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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
Deltafgas-73.30 ± 0.25kcal/molCcrGood, Lacina, et al., 1962Corrected for CODATA value of «DELTA»fH

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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Deltafliquid-81.81 ± 0.25kcal/molCcrGood, Lacina, et al., 1962Corrected for CODATA value of «DELTA»fH; ALS
Quantity Value Units Method Reference Comment
Deltacliquid-704.68 ± 0.13kcal/molCcrGood, Lacina, et al., 1962Corrected for CODATA value of «DELTA»fH; ALS
Deltacliquid-706.1kcal/molCcbSwarts, 1919Not corrected for CODATA value of «DELTA»fH; ALS

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
38.03298.15Lichanot, 1991T = 186 to 324 K. Cp(liq) = 155.192 + 0.158T(°C) J/mol*K (-35 to 51°C). Cp value calculated from equation.; DH
37.64298.15Good, Lacina, et al., 1962DH

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, 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, 1,4-difluoro-

By formula: C6H3F2- + H+ = C6H4F2

Quantity Value Units Method Reference Comment
Deltar380.2 ± 2.1kcal/molG+TSBuker, Nibbering, et al., 1997gas phase; B
Deltar379.8 ± 3.1kcal/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
Deltar372.1 ± 2.0kcal/molIMREBuker, Nibbering, et al., 1997gas phase; B
Deltar371.7 ± 3.0kcal/molIMRBBriscese and Riveros, 1975gas phase; < MeOH, <= EtOH; value altered from reference due to change in acidity scale; B

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

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

Quantity Value Units Method Reference Comment
Deltar13.kcal/molPHPMSDeakyne and Meot-Ner (Mautner), 1985gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar20.cal/mol*KN/ADeakyne and Meot-Ner (Mautner), 1985gas phase; Entropy change calculated or estimated; M

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
5.1395.PHPMSDeakyne and Meot-Ner (Mautner), 1985gas phase; Entropy change calculated or estimated; M

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

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

Quantity Value Units Method Reference Comment
Deltar13.8 ± 2.0kcal/molIMRELarson and McMahon, 1984gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar21.6cal/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
Deltar7.3 ± 2.0kcal/molIMRELarson and McMahon, 1984gas phase; B,M

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

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

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar11.3kcal/molMPIErnstberger, Krause, et al., 1990gas phase; M

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

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

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar8.8kcal/molMPIErnstberger, Krause, et al., 1990gas phase; M

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

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

Quantity Value Units Method Reference Comment
Deltar29.0kcal/molRAKRyzhov, 1999RCD

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, 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]

Swarts, 1919
Swarts, F., Etudes thermochimiques sur les combinaisons organiques fluorees, J. Chim. Phys., 1919, 17, 3-70. [all data]

Lichanot, 1991
Lichanot, A., Heat capacities of fluroaniline, fluorophenol and difluorobenzene in condensed phase, Thermochim. Acta, 1991, 177, 265-272. [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]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References