Benzene, fluoro-

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Condensed phase thermochemistry data

Go To: Top, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible 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 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
Δfliquid-150.8 ± 1.4kJ/molCcrGood, Scott, et al., 1956Corrected for CODATA value of ΔfH; ALS
Quantity Value Units Method Reference Comment
Δcliquid-3103.9 ± 1.2kJ/molCcrGood, Scott, et al., 1956Corrected for CODATA value of ΔfH; ALS
Δcliquid-3126.kJ/molCcbSwarts, 1919Not corrected for CODATA value of ΔfH; ALS
Quantity Value Units Method Reference Comment
liquid205.94J/mol*KN/AScott, McCullough, et al., 1956DH
liquid195.0J/mol*KN/AStull, 1937Extrapolation below 91 K, 42.55 J/mol*K.; DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
146.29298.15Roux, Grolier, et al., 1984DH
146.36298.15Scott, McCullough, et al., 1956T = 14 to 350 K.; DH
146.57298.1Stull, 1937T = 90 to 320 K.; DH

Phase change data

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible 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 as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
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
Tboil358.0 ± 0.3KAVGN/AAverage of 6 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus230.96KN/AGoates, Ott, et al., 1976Uncertainty assigned by TRC = 0.06 K; TRC
Tfus231.25KN/ATimmermans, 1952Uncertainty assigned by TRC = 0.5 K; TRC
Tfus231.3KN/ATimmermans, 1935Uncertainty assigned by TRC = 1. K; TRC
Tfus231.25KN/ATimmermans, 1934Uncertainty assigned by TRC = 0.4 K; TRC
Quantity Value Units Method Reference Comment
Ttriple230.92KN/AScott, McCullough, et al., 1956, 2Uncertainty assigned by TRC = 0.08 K; by extrapolation of 1/f to 0.0; TRC
Ttriple230.94KN/AScott, McCullough, et al., 1956, 2Uncertainty assigned by TRC = 0.05 K; TRC
Ttriple231.1KN/AStull, 1937, 2Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Tc560.1KN/AMajer and Svoboda, 1985 
Tc560.1KN/AAmbrose, Cox, et al., 1960Uncertainty assigned by TRC = 0.2 K; Visual, PRT, IPTS-48; TRC
Tc560.070KN/ADouslin, Moore, et al., 1958Uncertainty assigned by TRC = 0.07 K; TRC
Tc559.7KN/AYoung, 1889Uncertainty assigned by TRC = 0.6 K; by visual observation of meniscus; TRC
Quantity Value Units Method Reference Comment
Pc45.505barN/ADouslin, Moore, et al., 1958Uncertainty assigned by TRC = 0.0506 bar; TRC
Pc45.2123barN/AYoung, 1889Uncertainty assigned by TRC = 0.3999 bar; vapor pressure at critical temperature; TRC
Quantity Value Units Method Reference Comment
Vc0.269l/molN/ADouslin, Moore, et al., 1958Uncertainty assigned by TRC = 0.008 l/mol; TRC
Vc0.462l/molN/AYoung, 1889Uncertainty assigned by TRC = 0.004 l/mol; TRC
Quantity Value Units Method Reference Comment
Δvap34.68kJ/molN/AMajer and Svoboda, 1985 
Δvap34.5kJ/molN/ABoublik, Fried, et al., 1984Based on data from 255. to 360. K. See also Basarová and Svoboda, 1991.; AC
Δvap34.53kJ/molVFindlay, 1969ALS
Δvap34.6kJ/molVScott, McCullough, et al., 1956, 3ALS

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
31.19357.9N/AMajer and Svoboda, 1985 
31.9373.AStephenson and Malanowski, 1987Based on data from 358. to 530. K.; AC
31.8388.AStephenson and Malanowski, 1987Based on data from 373. to 419. K.; AC
31.0429.AStephenson and Malanowski, 1987Based on data from 414. to 501. K.; AC
30.9512.AStephenson and Malanowski, 1987Based on data from 497. to 561. K.; AC
33.6327.EBStephenson and Malanowski, 1987Based on data from 312. to 394. K. See also Scott, McCullough, et al., 1956.; AC
33.5 ± 0.1318.CScott, McCullough, et al., 1956AC
32.4 ± 0.1337.CScott, McCullough, et al., 1956AC
31.2 ± 0.1358.CScott, McCullough, et al., 1956AC
29.7 ± 0.1382.CScott, McCullough, et al., 1956AC

Enthalpy of vaporization

ΔvapH = A exp(-βTr) (1 − Tr)β
    ΔvapH = Enthalpy of vaporization (at saturation pressure) (kJ/mol)
    Tr = reduced temperature (T / Tc)

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Temperature (K) A (kJ/mol) β Tc (K) Reference Comment
318. to 382.49.80.2823560.1Majer and Svoboda, 1985 

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Temperature (K) A B C Reference Comment
255.30 to 357.004.362251409.848-34.792Young, 1889, 2Coefficents calculated by NIST from author's data.

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Reference Comment
11.305230.94Scott, McCullough, et al., 1956DH
11.31230.9Domalski and Hearing, 1996AC
10.397231.10Stull, 1937DH

Entropy of fusion

ΔfusS (J/mol*K) Temperature (K) Reference Comment
48.95230.94Scott, McCullough, et al., 1956DH
44.99231.10Stull, 1937DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


Reaction thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible 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 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

C6H4F- + Hydrogen cation = Benzene, fluoro-

By formula: C6H4F- + H+ = C6H5F

Quantity Value Units Method Reference Comment
Δr1618. ± 8.8kJ/molG+TSBuker, Nibbering, et al., 1997gas phase; B
Δr1620. ± 8.8kJ/molG+TSAndrade and Riveros, 1996gas phase; B
Δr1620. ± 10.kJ/molTDEqMeot-ner and Kafafi, 1988gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B
Δr1620. ± 10.kJ/molBranWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B
Δr1620. ± 23.kJ/molG+TSBriscese and Riveros, 1975gas phase; B
Quantity Value Units Method Reference Comment
Δr1584. ± 8.4kJ/molIMREBuker, Nibbering, et al., 1997gas phase; B
Δr1586. ± 8.4kJ/molIMREAndrade and Riveros, 1996gas phase; B
Δr1585. ± 8.4kJ/molTDEqMeot-ner and Kafafi, 1988gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B
Δr1586. ± 11.kJ/molH-TSWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B
Δr1586. ± 22.kJ/molIMRBBriscese and Riveros, 1975gas phase; B

Bromine anion + Benzene, fluoro- = (Bromine anion • Benzene, fluoro-)

By formula: Br- + C6H5F = (Br- • C6H5F)

Quantity Value Units Method Reference Comment
Δr44.4 ± 6.7kJ/molIMREPaul and Kebarle, 1991gas phase; ΔGaff measured at 303 K, corrected to 423 K, ΔSaff taken as that of PhNO2..Br-; B,M
Quantity Value Units Method Reference Comment
Δr84.J/mol*KN/APaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr8.8 ± 4.2kJ/molIMREPaul and Kebarle, 1991gas phase; ΔGaff measured at 303 K, corrected to 423 K, ΔSaff taken as that of PhNO2..Br-; B

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
8.8423.PHPMSPaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M

C6H5F+ + Benzene, fluoro- = (C6H5F+ • Benzene, fluoro-)

By formula: C6H5F+ + C6H5F = (C6H5F+ • C6H5F)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Δr30.kJ/molPIRuhl, Bisling, et al., 1986gas phase; from vIP of perpendicular dimer; M
Δr59.0kJ/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
22.356.PHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; Entropy change calculated or estimated; M

C6H6+ + Benzene, fluoro- = (C6H6+ • Benzene, fluoro-)

By formula: C6H6+ + C6H5F = (C6H6+ • C6H5F)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Δr28.kJ/molPIRuhl, Bisling, et al., 1986gas phase; from vIP of perpendicular dimer; M
Δr71.1kJ/molPHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; M
Quantity Value Units Method Reference Comment
Δr130.J/mol*KPHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; M

C6H4F- + Hydrogen cation = Benzene, fluoro-

By formula: C6H4F- + H+ = C6H5F

Quantity Value Units Method Reference Comment
Δr1671.9 ± 3.8kJ/molBranWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B
Quantity Value Units Method Reference Comment
Δr1639. ± 4.2kJ/molH-TSWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B

C6H4F- + Hydrogen cation = Benzene, fluoro-

By formula: C6H4F- + H+ = C6H5F

Quantity Value Units Method Reference Comment
Δr1654. ± 8.4kJ/molBranWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B
Quantity Value Units Method Reference Comment
Δr1619. ± 8.8kJ/molH-TSWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B

C6H7N+ + Benzene, fluoro- = (C6H7N+ • Benzene, fluoro-)

By formula: C6H7N+ + C6H5F = (C6H7N+ • C6H5F)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Δr49.0kJ/molPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; M
Quantity Value Units Method Reference Comment
Δr111.J/mol*KPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; M

Nitric oxide anion + Benzene, fluoro- = (Nitric oxide anion • Benzene, fluoro-)

By formula: NO- + C6H5F = (NO- • C6H5F)

Quantity Value Units Method Reference Comment
Δr158.kJ/molICRReents and Freiser, 1981gas phase; switching reaction,Thermochemical ladder(NO+)C2H5OH, Entropy change calculated or estimated; Farid and McMahon, 1978; M

Chlorine anion + Benzene, fluoro- = (Chlorine anion • Benzene, fluoro-)

By formula: Cl- + C6H5F = (Cl- • C6H5F)

Quantity Value Units Method Reference Comment
Δr24.7kJ/molTDEqFrench, Ikuta, et al., 1982gas phase; B

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
25.300.PHPMSFrench, Ikuta, et al., 1982gas phase; M

C7H8+ + Benzene, fluoro- = (C7H8+ • Benzene, fluoro-)

By formula: C7H8+ + C6H5F = (C7H8+ • C6H5F)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Δr16.kJ/molPIRuhl, Bisling, et al., 1986gas phase; from vIP of perpendicular dimer; M

NH4+ + Benzene, fluoro- = (NH4+ • Benzene, fluoro-)

By formula: H4N+ + C6H5F = (H4N+ • C6H5F)

Quantity Value Units Method Reference Comment
Δr60.2kJ/molPHPMSDeakyne and Meot-Ner (Mautner), 1985gas phase; M
Quantity Value Units Method Reference Comment
Δr75.3J/mol*KPHPMSDeakyne and Meot-Ner (Mautner), 1985gas phase; M

(V- • Benzene, fluoro-) + Benzene = (V- • Benzene • Benzene, fluoro-)

By formula: (V- • C6H5F) + C6H6 = (V- • C6H6 • C6H5F)

Quantity Value Units Method Reference Comment
Δr10. ± 63.kJ/molN/AJudai, Hirano, et al., 1997gas phase; B

V- + Benzene, fluoro- = (V- • Benzene, fluoro-)

By formula: V- + C6H5F = (V- • C6H5F)

Quantity Value Units Method Reference Comment
Δr60. ± 16.kJ/molN/AJudai, Hirano, et al., 1997gas phase; B

(Lithium ion (1+) • Benzene, fluoro-) + Benzene, fluoro- = (Lithium ion (1+) • 2Benzene, fluoro-)

By formula: (Li+ • C6H5F) + C6H5F = (Li+ • 2C6H5F)

Quantity Value Units Method Reference Comment
Δr95. ± 3.kJ/molCIDTAmunugama and Rodgers, 2002RCD

(Sodium ion (1+) • Benzene, fluoro-) + Benzene, fluoro- = (Sodium ion (1+) • 2Benzene, fluoro-)

By formula: (Na+ • C6H5F) + C6H5F = (Na+ • 2C6H5F)

Quantity Value Units Method Reference Comment
Δr66. ± 4.kJ/molCIDTAmunugama and Rodgers, 2002RCD

(Cesium ion (1+) • Benzene, fluoro-) + Benzene, fluoro- = (Cesium ion (1+) • 2Benzene, fluoro-)

By formula: (Cs+ • C6H5F) + C6H5F = (Cs+ • 2C6H5F)

Quantity Value Units Method Reference Comment
Δr44.8 ± 4.6kJ/molCIDTAmunugama and Rodgers, 2002RCD

(Rubidium ion (1+) • Benzene, fluoro-) + Benzene, fluoro- = (Rubidium ion (1+) • 2Benzene, fluoro-)

By formula: (Rb+ • C6H5F) + C6H5F = (Rb+ • 2C6H5F)

Quantity Value Units Method Reference Comment
Δr47.3 ± 5.0kJ/molCIDTAmunugama and Rodgers, 2002RCD

(Potassium ion (1+) • Benzene, fluoro-) + Benzene, fluoro- = (Potassium ion (1+) • 2Benzene, fluoro-)

By formula: (K+ • C6H5F) + C6H5F = (K+ • 2C6H5F)

Quantity Value Units Method Reference Comment
Δr50. ± 3.kJ/molCIDTAmunugama and Rodgers, 2002RCD

Lithium ion (1+) + Benzene, fluoro- = (Lithium ion (1+) • Benzene, fluoro-)

By formula: Li+ + C6H5F = (Li+ • C6H5F)

Quantity Value Units Method Reference Comment
Δr147. ± 21.kJ/molCIDTAmunugama and Rodgers, 2002RCD

Sodium ion (1+) + Benzene, fluoro- = (Sodium ion (1+) • Benzene, fluoro-)

By formula: Na+ + C6H5F = (Na+ • C6H5F)

Quantity Value Units Method Reference Comment
Δr70. ± 3.kJ/molCIDTAmunugama and Rodgers, 2002RCD

Cesium ion (1+) + Benzene, fluoro- = (Cesium ion (1+) • Benzene, fluoro-)

By formula: Cs+ + C6H5F = (Cs+ • C6H5F)

Quantity Value Units Method Reference Comment
Δr50.2 ± 5.0kJ/molCIDTAmunugama and Rodgers, 2002RCD

Rubidium ion (1+) + Benzene, fluoro- = (Rubidium ion (1+) • Benzene, fluoro-)

By formula: Rb+ + C6H5F = (Rb+ • C6H5F)

Quantity Value Units Method Reference Comment
Δr53.6 ± 5.4kJ/molCIDTAmunugama and Rodgers, 2002RCD

Potassium ion (1+) + Benzene, fluoro- = (Potassium ion (1+) • Benzene, fluoro-)

By formula: K+ + C6H5F = (K+ • C6H5F)

Quantity Value Units Method Reference Comment
Δr55. ± 3.kJ/molCIDTAmunugama and Rodgers, 2002RCD

Chromium ion (1+) + Benzene, fluoro- = (Chromium ion (1+) • Benzene, fluoro-)

By formula: Cr+ + C6H5F = (Cr+ • C6H5F)

Quantity Value Units Method Reference Comment
Δr164.kJ/molRAKRyzhov, 1999RCD

Henry's Law data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible 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: 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
0.12 QN/ASeveral references are given in the list of Henry's law constants but not assigned to specific species.
0.16 QN/A missing citation give several references for the Henry's law constants but don't assign them to specific species.
0.16 LN/A 
0.164100.MN/A 

Gas phase ion energetics data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
LL - Sharon G. Lias and Joel F. Liebman

View reactions leading to C6H5F+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)9.20 ± 0.01eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)755.9kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity726.6kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
9.20PEFujisawa, Ohno, et al., 1986LBLHLM
9.20PEKimura, Katsumata, et al., 1981LLK
9.22PESell, Mintz, et al., 1978LLK
9.17PEBehan, Johnstone, et al., 1976LLK
9.75EIBaldwin, Loudon, et al., 1976LLK
9.11PEDebies and Rabalais, 1973LLK
9.20SSmith and Raymonda, 1971LLK
9.20SGilbert and Sandorfy, 1971LLK
9.182PIMomigny, Goffart, et al., 1968RDSH
9.21 ± 0.04PEClark and Frost, 1967RDSH
9.20 ± 0.01PIWatanabe, Nakayama, et al., 1962RDSH
9.20PIBralsford, Harris, et al., 1960RDSH
9.200 ± 0.005SHammond, Price, et al., 1950RDSH
9.22PESell and Kupperman, 1978Vertical value; LLK
9.37PEKobayashi, 1978Vertical value; LLK
9.19PEStreets and Ceasar, 1973Vertical value; LLK
9.35 ± 0.03PEKlessinger, 1972Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C2H3F+16.13 ± 0.13C4H2PIPECONishimura, Meisels, et al., 1991LL
C3H2F+15.13 ± 0.13C3H3PIPECONishimura, Meisels, et al., 1991LL
C3H2F+15.8 ± 0.1?EIMomigny, 1959RDSH
C3H3+15.13 ± 0.13C3H2FPIPECONishimura, Meisels, et al., 1991LL
C3H3+14.3 ± 0.1?EIMomigny, 1959RDSH
C4H2+15.13 ± 0.13C2H3FPIPECONishimura, Meisels, et al., 1991LL
C4H3F+13.14 ± 0.05C2H2PIPECONishimura, Meisels, et al., 1991LL
C4H3F+14.73C2H2EIHowe and Williams, 1969RDSH
C4H4+15.90 ± 0.09C2HFPIPECONishimura, Meisels, et al., 1991LL
C4H4+17.0 ± 0.1?EIMomigny, 1959RDSH
C5H2F+16.13 ± 0.13CH3PIPECONishimura, Meisels, et al., 1991LL
C5H3+15.13 ± 0.13CH2FPIPECONishimura, Meisels, et al., 1991LL
C6H4+15.4 ± 0.1HFEIMomigny, 1959RDSH
C6H4F+14.1HEIYeo and Williams, 1970RDSH
C6H5+13.10 ± 0.05FPIPECONishimura, Meisels, et al., 1991LL
C6H5+14.5 ± 0.1FEIMajer and Patrick, 1962RDSH

De-protonation reactions

C6H4F- + Hydrogen cation = Benzene, fluoro-

By formula: C6H4F- + H+ = C6H5F

Quantity Value Units Method Reference Comment
Δr1618. ± 8.8kJ/molG+TSBuker, Nibbering, et al., 1997gas phase; B
Δr1620. ± 8.8kJ/molG+TSAndrade and Riveros, 1996gas phase; B
Δr1620. ± 10.kJ/molTDEqMeot-ner and Kafafi, 1988gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B
Δr1620. ± 10.kJ/molBranWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B
Δr1620. ± 23.kJ/molG+TSBriscese and Riveros, 1975gas phase; B
Quantity Value Units Method Reference Comment
Δr1584. ± 8.4kJ/molIMREBuker, Nibbering, et al., 1997gas phase; B
Δr1586. ± 8.4kJ/molIMREAndrade and Riveros, 1996gas phase; B
Δr1585. ± 8.4kJ/molTDEqMeot-ner and Kafafi, 1988gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B
Δr1586. ± 11.kJ/molH-TSWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B
Δr1586. ± 22.kJ/molIMRBBriscese and Riveros, 1975gas phase; B

C6H4F- + Hydrogen cation = Benzene, fluoro-

By formula: C6H4F- + H+ = C6H5F

Quantity Value Units Method Reference Comment
Δr1671.9 ± 3.8kJ/molBranWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B
Quantity Value Units Method Reference Comment
Δr1639. ± 4.2kJ/molH-TSWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B

C6H4F- + Hydrogen cation = Benzene, fluoro-

By formula: C6H4F- + H+ = C6H5F

Quantity Value Units Method Reference Comment
Δr1654. ± 8.4kJ/molBranWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B
Quantity Value Units Method Reference Comment
Δr1619. ± 8.8kJ/molH-TSWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B

Ion clustering data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible 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 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. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

Bromine anion + Benzene, fluoro- = (Bromine anion • Benzene, fluoro-)

By formula: Br- + C6H5F = (Br- • C6H5F)

Quantity Value Units Method Reference Comment
Δr44.4 ± 6.7kJ/molIMREPaul and Kebarle, 1991gas phase; ΔGaff measured at 303 K, corrected to 423 K, ΔSaff taken as that of PhNO2..Br-; B,M
Quantity Value Units Method Reference Comment
Δr84.J/mol*KN/APaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr8.8 ± 4.2kJ/molIMREPaul and Kebarle, 1991gas phase; ΔGaff measured at 303 K, corrected to 423 K, ΔSaff taken as that of PhNO2..Br-; B

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
8.8423.PHPMSPaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M

C6H5F+ + Benzene, fluoro- = (C6H5F+ • Benzene, fluoro-)

By formula: C6H5F+ + C6H5F = (C6H5F+ • C6H5F)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Δr30.kJ/molPIRuhl, Bisling, et al., 1986gas phase; from vIP of perpendicular dimer; M
Δr59.0kJ/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
22.356.PHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; Entropy change calculated or estimated; M

C6H6+ + Benzene, fluoro- = (C6H6+ • Benzene, fluoro-)

By formula: C6H6+ + C6H5F = (C6H6+ • C6H5F)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Δr28.kJ/molPIRuhl, Bisling, et al., 1986gas phase; from vIP of perpendicular dimer; M
Δr71.1kJ/molPHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; M
Quantity Value Units Method Reference Comment
Δr130.J/mol*KPHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; M

C6H7N+ + Benzene, fluoro- = (C6H7N+ • Benzene, fluoro-)

By formula: C6H7N+ + C6H5F = (C6H7N+ • C6H5F)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Δr49.0kJ/molPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; M
Quantity Value Units Method Reference Comment
Δr111.J/mol*KPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; M

C7H8+ + Benzene, fluoro- = (C7H8+ • Benzene, fluoro-)

By formula: C7H8+ + C6H5F = (C7H8+ • C6H5F)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Δr16.kJ/molPIRuhl, Bisling, et al., 1986gas phase; from vIP of perpendicular dimer; M

Chlorine anion + Benzene, fluoro- = (Chlorine anion • Benzene, fluoro-)

By formula: Cl- + C6H5F = (Cl- • C6H5F)

Quantity Value Units Method Reference Comment
Δr24.7kJ/molTDEqFrench, Ikuta, et al., 1982gas phase; B

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
25.300.PHPMSFrench, Ikuta, et al., 1982gas phase; M

Chromium ion (1+) + Benzene, fluoro- = (Chromium ion (1+) • Benzene, fluoro-)

By formula: Cr+ + C6H5F = (Cr+ • C6H5F)

Quantity Value Units Method Reference Comment
Δr164.kJ/molRAKRyzhov, 1999RCD

Cesium ion (1+) + Benzene, fluoro- = (Cesium ion (1+) • Benzene, fluoro-)

By formula: Cs+ + C6H5F = (Cs+ • C6H5F)

Quantity Value Units Method Reference Comment
Δr50.2 ± 5.0kJ/molCIDTAmunugama and Rodgers, 2002RCD

(Cesium ion (1+) • Benzene, fluoro-) + Benzene, fluoro- = (Cesium ion (1+) • 2Benzene, fluoro-)

By formula: (Cs+ • C6H5F) + C6H5F = (Cs+ • 2C6H5F)

Quantity Value Units Method Reference Comment
Δr44.8 ± 4.6kJ/molCIDTAmunugama and Rodgers, 2002RCD

NH4+ + Benzene, fluoro- = (NH4+ • Benzene, fluoro-)

By formula: H4N+ + C6H5F = (H4N+ • C6H5F)

Quantity Value Units Method Reference Comment
Δr60.2kJ/molPHPMSDeakyne and Meot-Ner (Mautner), 1985gas phase; M
Quantity Value Units Method Reference Comment
Δr75.3J/mol*KPHPMSDeakyne and Meot-Ner (Mautner), 1985gas phase; M

Potassium ion (1+) + Benzene, fluoro- = (Potassium ion (1+) • Benzene, fluoro-)

By formula: K+ + C6H5F = (K+ • C6H5F)

Quantity Value Units Method Reference Comment
Δr55. ± 3.kJ/molCIDTAmunugama and Rodgers, 2002RCD

(Potassium ion (1+) • Benzene, fluoro-) + Benzene, fluoro- = (Potassium ion (1+) • 2Benzene, fluoro-)

By formula: (K+ • C6H5F) + C6H5F = (K+ • 2C6H5F)

Quantity Value Units Method Reference Comment
Δr50. ± 3.kJ/molCIDTAmunugama and Rodgers, 2002RCD

Lithium ion (1+) + Benzene, fluoro- = (Lithium ion (1+) • Benzene, fluoro-)

By formula: Li+ + C6H5F = (Li+ • C6H5F)

Quantity Value Units Method Reference Comment
Δr147. ± 21.kJ/molCIDTAmunugama and Rodgers, 2002RCD

(Lithium ion (1+) • Benzene, fluoro-) + Benzene, fluoro- = (Lithium ion (1+) • 2Benzene, fluoro-)

By formula: (Li+ • C6H5F) + C6H5F = (Li+ • 2C6H5F)

Quantity Value Units Method Reference Comment
Δr95. ± 3.kJ/molCIDTAmunugama and Rodgers, 2002RCD

Nitric oxide anion + Benzene, fluoro- = (Nitric oxide anion • Benzene, fluoro-)

By formula: NO- + C6H5F = (NO- • C6H5F)

Quantity Value Units Method Reference Comment
Δr158.kJ/molICRReents and Freiser, 1981gas phase; switching reaction,Thermochemical ladder(NO+)C2H5OH, Entropy change calculated or estimated; Farid and McMahon, 1978; M

Sodium ion (1+) + Benzene, fluoro- = (Sodium ion (1+) • Benzene, fluoro-)

By formula: Na+ + C6H5F = (Na+ • C6H5F)

Quantity Value Units Method Reference Comment
Δr70. ± 3.kJ/molCIDTAmunugama and Rodgers, 2002RCD

(Sodium ion (1+) • Benzene, fluoro-) + Benzene, fluoro- = (Sodium ion (1+) • 2Benzene, fluoro-)

By formula: (Na+ • C6H5F) + C6H5F = (Na+ • 2C6H5F)

Quantity Value Units Method Reference Comment
Δr66. ± 4.kJ/molCIDTAmunugama and Rodgers, 2002RCD

Rubidium ion (1+) + Benzene, fluoro- = (Rubidium ion (1+) • Benzene, fluoro-)

By formula: Rb+ + C6H5F = (Rb+ • C6H5F)

Quantity Value Units Method Reference Comment
Δr53.6 ± 5.4kJ/molCIDTAmunugama and Rodgers, 2002RCD

(Rubidium ion (1+) • Benzene, fluoro-) + Benzene, fluoro- = (Rubidium ion (1+) • 2Benzene, fluoro-)

By formula: (Rb+ • C6H5F) + C6H5F = (Rb+ • 2C6H5F)

Quantity Value Units Method Reference Comment
Δr47.3 ± 5.0kJ/molCIDTAmunugama and Rodgers, 2002RCD

V- + Benzene, fluoro- = (V- • Benzene, fluoro-)

By formula: V- + C6H5F = (V- • C6H5F)

Quantity Value Units Method Reference Comment
Δr60. ± 16.kJ/molN/AJudai, Hirano, et al., 1997gas phase; B

IR Spectrum

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), UV/Visible spectrum, References, Notes

Data compiled by: Coblentz Society, Inc.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director


Mass spectrum (electron ionization)

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, UV/Visible 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

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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- 529
NIST MS number 229256

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


UV/Visible spectrum

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law 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 by: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis spectrum
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Additional Data

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Source Bowden and Braude, 1952
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 11510
Instrument Hilger, Beckman spectrophotometer
Melting point - 42.2
Boiling point 84.7

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Good, Scott, et al., 1956
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Scott, D.W.; McCullough, J.P.; Good, W.D.; Messerly, J.F.; Pennington, R.E.; Kincheloe, T.C.; Hossenlopp, I.A.; Douslin, D.R.; Waddington, G., Fluorobenzene: Thermodynamic properties in the solid, liquid and vapor states, a revised vibrational assignment, J. Am. Chem. Soc., 1956, 78, 5457-5463. [all data]

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Scott, D.W.; McCullough, J.P.; Good, W.D.; Messerly, J.F.; Pennington, R.E.; Kincheloe, T.C.; Hossenlopp, I.A.; Douslin, D.R.; Waddington, G., Fluorobenzene: Thermodynamic Properties in the Solid, Liquid and Vapor States; A Revised Vibrational Assignment, J. Am. Chem. Soc., 1956, 78, 5457-63. [all data]

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Young, S., On the Vapour-Pressures and Specific Volumes of Similar Compounds of Elements in Relation to the Position of those Elements in the Periodic Table, J. Chem. Soc., 1889, 55, 486-521, https://doi.org/10.1039/ct8895500486 . [all data]

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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]

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Kiefer, J.H.; Zhang, Q.; Kern, R.D.; Yao, J.; Jursic, B., Pyrolysis of Aromatic Azines: Pyrazine, Pyrimidine, and Pyridine, J. Phys. Chem. A, 1997, 101, 38, 7061, https://doi.org/10.1021/jp970211z . [all data]

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Kobayashi, 1978
Kobayashi, T., A simple general tendency in photoelectron angular distributions of some monosubstituted benzenes, Phys. Lett., 1978, 69, 105. [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]

Nishimura, Meisels, et al., 1991
Nishimura, T.; Meisels, G.; Niwa, Y., Fragmentation of energy-selected fluorobenzene ion, Bull. Chem. Soc. Jpn., 1991, 64, 2894. [all data]

Momigny, 1959
Momigny, J., Determination et discussion des potentials d'apparition d'ions fragmentaires dans le benzene et ses derives monohalogenes, Bull. Soc. Roy. Sci. Liege, 1959, 28, 251. [all data]

Howe and Williams, 1969
Howe, I.; Williams, D.H., Calculation and qualitative predictions of mass spectra. Mono- and paradisubstituted benzenes, J. Am. Chem. Soc., 1969, 91, 7137. [all data]

Yeo and Williams, 1970
Yeo, A.N.H.; Williams, D.H., Rearrangement in the molecular ions of halogenotoluenes prior to fragmentation in the mass spectrometer, Chem. Commun., 1970, 886. [all data]

Majer and Patrick, 1962
Majer, J.R.; Patrick, C.R., Electron impact on some halogenated aromatic compounds, J. Chem. Soc. Faraday Trans., 1962, 58, 17. [all data]

Bowden and Braude, 1952
Bowden, K.; Braude, E.A., J. Chem. Soc., 1952, 1068. [all data]


Notes

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