Benzene, 1,3-difluoro-
- Formula: C6H4F2
- Molecular weight: 114.0928
- IUPAC Standard InChIKey: UEMGWPRHOOEKTA-UHFFFAOYSA-N
- CAS Registry Number: 372-18-9
- 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, m-difluoro-; m-Difluorobenzene; 1,3-Difluorobenzene; meta-Difluorobenzene
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Gas phase thermochemistry data
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -309.2 ± 1.0 | kJ/mol | Ccr | Good, Lacina, et al., 1962 | Corrected for CODATA value of ΔfH |
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
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
C6H3F2- + =
By formula: C6H3F2- + H+ = C6H4F2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1565. ± 8.8 | kJ/mol | G+TS | Buker, Nibbering, et al., 1997 | gas phase; B |
ΔrH° | <1575.5 ± 1.3 | kJ/mol | G+TS | Briscese and Riveros, 1975 | gas phase; < iPrOH; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1533. ± 8.4 | kJ/mol | IMRE | Buker, Nibbering, et al., 1997 | gas phase; B |
ΔrG° | <1543.1 | kJ/mol | IMRB | Briscese and Riveros, 1975 | gas phase; < iPrOH; value altered from reference due to change in acidity scale; B |
By formula: Cl- + C6H4F2 = (Cl- • C6H4F2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 61.1 ± 8.4 | kJ/mol | IMRE | Larson and McMahon, 1984 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 94.6 | J/mol*K | N/A | Larson and McMahon, 1984 | gas phase; switching reaction(Cl-)ClCOOCH3, Entropy change calculated or estimated; Larson and McMahon, 1984, 2; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 33. ± 8.4 | kJ/mol | IMRE | Larson and McMahon, 1984 | gas phase; B,M |
ΔrG° | 32. ± 4.2 | kJ/mol | TDEq | French, Ikuta, et al., 1982 | gas phase; B |
By formula: C6H4F2+ + C6H4F2 = (C6H4F2+ • C6H4F2)
Bond type: Charge transfer bond (positive ion)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 55.2 | kJ/mol | PHPMS | Meot-Ner (Mautner), Hamlet, et al., 1978 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 110. | J/mol*K | N/A | Meot-Ner (Mautner), Hamlet, et al., 1978 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 22. | kJ/mol | PHPMS | Meot-Ner (Mautner), Hamlet, et al., 1978 | gas phase; Entropy change calculated or estimated; M |
By formula: C6H6+ + C6H4F2 = (C6H6+ • C6H4F2)
Bond type: Charge transfer bond (positive ion)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 58.2 | kJ/mol | PHPMS | Meot-Ner (Mautner), Hamlet, et al., 1978 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 110. | J/mol*K | PHPMS | Meot-Ner (Mautner), Hamlet, et al., 1978 | gas phase; M |
By formula: Cr+ + C6H4F2 = (Cr+ • C6H4F2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 134. | kJ/mol | RAK | Ryzhov, 1999 | RCD |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - 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 |
---|---|---|---|---|---|
IE (evaluated) | 9.33 ± 0.02 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 749.7 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 722. | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.2 | PE | Maier and Thommen, 1981 | LLK |
9.332 ± 0.004 | EQ | Lias and Ausloos, 1978 | LLK |
9.35 | S | Gilbert and Sandorfy, 1974 | LLK |
9.78 ± 0.02 | EI | Momigny and Wirtz-Cordier, 1962 | RDSH |
9.32 | PE | Streets and Ceasar, 1973 | Vertical value; LLK |
9.6 ± 0.03 | PE | Klessinger, 1972 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C4H2F2+ | 15.30 | C2H2 | EI | Momigny and Wirtz-Cordier, 1962 | RDSH |
De-protonation reactions
C6H3F2- + =
By formula: C6H3F2- + H+ = C6H4F2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1565. ± 8.8 | kJ/mol | G+TS | Buker, Nibbering, et al., 1997 | gas phase; B |
ΔrH° | <1575.5 ± 1.3 | kJ/mol | G+TS | Briscese and Riveros, 1975 | gas phase; < iPrOH; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1533. ± 8.4 | kJ/mol | IMRE | Buker, Nibbering, et al., 1997 | gas phase; B |
ΔrG° | <1543.1 | kJ/mol | IMRB | Briscese and Riveros, 1975 | gas phase; < iPrOH; value altered from reference due to change in acidity scale; B |
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-5902 |
NIST MS number | 230724 |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry 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.
Good, Lacina, et al., 1962
Good, W.D.; Lacina, J.L.; Scott, D.W.; McCullough, J.P.,
Combustion calorimetry of organic fluorine compounds. The heats of combustion and formation of the difluorobenzenes, 4-fluorotoluene and m-trifluorotoluic acid,
J. Phys. Chem., 1962, 66, 1529-1532. [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]
Briscese and Riveros, 1975
Briscese, S.M.J.; Riveros, J.M.,
Gas phase nucleophilic reactions of aromatic systems,
J. Am. Chem. Soc., 1975, 97, 230. [all data]
Larson and McMahon, 1984
Larson, J.W.; McMahon, T.B.,
Hydrogen bonding in gas phase anions. An experimental investigation of the interaction between chloride ion and bronsted acids from ICR chloride exchange equilibria,
J. Am. Chem. Soc., 1984, 106, 517. [all data]
Larson and McMahon, 1984, 2
Larson, J.W.; McMahon, T.B.,
Gas phase negative ion chemistry of alkylchloroformates,
Can. J. Chem., 1984, 62, 675. [all data]
French, Ikuta, et al., 1982
French, M.A.; Ikuta, S.; Kebarle, P.,
Hydrogen bonding of O-H and C-H hydrogen donors to Cl-. Results from mass spectrometric measurement of the ion-molecule equilibria RH + Cl- = RHCl-,
Can. J. Chem., 1982, 60, 1907. [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]
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]
Lias and Ausloos, 1978
Lias, S.G.; Ausloos, P.J.,
eIonization energies of organic compounds by equilibrium measurements,
J. Am. Chem. Soc., 1978, 100, 6027. [all data]
Gilbert and Sandorfy, 1974
Gilbert, R.; Sandorfy, C.,
Rydberg transitions in the ultraviolet spectra of difluorobenzenes,
Chem. Phys. Lett., 1974, 27, 457. [all data]
Momigny and Wirtz-Cordier, 1962
Momigny, J.; Wirtz-Cordier, A.M.,
Les effets de l'impact electronique sur des derives dihalogenes du benzene,
Ann. Soc. Sci. Bruxelles, 1962, 76, 164. [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]
Klessinger, 1972
Klessinger, M.,
Ionization potentials of substituted benzenes,
Angew. Chem. Int. Ed. Engl., 1972, 11, 525. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy ΔfH°gas Enthalpy of formation of gas 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 - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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