Benzene, 1,3,5-trimethyl-2-nitro-
- Formula: C9H11NO2
- Molecular weight: 165.1891
- IUPAC Standard InChI: InChI=1S/C9H11NO2/c1-6-4-7(2)9(10(11)12)8(3)5-6/h4-5H,1-3H3
- 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 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) | 823.8 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
| Quantity | Value | Units | Method | Reference | Comment |
| Gas basicity | 793.1 | kJ/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 |
References
Go To: Top, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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
Go To: Top, Gas phase ion energetics data, References
- Symbols used in this document:
EA Electron affinity - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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