Benzene, 1,4-difluoro-

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Gas 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
Δfgas-306.7 ± 1.0kJ/molCcrGood, Lacina, et al., 1962Corrected 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- + Hydrogen cation = Benzene, 1,4-difluoro-

By formula: C6H3F2- + H+ = C6H4F2

Quantity Value Units Method Reference Comment
Δr1591. ± 8.8kJ/molG+TSBuker, Nibbering, et al., 1997gas phase; B
Δr1589. ± 13.kJ/molG+TSBriscese and Riveros, 1975gas phase; < MeOH, <= EtOH; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr1557. ± 8.4kJ/molIMREBuker, Nibbering, et al., 1997gas phase; B
Δr1555. ± 13.kJ/molIMRBBriscese and Riveros, 1975gas phase; < MeOH, <= EtOH; value altered from reference due to change in acidity scale; B

NH4+ + Benzene, 1,4-difluoro- = (NH4+ • Benzene, 1,4-difluoro-)

By formula: H4N+ + C6H4F2 = (H4N+ • C6H4F2)

Quantity Value Units Method Reference Comment
Δr54.kJ/molPHPMSDeakyne and Meot-Ner (Mautner), 1985gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr84.J/mol*KN/ADeakyne and Meot-Ner (Mautner), 1985gas phase; Entropy change calculated or estimated; M

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
21.395.PHPMSDeakyne and Meot-Ner (Mautner), 1985gas phase; Entropy change calculated or estimated; M

Chlorine anion + Benzene, 1,4-difluoro- = (Chlorine anion • Benzene, 1,4-difluoro-)

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

Quantity Value Units Method Reference Comment
Δr57.7 ± 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
Δr31. ± 8.4kJ/molIMRELarson and McMahon, 1984gas phase; B,M

C6H6+ + Benzene, 1,4-difluoro- = (C6H6+ • Benzene, 1,4-difluoro-)

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

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Δr47.3kJ/molMPIErnstberger, Krause, et al., 1990gas phase; M

C6H4F2+ + Benzene, 1,4-difluoro- = (C6H4F2+ • Benzene, 1,4-difluoro-)

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

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Δr37.kJ/molMPIErnstberger, Krause, et al., 1990gas phase; M

Chromium ion (1+) + Benzene, 1,4-difluoro- = (Chromium ion (1+) • Benzene, 1,4-difluoro-)

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

Quantity Value Units Method Reference Comment
Δr121.kJ/molRAKRyzhov, 1999RCD

IR Spectrum

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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

Gas Phase Spectrum

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IR spectrum
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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 Sadtler Research Labs Under US-EPA Contract
State gas

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


Gas Chromatography

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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

Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
PackedSE-30666.Peng, Ding, et al., 1988He, Supelcoport and Chromosorb, 40. C @ 4. min, 10. K/min, 250. C @ 60. min; Column length: 3.05 m

Normal alkane RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryOV-101665.Zenkevich, 200525. m/0.20 mm/0.10 μm, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C

References

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, IR Spectrum, Gas Chromatography, 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]

Deakyne and Meot-Ner (Mautner), 1985
Deakyne, C.A.; Meot-Ner (Mautner), M., Unconventional Ionic Hydrogen Bonds. 2. NH+ pi. Complexes of Onium Ions with Olefins and Benzene Derivatives, J. Am. Chem. Soc., 1985, 107, 2, 474, https://doi.org/10.1021/ja00288a034 . [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]

Ernstberger, Krause, et al., 1990
Ernstberger, B.; Krause, H.; Kiermeier, A.; Neusser, H.J., Multiphoton ionization and dissociation of mixed van der Waals clusters in a linear reflectron time-of-flight mass spectrometer, J. Chem. Phys., 1990, 92, 9, 5285, https://doi.org/10.1063/1.458603 . [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]

Peng, Ding, et al., 1988
Peng, C.T.; Ding, S.F.; Hua, R.L.; Yang, Z.C., Prediction of Retention Indexes I. Structure-Retention Index Relationship on Apolar Columns, J. Chromatogr., 1988, 436, 137-172, https://doi.org/10.1016/S0021-9673(00)94575-8 . [all data]

Zenkevich, 2005
Zenkevich, I.G., Experimentally measured retention indices., 2005. [all data]


Notes

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