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Benzene, fluoro-

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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-150.8 ± 1.4kJ/molCcrGood, Scott, et al., 1956Corrected for CODATA value of «DELTA»fH; ALS
Quantity Value Units Method Reference Comment
Deltacliquid-3103.9 ± 1.2kJ/molCcrGood, Scott, et al., 1956Corrected for CODATA value of «DELTA»fH; ALS
Deltacliquid-3126.kJ/molCcbSwarts, 1919Not corrected for CODATA value of «DELTA»fH; 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

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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:
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
Deltavap34.68kJ/molN/AMajer and Svoboda, 1985 
Deltavap34.5kJ/molN/ABoublik, Fried, et al., 1984Based on data from 255. - 360. K. See also Basarová and Svoboda, 1991.; AC
Deltavap34.53kJ/molVFindlay, 1969ALS
Deltavap34.6kJ/molVScott, McCullough, et al., 1956, 3ALS

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
31.19357.9N/AMajer and Svoboda, 1985 
31.9373.AStephenson and Malanowski, 1987Based on data from 358. - 530. K.; AC
31.8388.AStephenson and Malanowski, 1987Based on data from 373. - 419. K.; AC
31.0429.AStephenson and Malanowski, 1987Based on data from 414. - 501. K.; AC
30.9512.AStephenson and Malanowski, 1987Based on data from 497. - 561. K.; AC
33.6327.EBStephenson and Malanowski, 1987Based on data from 312. - 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) beta Tc (K) Reference Comment
318. - 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 - 357.004.362251409.848-34.792Young, 1889, 2Coefficents calculated by NIST from author's data.

Enthalpy of fusion

DeltafusH (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

DeltafusS (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, Gas Chromatography, NIST Free Links, 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
Deltar1618. ± 8.8kJ/molG+TSBuker, Nibbering, et al., 1997gas phase; B
Deltar1620. ± 8.8kJ/molG+TSAndrade and Riveros, 1996gas phase; B
Deltar1620. ± 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
Deltar1620. ± 10.kJ/molBranWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B
Deltar1620. ± 23.kJ/molG+TSBriscese and Riveros, 1975gas phase; B
Quantity Value Units Method Reference Comment
Deltar1584. ± 8.4kJ/molIMREBuker, Nibbering, et al., 1997gas phase; B
Deltar1586. ± 8.4kJ/molIMREAndrade and Riveros, 1996gas phase; B
Deltar1585. ± 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
Deltar1586. ± 11.kJ/molH-TSWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B
Deltar1586. ± 22.kJ/molIMRBBriscese and Riveros, 1975gas phase; B

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

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

Quantity Value Units Method Reference Comment
Deltar44.4 ± 6.7kJ/molIMREPaul and Kebarle, 1991gas phase; «DELTA»Gaff measured at 303 K, corrected to 423 K, «DELTA»Saff taken as that of PhNO2..Br-; B,M
Quantity Value Units Method Reference Comment
Deltar84.J/mol*KN/APaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar8.8 ± 4.2kJ/molIMREPaul and Kebarle, 1991gas phase; «DELTA»Gaff measured at 303 K, corrected to 423 K, «DELTA»Saff taken as that of PhNO2..Br-; B

Free energy of reaction

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

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

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

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar30.kJ/molPIRuhl, Bisling, et al., 1986gas phase; from vIP of perpendicular dimer; M
Deltar59.0kJ/molPHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar110.J/mol*KN/AMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; Entropy change calculated or estimated; M

Free energy of reaction

DeltarG° (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+ bullet Benzene, fluoro-)

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

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar28.kJ/molPIRuhl, Bisling, et al., 1986gas phase; from vIP of perpendicular dimer; M
Deltar71.1kJ/molPHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; M
Quantity Value Units Method Reference Comment
Deltar130.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
Deltar1671.9 ± 3.8kJ/molBranWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B
Quantity Value Units Method Reference Comment
Deltar1639. ± 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
Deltar1654. ± 8.4kJ/molBranWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B
Quantity Value Units Method Reference Comment
Deltar1619. ± 8.8kJ/molH-TSWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B

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

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

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar49.0kJ/molPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; M
Quantity Value Units Method Reference Comment
Deltar111.J/mol*KPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; M

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

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

Quantity Value Units Method Reference Comment
Deltar158.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 bullet Benzene, fluoro-)

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

Quantity Value Units Method Reference Comment
Deltar24.7kJ/molTDEqFrench, Ikuta, et al., 1982gas phase; B

Free energy of reaction

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

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

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

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar16.kJ/molPIRuhl, Bisling, et al., 1986gas phase; from vIP of perpendicular dimer; M

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

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

Quantity Value Units Method Reference Comment
Deltar60.2kJ/molPHPMSDeakyne and Meot-Ner (Mautner), 1985gas phase; M
Quantity Value Units Method Reference Comment
Deltar75.3J/mol*KPHPMSDeakyne and Meot-Ner (Mautner), 1985gas phase; M

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

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

Quantity Value Units Method Reference Comment
Deltar10. ± 63.kJ/molN/AJudai, Hirano, et al., 1997gas phase; B

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

By formula: V- + C6H5F = (V- bullet C6H5F)

Quantity Value Units Method Reference Comment
Deltar60. ± 16.kJ/molN/AJudai, Hirano, et al., 1997gas phase; B

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

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

Quantity Value Units Method Reference Comment
Deltar95. ± 3.kJ/molCIDTAmunugama and Rodgers, 2002RCD

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

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

Quantity Value Units Method Reference Comment
Deltar66. ± 4.kJ/molCIDTAmunugama and Rodgers, 2002RCD

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

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

Quantity Value Units Method Reference Comment
Deltar44.8 ± 4.6kJ/molCIDTAmunugama and Rodgers, 2002RCD

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

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

Quantity Value Units Method Reference Comment
Deltar47.3 ± 5.0kJ/molCIDTAmunugama and Rodgers, 2002RCD

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

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

Quantity Value Units Method Reference Comment
Deltar50. ± 3.kJ/molCIDTAmunugama and Rodgers, 2002RCD

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

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

Quantity Value Units Method Reference Comment
Deltar147. ± 21.kJ/molCIDTAmunugama and Rodgers, 2002RCD

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

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

Quantity Value Units Method Reference Comment
Deltar70. ± 3.kJ/molCIDTAmunugama and Rodgers, 2002RCD

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

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

Quantity Value Units Method Reference Comment
Deltar50.2 ± 5.0kJ/molCIDTAmunugama and Rodgers, 2002RCD

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

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

Quantity Value Units Method Reference Comment
Deltar53.6 ± 5.4kJ/molCIDTAmunugama and Rodgers, 2002RCD

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

By formula: K+ + C6H5F = (K+ bullet C6H5F)

Quantity Value Units Method Reference Comment
Deltar55. ± 3.kJ/molCIDTAmunugama and Rodgers, 2002RCD

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

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

Quantity Value Units Method Reference Comment
Deltar164.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, Gas Chromatography, NIST Free Links, 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, Gas Chromatography, NIST Free Links, 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
Deltar1618. ± 8.8kJ/molG+TSBuker, Nibbering, et al., 1997gas phase; B
Deltar1620. ± 8.8kJ/molG+TSAndrade and Riveros, 1996gas phase; B
Deltar1620. ± 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
Deltar1620. ± 10.kJ/molBranWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B
Deltar1620. ± 23.kJ/molG+TSBriscese and Riveros, 1975gas phase; B
Quantity Value Units Method Reference Comment
Deltar1584. ± 8.4kJ/molIMREBuker, Nibbering, et al., 1997gas phase; B
Deltar1586. ± 8.4kJ/molIMREAndrade and Riveros, 1996gas phase; B
Deltar1585. ± 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
Deltar1586. ± 11.kJ/molH-TSWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B
Deltar1586. ± 22.kJ/molIMRBBriscese and Riveros, 1975gas phase; B

C6H4F- + Hydrogen cation = Benzene, fluoro-

By formula: C6H4F- + H+ = C6H5F

Quantity Value Units Method Reference Comment
Deltar1671.9 ± 3.8kJ/molBranWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B
Quantity Value Units Method Reference Comment
Deltar1639. ± 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
Deltar1654. ± 8.4kJ/molBranWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B
Quantity Value Units Method Reference Comment
Deltar1619. ± 8.8kJ/molH-TSWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B

Ion clustering 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. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

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

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

Quantity Value Units Method Reference Comment
Deltar44.4 ± 6.7kJ/molIMREPaul and Kebarle, 1991gas phase; «DELTA»Gaff measured at 303 K, corrected to 423 K, «DELTA»Saff taken as that of PhNO2..Br-; B,M
Quantity Value Units Method Reference Comment
Deltar84.J/mol*KN/APaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar8.8 ± 4.2kJ/molIMREPaul and Kebarle, 1991gas phase; «DELTA»Gaff measured at 303 K, corrected to 423 K, «DELTA»Saff taken as that of PhNO2..Br-; B

Free energy of reaction

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

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

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

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar30.kJ/molPIRuhl, Bisling, et al., 1986gas phase; from vIP of perpendicular dimer; M
Deltar59.0kJ/molPHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar110.J/mol*KN/AMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; Entropy change calculated or estimated; M

Free energy of reaction

DeltarG° (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+ bullet Benzene, fluoro-)

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

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar28.kJ/molPIRuhl, Bisling, et al., 1986gas phase; from vIP of perpendicular dimer; M
Deltar71.1kJ/molPHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; M
Quantity Value Units Method Reference Comment
Deltar130.J/mol*KPHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; M

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

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

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar49.0kJ/molPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; M
Quantity Value Units Method Reference Comment
Deltar111.J/mol*KPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; M

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

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

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar16.kJ/molPIRuhl, Bisling, et al., 1986gas phase; from vIP of perpendicular dimer; M

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

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

Quantity Value Units Method Reference Comment
Deltar24.7kJ/molTDEqFrench, Ikuta, et al., 1982gas phase; B

Free energy of reaction

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

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

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

Quantity Value Units Method Reference Comment
Deltar164.kJ/molRAKRyzhov, 1999RCD

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

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

Quantity Value Units Method Reference Comment
Deltar50.2 ± 5.0kJ/molCIDTAmunugama and Rodgers, 2002RCD

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

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

Quantity Value Units Method Reference Comment
Deltar44.8 ± 4.6kJ/molCIDTAmunugama and Rodgers, 2002RCD

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

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

Quantity Value Units Method Reference Comment
Deltar60.2kJ/molPHPMSDeakyne and Meot-Ner (Mautner), 1985gas phase; M
Quantity Value Units Method Reference Comment
Deltar75.3J/mol*KPHPMSDeakyne and Meot-Ner (Mautner), 1985gas phase; M

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

By formula: K+ + C6H5F = (K+ bullet C6H5F)

Quantity Value Units Method Reference Comment
Deltar55. ± 3.kJ/molCIDTAmunugama and Rodgers, 2002RCD

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

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

Quantity Value Units Method Reference Comment
Deltar50. ± 3.kJ/molCIDTAmunugama and Rodgers, 2002RCD

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

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

Quantity Value Units Method Reference Comment
Deltar147. ± 21.kJ/molCIDTAmunugama and Rodgers, 2002RCD

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

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

Quantity Value Units Method Reference Comment
Deltar95. ± 3.kJ/molCIDTAmunugama and Rodgers, 2002RCD

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

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

Quantity Value Units Method Reference Comment
Deltar158.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+) bullet Benzene, fluoro-)

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

Quantity Value Units Method Reference Comment
Deltar70. ± 3.kJ/molCIDTAmunugama and Rodgers, 2002RCD

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

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

Quantity Value Units Method Reference Comment
Deltar66. ± 4.kJ/molCIDTAmunugama and Rodgers, 2002RCD

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

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

Quantity Value Units Method Reference Comment
Deltar53.6 ± 5.4kJ/molCIDTAmunugama and Rodgers, 2002RCD

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

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

Quantity Value Units Method Reference Comment
Deltar47.3 ± 5.0kJ/molCIDTAmunugama and Rodgers, 2002RCD

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

By formula: V- + C6H5F = (V- bullet C6H5F)

Quantity Value Units Method Reference Comment
Deltar60. ± 16.kJ/molN/AJudai, Hirano, et al., 1997gas phase; B

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

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


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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Mass 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

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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: 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

Gas Chromatography

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, NIST Free Links, 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

Kovats' RI, non-polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
PackedC78, Branched paraffin130.664.9Dallos, Sisak, et al., 2000He; Column length: 3.3 m
PackedOV-101100.671.5Righezza, Hassani, et al., 1996N2, Chromosorb G HP; Column length: 5. m
PackedOV-101110.672.6Righezza, Hassani, et al., 1996N2, Chromosorb G HP; Column length: 5. m
PackedOV-10180.663.2Righezza, Hassani, et al., 1996N2, Chromosorb G HP; Column length: 5. m
PackedOV-10190.668.Righezza, Hassani, et al., 1996N2, Chromosorb G HP; Column length: 5. m
PackedOV-101120.673.9Hassani and Meklati, 1992N2, Chromosorb G HP; Column length: 5. m
PackedC78, Branched paraffin130.664.6Reddy, Dutoit, et al., 1992Chromosorb G HP; Column length: 3.3 m
PackedApolane130.666.Dutoit, 1991Column length: 3.7 m
PackedApolane150.680.Evans and Haken, 1987He, Chromosorb G AW DCMS; Column length: 3.7 m
PackedApolane150.680.Haken and Vernon, 1986Chromosorb G AW DCMS; Column length: 3.7 m
PackedSE-30180.671.Oszczapowicz, Osek, et al., 1984N2, Chromosorb W AW; Column length: 3. m
PackedApolane70.651.3Riedo, Fritz, et al., 1976He, Chromosorb; Column length: 2.4 m
PackedSqualane100.643.Vernon and Edwards, 1975N2, DCMS-treated Celite; Column length: 1. m
PackedApiezon L130.681.Wehrli and Kováts, 1959Celite; Column length: 2.25 m

Kovats' RI, non-polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
PackedApiezon M664.1Jalali-Heravi and Garkani-Nejad, 1993Chromosorb W; Column length: 2. m; Program: not specified

Kovats' RI, polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
PackedCarbowax 20M150.996.Haken and Vernon, 1986Chromosorb G AW DCMS; Column length: 3.7 m; Column diameter: 6.4 mm

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

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Column type Active phase I Reference Comment
CapillarySPB-5674.Engel and Ratel, 200760. m/0.32 mm/1. «mu»m, 40. C @ 2. min, 3. K/min, 230. C @ 10. min
CapillarySPB-5674.Deport, Ratel, et al., 200660. m/0.32 mm/1. «mu»m, He, 40. C @ 5. min, 3. K/min, 230. C @ 5. min
CapillaryPetrocol DH659.4Censullo, Jones, et al., 200350. m/0.25 mm/0.5 «mu»m, He, 35. C @ 10. min, 3. K/min, 200. C @ 10. min
CapillaryOV-1654.4Gautzsch and Zinn, 19968. K/min; Tstart: 35. C; Tend: 300. C
PackedSE-30664.Peng, Ding, et al., 1988He, Supelcoport and Chromosorb, 40. C @ 4. min, 10. K/min, 250. C @ 60. min; Column length: 3.05 m
PackedSE-30664.Buchman, Cao, et al., 1984He, Chromosorb AW, 40. C @ 10. min, 10. K/min, 210. C @ 30. min; Column length: 3.05 m

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

View large format table.

Column type Active phase I Reference Comment
PackedCarbowax 20M992.Buchman, Cao, et al., 1984He, Supelcoport, 40. C @ 10. min, 10. K/min, 210. C @ 30. min; Column length: 3.05 m

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryOV-101663.Zenkevich, 200525. m/0.20 mm/0.10 «mu»m, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C

Normal alkane RI, non-polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryOV-101674.Ebrahimi and Hadjmohammadi, 2006Program: not specified
CapillaryMethyl Silicone681.N/AProgram: not specified
CapillaryDB-5684.Sorimachi, Tanabe, et al., 1995He; Column length: 30. m; Program: not specified

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, Gas Chromatography, NIST Free Links, 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
Good, W.D.; Scott, D.W.; Waddington, G., Combustion calorimetry of organic fluorine compounds by a rotating-bomb method, J. Phys. Chem., 1956, 60, 1080-1089. [all data]

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

Scott, McCullough, et al., 1956
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]

Stull, 1937
Stull, D.R., A semi-micro calorimeter for measuring heat capacities at low temperatures, J. Am. Chem. Soc., 1937, 59, 2726-2733. [all data]

Roux, Grolier, et al., 1984
Roux, A.H.; Grolier, J.-P.E.; Inglese, A.; Wilhelm, E., Excess molar enthalpies, excess molar heat capacities and excess molar volumes of (fluorobenzene + an n-alkane), Ber. Bunsenges. Phys. Chem., 1984, 88, 986-992. [all data]

Goates, Ott, et al., 1976
Goates, J.R.; Ott, J.B.; Moellmer, J.F., Solid + Liquid Phase Equilibria and Solid-compound Formation in Halobenzenes + Aromatic Hydrocarbons, J. Chem. Thermodyn., 1976, 8, 217. [all data]

Timmermans, 1952
Timmermans, J., Freezing points of organic compounds. VVI New determinations., Bull. Soc. Chim. Belg., 1952, 61, 393. [all data]

Timmermans, 1935
Timmermans, J., Researches in Stoichiometry. I. The Heat of Fusion of Organic Compounds., Bull. Soc. Chim. Belg., 1935, 44, 17-40. [all data]

Timmermans, 1934
Timmermans, J., Theory of Concentrated Solutions XII., Bull. Soc. Chim. Belg., 1934, 43, 626. [all data]

Scott, McCullough, et al., 1956, 2
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]

Stull, 1937, 2
Stull, D.R., A Semi-micro Calorimeter for Measuring Heat Capacities at Low Temp., J. Am. Chem. Soc., 1937, 59, 2726. [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Ambrose, Cox, et al., 1960
Ambrose, D.; Cox, J.D.; Townsend, R., The critical temperatures of forty organic compounds, Trans. Faraday Soc., 1960, 56, 1452. [all data]

Douslin, Moore, et al., 1958
Douslin, D.R.; Moore, R.T.; Dawson, J.P.; Waddington, G., Pressure-Volume-Temperature Properties of Fluorobenzene, J. Am. Chem. Soc., 1958, 80, 2031. [all data]

Young, 1889
Young, S., On the Vapor Pressures and SPecific Volumes of Similar Compounds of Elements in Relation to the Position of Those Elements in the Periodic Table, J. Chem. Soc., Trans., 1889, 55, 486. [all data]

Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E., The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]

Basarová and Svoboda, 1991
Basarová, Pavlína; Svoboda, Václav, Calculation of heats of vaporization of halogenated hydrocarbons from saturated vapour pressure data, Fluid Phase Equilibria, 1991, 68, 13-34, https://doi.org/10.1016/0378-3812(91)85008-I . [all data]

Findlay, 1969
Findlay, T.J.V., Vapor pressures of fluorobenzenes from 5° to 50°C, J. Chem. Eng. Data, 1969, 14, 229. [all data]

Scott, McCullough, et al., 1956, 3
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, 5457-54. [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Young, 1889, 2
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]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [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]

Andrade and Riveros, 1996
Andrade, P.B.M.; Riveros, J.M., Relative Gas-phase Acidities of Fluoro- and Chlorobenzene, J. Mass Spectrom., 1996, 31, 7, 767, https://doi.org/10.1002/(SICI)1096-9888(199607)31:7<767::AID-JMS345>3.0.CO;2-Q . [all data]

Meot-ner and Kafafi, 1988
Meot-ner, M.; Kafafi, S.A., Carbon Acidities of Aromatic Compounds, J. Am. Chem. Soc., 1988, 110, 19, 6297, https://doi.org/10.1021/ja00227a003 . [all data]

Kiefer, Zhang, et al., 1997
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]

Wenthold and Squires, 1995
Wenthold, P.G.; Squires, R.R., Determination of the gas-phase acidities of halogen-substituted aromatic compounds using the silane-cleavage method, J. Mass Spectrom., 1995, 30, 1, 17, https://doi.org/10.1002/jms.1190300105 . [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]

Paul and Kebarle, 1991
Paul, G.J.C.; Kebarle, P., Stabilities of Complexes of Br- with Substituted Benzenes (SB) Based on Determinations of the Gas-Phase Equilibria Br- + SB = (BrSB)-, J. Am. Chem. Soc., 1991, 113, 4, 1148, https://doi.org/10.1021/ja00004a014 . [all data]

Ruhl, Bisling, et al., 1986
Ruhl, E.; Bisling, P.G.F.; Brutschy, B.; Baumgartel, H., Photoionization of Aromatic van der Waals Complexes in a Supersonic Jet, Chem. Phys. Lett., 1986, 126, 3-4, 232, https://doi.org/10.1016/S0009-2614(86)80075-6 . [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]

Meot-Ner (Mautner) and El-Shall, 1986
Meot-Ner (Mautner), M.; El-Shall, M.S., Ionic Charge Transfer Complexes. 1. Cationic Complexes with Delocalized and Partially Localized pi Systems, J. Am. Chem. Soc., 1986, 108, 15, 4386, https://doi.org/10.1021/ja00275a026 . [all data]

Reents and Freiser, 1981
Reents, W.D.; Freiser, B.S., Gas-Phase Binding Energies and Spectroscopic Properties of NO+ Charge-Transfer Complexes, J. Am. Chem. Soc., 1981, 103, 2791. [all data]

Farid and McMahon, 1978
Farid, R.; McMahon, T.B., Gas-Phase Ion-Molecule Reactions of Alkyl Nitrites by Ion Cyclotron Resonance Spectroscopy, Int. J. Mass Spectrom. Ion Phys., 1978, 27, 2, 163, https://doi.org/10.1016/0020-7381(78)80037-0 . [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]

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]

Judai, Hirano, et al., 1997
Judai, K.; Hirano, M.; Kawamata, H.; Yabushita, S.; Nakajima, A.; Kaya, K., Formation of Vanadium-Arene Complex Anions and Their Photoelectron Spectroscopy, Chem. Phys. Lett., 1997, 270, 1-2, 23, https://doi.org/10.1016/S0009-2614(97)00336-9 . [all data]

Amunugama and Rodgers, 2002
Amunugama, R.; Rodgers, M.T., Influence of substituents on cation-pi interactions. 2. Absolute binding energies of alkali metal cation-fluorobenzene complexes determined by threshold collision-induced dissociation and theoretical studies, J. Phys. Chem. A, 2002, 106, 39, 9092, https://doi.org/10.1021/jp020459a . [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]

Fujisawa, Ohno, et al., 1986
Fujisawa, S.; Ohno, K.; Masuda, S.; Harada, Y., Penning ionization electron spectroscopy of monohalogenobenzenes: C6H5F, C6H5Cl, C6H5Br, and C6H5I, J. Am. Chem. Soc., 1986, 108, 6505. [all data]

Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S., Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]

Sell, Mintz, et al., 1978
Sell, J.A.; Mintz, D.M.; Kupperman, A., Photoelectron angular distributions of carbon-carbon «pi» electrons in ethylene, benzene, and their fluorinated derivatives, Chem. Phys. Lett., 1978, 58, 601. [all data]

Behan, Johnstone, et al., 1976
Behan, J.M.; Johnstone, R.A.W.; Bentley, T.W., An evaluation of empirical methods for calculating the ionization potentials of substituted benzenes, Org. Mass Spectrom., 1976, 11, 207. [all data]

Baldwin, Loudon, et al., 1976
Baldwin, M.A.; Loudon, A.G.; Maccoll, A.; Webb, K.S., The nature and fragmentation pathways of the molecular ions of some arylureas, arylthioureas, acetanilides, thioacetanilides and related compounds, Org. Mass Spectrom., 1976, 11, 1181. [all data]

Debies and Rabalais, 1973
Debies, T.P.; Rabalais, J.W., Photoelectron spectra of substituted benzenes. II. Seven valence electron substituents, J. Electron Spectrosc. Relat. Phenom., 1973, 1, 355. [all data]

Smith and Raymonda, 1971
Smith, D.R.; Raymonda, J.W., Rydberg states in fluorinated benzenes; hexa-, penta-, and mono- fluorobenzene, Chem. Phys. Lett., 1971, 12, 269. [all data]

Gilbert and Sandorfy, 1971
Gilbert, R.; Sandorfy, C., The vacuum-ultraviolet spectrum of fluorobenzene, Chem. Phys. Lett., 1971, 9, 121. [all data]

Momigny, Goffart, et al., 1968
Momigny, J.; Goffart, C.; D'Or, L., Photoionization studies by total ionization measurements. I. Benzene and its monohalogeno derivatives, Intern. J. Mass Spectrom. Ion Phys., 1968, 1, 53. [all data]

Clark and Frost, 1967
Clark, I.D.; Frost, D.C., A study of the energy levels in benzene and some fluorobenzenes by photoelectron spectroscopy, J. Am. Chem. Soc., 1967, 89, 244. [all data]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [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]

Hammond, Price, et al., 1950
Hammond, V.J.; Price, W.C.; Teegan, J.P.; Walsh, A.D., The absorption spectra of some substituted benzenes and naphthalenes in the vacuum ultra-violet, Faraday Discuss. Chem. Soc., 1950, 9, 53. [all data]

Sell and Kupperman, 1978
Sell, J.A.; Kupperman, A., Angular distributions in the photoelectron spectra of benzene and its monohalogenated derivatives, Chem. Phys., 1978, 33, 367. [all data]

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 «pi» 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]

Dallos, Sisak, et al., 2000
Dallos, A.; Sisak, A.; Kulcsár, Z.; Kováts, E., Pair-wise interactions by gas chromatography VII. Interaction free enthalpies of solutes with secondary alcohol groups, J. Chromatogr. A, 2000, 904, 2, 211-242, https://doi.org/10.1016/S0021-9673(00)00908-0 . [all data]

Righezza, Hassani, et al., 1996
Righezza, M.; Hassani, A.; Meklati, B.Y.; Chrétien, J.R., Quantitative structure-retention relationships (QSRR) of congeneric aromatics series studied on phenyl OV phases in gas chromatography, J. Chromatogr. A, 1996, 723, 1, 77-91, https://doi.org/10.1016/0021-9673(95)00816-0 . [all data]

Hassani and Meklati, 1992
Hassani, A.; Meklati, B.Y., Gas chromatographic behaviour of monosubstituted benzenes, benzaldehydes and acetophenones on OV polymethylphenyl-silicone stationary phases, Chromatographia, 1992, 33, 5/6, 267-271, https://doi.org/10.1007/BF02276193 . [all data]

Reddy, Dutoit, et al., 1992
Reddy, K.S.; Dutoit, J.-Cl.; Kovats, E. sz., Pair-wise interactions by gas chromatography. I. Interaction free enthalpies of solutes with non-associated primary alcohol groups, J. Chromatogr., 1992, 609, 1-2, 229-259, https://doi.org/10.1016/0021-9673(92)80167-S . [all data]

Dutoit, 1991
Dutoit, J., Gas chromatographic retention behaviour of some solutes on structurally similar polar and non-polar stationary phases, J. Chromatogr., 1991, 555, 1-2, 191-204, https://doi.org/10.1016/S0021-9673(01)87179-X . [all data]

Evans and Haken, 1987
Evans, M.B.; Haken, J.K., Dispersion and selectivity indices of the halogenated derivatives of cyclohexane, benzene and anisole, J. Chromatogr., 1987, 389, 240-244, https://doi.org/10.1016/S0021-9673(01)94428-0 . [all data]

Haken and Vernon, 1986
Haken, J.K.; Vernon, F., Gas chromatography of halogenated derivatives of cyclohexane, benzene and anisole, J. Chromatogr., 1986, 361, 57-61, https://doi.org/10.1016/S0021-9673(01)86893-X . [all data]

Oszczapowicz, Osek, et al., 1984
Oszczapowicz, J.; Osek, J.; Dolecka, E., Retention indices of dimethylformamidines, dimethylacetamidines and tetramethylguanidines on a non-polar column, J. Chromatogr., 1984, 315, 95-100, https://doi.org/10.1016/S0021-9673(01)90727-7 . [all data]

Riedo, Fritz, et al., 1976
Riedo, F.; Fritz, D.; Tarján, G.; Kováts, E.Sz., A tailor-made C87 hydrocarbon as a possible non-polar standard stationary phase for gas chromatography, J. Chromatogr., 1976, 126, 63-83, https://doi.org/10.1016/S0021-9673(01)84063-2 . [all data]

Vernon and Edwards, 1975
Vernon, F.; Edwards, G.T., Gas-liquid chromatography on fluorinated stationary phases. I. Hydrocarbons and fluorocarbons, J. Chromatogr., 1975, 110, 1, 73-80, https://doi.org/10.1016/S0021-9673(00)91212-3 . [all data]

Wehrli and Kováts, 1959
Wehrli, A.; Kováts, E., Gas-chromatographische Charakterisierung ogranischer Verbindungen. Teil 3: Berechnung der Retentionsindices aliphatischer, alicyclischer und aromatischer Verbindungen, Helv. Chim. Acta, 1959, 7, 7, 2709-2736, https://doi.org/10.1002/hlca.19590420745 . [all data]

Jalali-Heravi and Garkani-Nejad, 1993
Jalali-Heravi, M.; Garkani-Nejad, Z., Prediction of gas chromatographic retention indices of some benzene derivatives, J. Chromatogr., 1993, 648, 2, 389-393, https://doi.org/10.1016/0021-9673(93)80421-4 . [all data]

Engel and Ratel, 2007
Engel, E.; Ratel, J., Correction of the data generated by mass spectrometry analyses of biological tissues: Application to food authentication, J. Chromatogr. A, 2007, 1154, 1-2, 331-341, https://doi.org/10.1016/j.chroma.2007.02.012 . [all data]

Deport, Ratel, et al., 2006
Deport, C.; Ratel, J.; Berdagué, J.-L.; Engel, E., Comprehensive combinatory standard correction: A calibration method for handling instrumental drifts of gas chromatography-mass spectrometry systems, J. Chromatogr. A, 2006, 1116, 1-2, 248-258, https://doi.org/10.1016/j.chroma.2006.03.092 . [all data]

Censullo, Jones, et al., 2003
Censullo, A.C.; Jones, D.R.; Wills, M.T., Speciation of the volatile organic compounds (VOCs) in solventborne aerosol coatings by solid phase microextraction-gas chromatography, J. Coat. Technol., 2003, 75, 936, 47-53, https://doi.org/10.1007/BF02697922 . [all data]

Gautzsch and Zinn, 1996
Gautzsch, R.; Zinn, P., Use of incremental models to estimate the retention indexes of aromatic compounds, Chromatographia, 1996, 43, 3/4, 163-176, https://doi.org/10.1007/BF02292946 . [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]

Buchman, Cao, et al., 1984
Buchman, O.; Cao, G.-Y.; Peng, C.T., Structure assignment by retention index in gas-liquid radiochromatography of substituted cyclohexenes, J. Chromatogr., 1984, 312, 75-90, https://doi.org/10.1016/S0021-9673(01)92765-7 . [all data]

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

Ebrahimi and Hadjmohammadi, 2006
Ebrahimi, P.; Hadjmohammadi, M.R., Simultaneous modeling of the Kovats retention indices on phenyl OV stationary phases with different polarity using MLR and ANN, QSAR Comb. Sci., 2006, 25, 10, 836-845, https://doi.org/10.1002/qsar.200530145 . [all data]

Sorimachi, Tanabe, et al., 1995
Sorimachi, J.; Tanabe, A.; Mitobe, H.; Kuniaki, K.; Masaaki, S., Programmed temperature retention indices for volatile organic compounds on headspace GC/MS analysis, Niigata-ken Eisei Kogai Kenkyusho Nenpo, 1995, 11, 75-79. [all data]


Notes

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