Benzene, 1-nitro-3-(trifluoromethyl)-
- Formula: C7H4F3NO2
- Molecular weight: 191.1074
- IUPAC Standard InChI: InChI=1S/C7H4F3NO2/c8-7(9,10)5-2-1-3-6(4-5)11(12)13/h1-4H
- IUPAC Standard InChIKey: WHNAMGUAXHGCHH-UHFFFAOYSA-N
- CAS Registry Number: 98-46-4
- 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, α,α,α-trifluoro-m-nitro-; α,α,α-Trifluoro-m-nitrotoluene; m-(Trifluoromethyl)nitrobenzene; m-Nitrobenzotrifluoride; 1-Nitro-3-(trifluoromethyl)benzene; 3-(Trifluoromethyl)nitrobenzene; 3-Nitrobenzotrifluoride; m-Nitrotrifluorotoluene; 3-Nitro-α,α,α-trifluorotoluene; α,α,α-Trifluoro-3-nitrotoluene; m-Nitrotrifluortoluol; Toluene, 3-nitro-α,α,α-trifluoro-; USAF MA-5; 1,3-Nitrobenzotrifluoride; m-Nitro-α,α,α-trifluorotoluene; NSC 10313; Benzene, 1-trifluoromethyl-3-nitro
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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 |
|---|---|---|---|---|---|
| ΔcH°liquid | -771.5 | kcal/mol | Ccb | Swarts, 1919 | Not corrected for CODATA value of ΔfH |
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
AC - William E. Acree, Jr., James S. Chickos
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tboil | 475.7 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Enthalpy of vaporization
| ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 12.9 | 356. | A | Stephenson and Malanowski, 1987 | Based on data from 341. to 475. K. See also Kardon and Saylor, 1953 and Dykyj, Svoboda, et al., 1999.; 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- + C7H4F3NO2 = (Br- • C7H4F3NO2)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 18.5 ± 1.8 | kcal/mol | TDAs | Paul and Kebarle, 1991 | gas phase; ΔGaff at 423 K; B,M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 22.3 | cal/mol*K | PHPMS | Paul and Kebarle, 1991 | gas phase; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 9.1 ± 1.0 | kcal/mol | TDAs | Paul and Kebarle, 1991 | gas phase; ΔGaff at 423 K; B |
+
= (
•
)
By formula: Cl- + C7H4F3NO2 = (Cl- • C7H4F3NO2)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 19.5 ± 1.0 | kcal/mol | TDAs | Chowdhury and Kebarle, 1986 | gas phase; B,M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 17.9 | cal/mol*K | PHPMS | Chowdhury and Kebarle, 1986 | gas phase; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 14.1 ± 1.6 | kcal/mol | TDAs | Chowdhury and Kebarle, 1986 | gas phase; B |
By formula: F6S- + C7H4F3NO2 = (F6S- • C7H4F3NO2)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 17.0 ± 1.0 | kcal/mol | TDAs | Chowdhury and Kebarle, 1986 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 9.0 ± 1.6 | kcal/mol | TDAs | Chowdhury and Kebarle, 1986 | gas phase; B |
By formula: F6S- + C7H4F3NO2 = (F6S- • C7H4F3NO2)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 17.0 | kcal/mol | PHPMS | Chowdhury and Kebarle, 1986 | gas phase; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 26.7 | cal/mol*K | PHPMS | Chowdhury and Kebarle, 1986 | gas phase; M |
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 compiled by: John E. Bartmess
Electron affinity determinations
| EA (eV) | Method | Reference | Comment |
|---|---|---|---|
| 1.41 ± 0.10 | TDEq | Chowdhury, Heinis, et al., 1986 | ΔGea(423 K) = -31.6 kcal/mol, ΔS = -2.5 eu |
| 1.370 ± 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. |
| <1.410 ± 0.050 | PD | Mock and Grimsrud, 1989 | |
| 1.405 ± 0.048 | IMRE | Fukuda and McIver, 1985 | ΔGea(355 K) = -31.5 kcal/mol; ΔSea =-2.5, est. from data in Chowdhury, Heinis, et al., 1986 |
Ion clustering 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. Searches may be limited to ion clustering reactions. A general reaction search form is also available.
Clustering reactions
+
= (
•
)
By formula: Br- + C7H4F3NO2 = (Br- • C7H4F3NO2)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 18.5 ± 1.8 | kcal/mol | TDAs | Paul and Kebarle, 1991 | gas phase; ΔGaff at 423 K; B,M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 22.3 | cal/mol*K | PHPMS | Paul and Kebarle, 1991 | gas phase; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 9.1 ± 1.0 | kcal/mol | TDAs | Paul and Kebarle, 1991 | gas phase; ΔGaff at 423 K; B |
+
= (
•
)
By formula: Cl- + C7H4F3NO2 = (Cl- • C7H4F3NO2)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 19.5 ± 1.0 | kcal/mol | TDAs | Chowdhury and Kebarle, 1986 | gas phase; B,M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 17.9 | cal/mol*K | PHPMS | Chowdhury and Kebarle, 1986 | gas phase; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 14.1 ± 1.6 | kcal/mol | TDAs | Chowdhury and Kebarle, 1986 | gas phase; B |
By formula: F6S- + C7H4F3NO2 = (F6S- • C7H4F3NO2)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 17.0 ± 1.0 | kcal/mol | TDAs | Chowdhury and Kebarle, 1986 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 9.0 ± 1.6 | kcal/mol | TDAs | Chowdhury and Kebarle, 1986 | gas phase; B |
By formula: F6S- + C7H4F3NO2 = (F6S- • C7H4F3NO2)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 17.0 | kcal/mol | PHPMS | Chowdhury and Kebarle, 1986 | gas phase; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 26.7 | cal/mol*K | PHPMS | Chowdhury and Kebarle, 1986 | gas phase; M |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Swarts, 1919
Swarts, F.,
Etudes thermochimiques sur les combinaisons organiques fluorees,
J. Chim. Phys., 1919, 17, 3-70. [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]
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]
Kardon and Saylor, 1953
Kardon, Samuel; Saylor, John H.,
The Vapor Pressures of Some Substituted Benzotrifluorides 1,
J. Am. Chem. Soc., 1953, 75, 8, 1997-1997, https://doi.org/10.1021/ja01104a512
. [all data]
Dykyj, Svoboda, et al., 1999
Dykyj, J.; Svoboda, J.; Wilhoit, R.C.; Frenkel, M.L.; Hall, K.R.,
Vapor Pressure of Chemicals: Part A. Vapor Pressure and Antoine Constants for Hydrocarbons and Sulfur, Selenium, Tellurium and Hydrogen Containing Organic Compounds, Springer, Berlin, 1999, 373. [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]
Chowdhury and Kebarle, 1986
Chowdhury, S.; Kebarle, P.,
Role of Binding Energies in A-.B and A.B- Complexes in the Kinetics of Gas Phase Electron Transfer Reactions:A- + B = A + B- Involving Perfluoro Compounds: SF6, C6F11CF3,
J. Chem. Phys., 1986, 85, 9, 4989, https://doi.org/10.1063/1.451687
. [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]
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]
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]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, References
- Symbols used in this document:
EA Electron affinity Tboil Boiling point ΔcH°liquid Enthalpy of combustion 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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