1,3,5-Trifluorobenzene
- Formula: C6H3F3
- Molecular weight: 132.0832
- IUPAC Standard InChIKey: JXUKFFRPLNTYIV-UHFFFAOYSA-N
- CAS Registry Number: 372-38-3
- 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: Benzene, 1,3,5-trifluoro-; sym-Trifluorobenzene
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Phase change data
Go To: Top, Reaction thermochemistry 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:
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 348.6 | K | N/A | PCR Inc., 1990 | BS |
Tboil | 348.7 | K | N/A | Weast and Grasselli, 1989 | BS |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 8.10 | kcal/mol | N/A | Boublik, Fried, et al., 1984 | Based on data from 280. to 320. K. See also Basarová and Svoboda, 1991.; AC |
ΔvapH° | 8.064 | kcal/mol | V | Findlay, 1969 | ALS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
8.25 | 294. | A,MM | Stephenson and Malanowski, 1987 | Based on data from 279. to 350. K. See also Findlay, 1969, 2 and Dykyj, 1972.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
279.33 to 323.14 | 4.03580 | 1195.549 | -54.196 | Findlay, 1969, 2 | Coefficents calculated by NIST from author's data. |
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:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
B - John E. Bartmess
RCD - Robert C. Dunbar
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: C6H6+ + C6H3F3 = (C6H6+ • C6H3F3)
Bond type: Charge transfer bond (positive ion)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 12.4 | kcal/mol | PHPMS | Meot-Ner (Mautner), Hamlet, et al., 1978 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 28. | cal/mol*K | PHPMS | Meot-Ner (Mautner), Hamlet, et al., 1978 | gas phase; M |
C6H2F3- + =
By formula: C6H2F3- + H+ = C6H3F3
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrG° | 361.4 ± 2.0 | kcal/mol | IMRE | Buker, Nibbering, et al., 1997 | gas phase; B |
By formula: Cr+ + C6H3F3 = (Cr+ • C6H3F3)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 26.3 | kcal/mol | RAK | Ryzhov, 1999 | RCD |
Gas phase ion energetics data
Go To: Top, Phase change data, Reaction thermochemistry 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 177.3 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 171.0 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.5 | PE | Maier and Thommen, 1981 | LLK |
9.64 | PE | Sell, Mintz, et al., 1978 | LLK |
9.64 | PE | Gilbert, Sauvageau, et al., 1972 | LLK |
9.3 | PI | Bralsford, Harris, et al., 1960 | RDSH |
9.26 | PE | Streets and Ceasar, 1973 | Vertical value; LLK |
De-protonation reactions
C6H2F3- + =
By formula: C6H2F3- + H+ = C6H3F3
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrG° | 361.4 ± 2.0 | kcal/mol | IMRE | Buker, Nibbering, et al., 1997 | gas phase; B |
Ion clustering data
Go To: Top, Phase change data, Reaction thermochemistry 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:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
RCD - Robert C. Dunbar
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: C6H6+ + C6H3F3 = (C6H6+ • C6H3F3)
Bond type: Charge transfer bond (positive ion)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 12.4 | kcal/mol | PHPMS | Meot-Ner (Mautner), Hamlet, et al., 1978 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 28. | cal/mol*K | PHPMS | Meot-Ner (Mautner), Hamlet, et al., 1978 | gas phase; M |
By formula: Cr+ + C6H3F3 = (Cr+ • C6H3F3)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 26.3 | kcal/mol | RAK | Ryzhov, 1999 | RCD |
IR Spectrum
Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Gas Phase Spectrum
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Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.
Additional Data
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Owner | NIST Standard Reference Data Program Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | NIST Mass Spectrometry Data Center |
State | gas |
Instrument | HP-GC/MS/IRD |
Mass spectrum (electron ionization)
Go To: Top, Phase change data, Reaction thermochemistry 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-IW-2588 |
NIST MS number | 236228 |
References
Go To: Top, Phase change data, Reaction thermochemistry 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.
PCR Inc., 1990
PCR Inc.,
Research Chemicals Catalog 1990-1991, PCR Inc., Gainesville, FL, 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]
Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E.,
The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]
Basarová and Svoboda, 1991
Basarová, Pavlína; Svoboda, Václav,
Calculation of heats of vaporization of halogenated hydrocarbons from saturated vapour pressure data,
Fluid Phase Equilibria, 1991, 68, 13-34, https://doi.org/10.1016/0378-3812(91)85008-I
. [all data]
Findlay, 1969
Findlay, T.J.V.,
Vapor pressures of fluorobenzenes from 5° to 50°C,
J. Chem. Eng. Data, 1969, 14, 229. [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]
Findlay, 1969, 2
Findlay, T.J.V.,
Vapor pressures of fluorobenzenes from 5 to 50.deg.C,
J. Chem. Eng. Data, 1969, 14, 2, 229-231, https://doi.org/10.1021/je60041a012
. [all data]
Dykyj, 1972
Dykyj, J.,
Petrochemia, 1972, 12, 1, 13. [all data]
Meot-Ner (Mautner), Hamlet, et al., 1978
Meot-Ner (Mautner), M.; Hamlet, P.; Hunter, E.P.; Field, F.H.,
Bonding Energies in Association Ions of Aromatic Molecules. Correlations with Ionization Energies,
J. Am. Chem. Soc., 1978, 100, 17, 5466, https://doi.org/10.1021/ja00485a034
. [all data]
Buker, Nibbering, et al., 1997
Buker, H.H.; Nibbering, N.M.M.; Espinosa, D.; Mongin, F.; Schlosser, M.,
Additivity of substituent effects in the fluoroarene series: Equilibrium acidity in the gas phase and deprotonation rates in ethereal solution,
Tetrahed. Lett., 1997, 38, 49, 8519-8522, https://doi.org/10.1016/S0040-4039(97)10303-3
. [all data]
Ryzhov, 1999
Ryzhov, V.,
Binding Energies of Chromium Cations with Fluorobenzenes from Radiative Association Kinetics,
Int. J. Mass Spectrom., 1999, 185/186/187, 913. [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]
Maier and Thommen, 1981
Maier, J.P.; Thommen, F.,
Fluorescence quantum yields and lifetimes of fluorobenzene cations in selected levels of their B and C states determined by photoelectron-photoion coincidence spectroscopy,
Chem. Phys., 1981, 57, 319. [all data]
Sell, Mintz, et al., 1978
Sell, J.A.; Mintz, D.M.; Kupperman, A.,
Photoelectron angular distributions of carbon-carbon π electrons in ethylene, benzene, and their fluorinated derivatives,
Chem. Phys. Lett., 1978, 58, 601. [all data]
Gilbert, Sauvageau, et al., 1972
Gilbert, R.; Sauvageau, P.; Sandorfy, C.,
Far-UV and photoelectron spectra of 1,3,5-trifluorobenzene,
Chem. Phys. Lett., 1972, 17, 465. [all data]
Bralsford, Harris, et al., 1960
Bralsford, R.; Harris, P.V.; Price, W.C.,
The effect of fluorine on the electronic spectra and ionization potentials of molecules,
Proc. Roy. Soc. (London), 1960, A258, 459. [all data]
Streets and Ceasar, 1973
Streets, D.G.; Ceasar, G.P.,
Inductive mesomeric effects on the π orbitals of halobenzenes,
Mol. Phys., 1973, 26, 1037. [all data]
Notes
Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), References
- Symbols used in this document:
Tboil Boiling point 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 ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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