et al., 1993 | crystal phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -1197.0 ± 0.38 | kcal/mol | Ccb | Acree, Tucker, et al., 1993 | crystal phase |
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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 528.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 317. | K | N/A | White, Biggs, et al., 1940 | Uncertainty assigned by TRC = 1.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 18.8 ± 0.24 | kcal/mol | C | Acree, Tucker, et al., 1993 | crystal phase; ALS |
ΔsubH° | 18.8 ± 0.24 | kcal/mol | C | Acree, Tucker, et al., 1993 | See also Acree, Tucker, et al., 1993.; AC |
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
Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
B - John E. Bartmess
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 196.9 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 189.6 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
0.70 ± 0.10 | IMRE | Mishima, Kang, et al., 1993 | ΔGea(343 K) = -15.5 kcal/mol; ΔSea (est) = -2.0 eu.; B |
0.71 ± 0.10 | TDEq | Chowdhury, Heinis, et al., 1986 | ΔGea= -16.1 kcal/mol; ΔSea estimated = -1.1 eu.; B |
0.707 ± 0.087 | IMRE | Huh, Kang, et al., 1999 | ΔG(EA) 343K; anchored to ΔG value. Including anchor ΔS, EA is ca. 0.4 kcal/mol more bound.; B |
0.776 ± 0.048 | IMRE | Fukuda and McIver, 1985 | ΔGea(355 K) = -17.5 kcal/mol; ΔSea =-1.1, est. from data in Chowdhury, Heinis, et al., 1986; B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.8 | PE | Kobayashi and Nagakura, 1974 | LLK |
9.01 | PE | Kobayashi and Nagakura, 1974 | Vertical value; LLK |
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 | Japan AIST/NIMC Database- Spectrum MS-NW-8743 |
NIST MS number | 238456 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, 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.
Acree, Tucker, et al., 1993
Acree, W.E., Jr.; Tucker, S.A.; Pilcher, G.; Chowdhary, A.; Ribeiro da Silva, M.D.M.; Monte, M.J.S.,
Enthalpies of combustion of 2,2',4,4',6,6'-hexamethylazobenzene-N,N-dioxide, 2,2',6,6'-tetramethylazobenzene-N,N-dioxide, 2,4,6-trimethylnitrobenzene, and 2,6-dimethyl-nitrobenzene: the dissociation enthalpies of the N=N and N-O bonds,
J. Chem. Thermodyn., 1993, 25, 1253-1261. [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]
White, Biggs, et al., 1940
White, A.H.; Biggs, B.S.; Morgan, S.O.,
Dielectric Evidence for Molecular Rotation in the Crystals of Certain Benzene Derivatives,
J. Am. Chem. Soc., 1940, 62, 16-25. [all data]
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]
Mishima, Kang, et al., 1993
Mishima, M.; Kang, C.H.; Huh, C.; Fujio, M.; Tsuno, Y.,
Substituent Effect on Electron Affinity of 2,6-Dimethylnitrobenzene,
Chem. Lett., 1993, 22, 5, 889, https://doi.org/10.1246/cl.1993.889
. [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]
Huh, Kang, et al., 1999
Huh, C.; Kang, C.H.; Lee, H.W.; Nakamura, H.; Mishima, M.; Tsuno, Y.; Yamataka, H.,
Thermodynamic stabilities and resonance demand of aromatic radical anions in the gas phase,
Bull. Chem. Soc. Japan, 1999, 72, 5, 1083-1091, https://doi.org/10.1246/bcsj.72.1083
. [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]
Kobayashi and Nagakura, 1974
Kobayashi, T.; Nagakura, S.,
Photoelectron spectra of substituted benzenes,
Bull. Chem. Soc. Jpn., 1974, 47, 2563. [all data]
Notes
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- Symbols used in this document:
EA Electron affinity Tboil Boiling point Tfus Fusion (melting) point ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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