Benzene, 1,2-difluoro-

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Reaction thermochemistry data

Go To: Top, Henry's Law 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 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- + Hydrogen cation = Benzene, 1,2-difluoro-

By formula: C6H3F2- + H+ = C6H4F2

Quantity Value Units Method Reference Comment
Δr1580. ± 9.2kJ/molG+TSBuker, Nibbering, et al., 1997gas phase; B
Δr1582. ± 13.kJ/molG+TSBriscese and Riveros, 1975gas phase; Between EtO-, iPrO-; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr1546. ± 8.4kJ/molIMREBuker, Nibbering, et al., 1997gas phase; B
Δr1547. ± 13.kJ/molIMRBBriscese and Riveros, 1975gas phase; Between EtO-, iPrO-; value altered from reference due to change in acidity scale; B

C6H6+ + Benzene, 1,2-difluoro- = (C6H6+ • Benzene, 1,2-difluoro-)

By formula: C6H6+ + C6H4F2 = (C6H6+ • C6H4F2)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Δr63.6kJ/molPHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr110.J/mol*KN/AMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; Entropy change calculated or estimated; M

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
26.330.PHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; Entropy change calculated or estimated; M

Chlorine anion + Benzene, 1,2-difluoro- = (Chlorine anion • Benzene, 1,2-difluoro-)

By formula: Cl- + C6H4F2 = (Cl- • C6H4F2)

Quantity Value Units Method Reference Comment
Δr59.8 ± 8.4kJ/molIMRELarson and McMahon, 1984gas phase; B,M
Quantity Value Units Method Reference Comment
Δr90.4J/mol*KN/ALarson and McMahon, 1984gas phase; switching reaction(Cl-)ClCOOCH3, Entropy change calculated or estimated; Larson and McMahon, 1984, 2; M
Quantity Value Units Method Reference Comment
Δr33. ± 8.4kJ/molIMRELarson and McMahon, 1984gas phase; B,M

Chromium ion (1+) + Benzene, 1,2-difluoro- = (Chromium ion (1+) • Benzene, 1,2-difluoro-)

By formula: Cr+ + C6H4F2 = (Cr+ • C6H4F2)

Quantity Value Units Method Reference Comment
Δr138.kJ/molRAKRyzhov, 1999RCD

Henry's Law 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: Rolf Sander

Henry's Law constant (water solution)

kH(T) = H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(kH))/d(1/T) = Temperature dependence constant (K)

H (mol/(kg*bar)) d(ln(kH))/d(1/T) (K) Method Reference Comment
0.14 QN/A missing citation give several references for the Henry's law constants but don't assign them to specific species.

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
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)9.29 ± 0.01eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)731.2kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity703.5kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
9.284 ± 0.008EQLias and Ausloos, 1978LLK
9.30SGilbert and Sandorfy, 1974LLK
9.74 ± 0.02EIMomigny and Wirtz-Cordier, 1962RDSH
9.31PIBralsford, Harris, et al., 1960RDSH
9.30PEStreets and Ceasar, 1973Vertical value; LLK
9.6 ± 0.03PEKlessinger, 1972Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C4H2F2+15.27C2H2EIMomigny and Wirtz-Cordier, 1962RDSH

De-protonation reactions

C6H3F2- + Hydrogen cation = Benzene, 1,2-difluoro-

By formula: C6H3F2- + H+ = C6H4F2

Quantity Value Units Method Reference Comment
Δr1580. ± 9.2kJ/molG+TSBuker, Nibbering, et al., 1997gas phase; B
Δr1582. ± 13.kJ/molG+TSBriscese and Riveros, 1975gas phase; Between EtO-, iPrO-; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr1546. ± 8.4kJ/molIMREBuker, Nibbering, et al., 1997gas phase; B
Δr1547. ± 13.kJ/molIMRBBriscese and Riveros, 1975gas phase; Between EtO-, iPrO-; 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-9256
NIST MS number 230727

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References

Go To: Top, Reaction thermochemistry data, Henry's Law 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.

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]

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]

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]

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]

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]

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]

Klessinger, 1972
Klessinger, M., Ionization potentials of substituted benzenes, Angew. Chem. Int. Ed. Engl., 1972, 11, 525. [all data]


Notes

Go To: Top, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Mass spectrum (electron ionization), References