Benzene, chloropentafluoro-
- Formula: C6ClF5
- Molecular weight: 202.509
- IUPAC Standard InChIKey: KGCDGLXSBHJAHZ-UHFFFAOYSA-N
- CAS Registry Number: 344-07-0
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: Chloropentafluorobenzene; Pentafluorochlorobenzene; Pentafluorophenyl chloride; Chloroperfluorobenzene; 1-Chloro-2,3,4,5,6-pentafluorobenzene
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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 |
---|---|---|---|---|---|
ΔfH°gas | -193.50 ± 0.48 | kcal/mol | Ccr | Cox, Gundry, et al., 1969 |
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 |
---|---|---|---|---|---|
ΔfH°liquid | -203.3 ± 0.53 | kcal/mol | Ccr | Cox, Gundry, et al., 1969 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -580.47 ± 0.48 | kcal/mol | Ccr | Cox, Gundry, et al., 1969 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 72.560 | cal/mol*K | N/A | Paukov and Glukhikh, 1969 | DH |
S°liquid | 71.87 | cal/mol*K | N/A | Andon, Counsell, et al., 1968 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
53.339 | 298.15 | Paukov and Glukhikh, 1969 | T = 13 to 303 K.; DH |
52.92 | 298.15 | Andon, Counsell, et al., 1968 | T = 12 to 395 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
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 390. | K | N/A | PCR Inc., 1990 | BS |
Tboil | 391.2 | K | N/A | Majer and Svoboda, 1985 | |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 257.29 | K | N/A | Paukov and Glukhikh, 1969, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC |
Ttriple | 257.49 | K | N/A | Andon, Counsell, et al., 1968, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 571. | K | N/A | Majer and Svoboda, 1985 | |
Tc | 569.9 | K | N/A | Skripov and Muratov, 1977 | TRC |
Tc | 570.81 | K | N/A | Hales and Townsend, 1974 | Uncertainty assigned by TRC = 0.05 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 31.48 | atm | N/A | Skripov and Muratov, 1977 | Vis, pc by extrapolation of V; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 2.661 | mol/l | N/A | Hales and Townsend, 1974 | Uncertainty assigned by TRC = 0.0026 mol/l; Liquid density determined by magnetically balanced float up to 490 K, see J.L.Hales, 1970-128. Critical D by equation due to Riedel.; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 9.82 | kcal/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 9.87 | kcal/mol | N/A | Basarová and Svoboda, 1991 | Based on data from 290. to 550. K.; AC |
ΔvapH° | 9.75 ± 0.1 | kcal/mol | V | Cox, Gundry, et al., 1969 | ALS |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
395.7 | 0.987 | Weast and Grasselli, 1989 | BS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
8.308 | 391.2 | N/A | Majer and Svoboda, 1985 | |
9.01 | 363. | A | Stephenson and Malanowski, 1987 | Based on data from 348. to 402. K.; AC |
9.56 | 322. | A | Stephenson and Malanowski, 1987 | Based on data from 307. to 417. K. See also Ambrose, 1968.; AC |
9.01 ± 0.02 | 349. | N/A | Andon, Counsell, et al., 1968, 3 | AC |
8.70 ± 0.02 | 369. | N/A | Andon, Counsell, et al., 1968, 3 | AC |
8.32 ± 0.02 | 391. | N/A | Andon, Counsell, et al., 1968, 3 | AC |
8.308 ± 0.002 | 391.1 | C | Andon, Counsell, et al., 1968 | Hfusion=8.36±0.01 kJ/mol; ALS |
8.41 | 418. | EB | Evans and Tiley, 1966 | Based on data from 403. to 547. K.; AC |
Enthalpy of vaporization
ΔvapH =
A exp(-βTr) (1 − Tr)β
ΔvapH =
Enthalpy of vaporization (at saturation pressure)
(kcal/mol)
Tr = reduced temperature (T / Tc)
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Temperature (K) | A (kcal/mol) | β | Tc (K) | Reference | Comment |
---|---|---|---|---|---|
349. to 391. | 14.11 | 0.2876 | 571. | Majer and Svoboda, 1985 |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
308.73 to 417.28 | 4.18695 | 1388.461 | -59.485 | Ambrose, 1968, 2 | Coefficents calculated by NIST from author's data. |
403.44 to 546.44 | 4.72488 | 1850.097 | 2.664 | Evans and Tiley, 1966, 2 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
2.00 | 257.5 | Domalski and Hearing, 1996 | See also Andon, Counsell, et al., 1968, 3.; AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
4.551 | 191. | Domalski and Hearing, 1996 | CAL |
0.958 | 245. | ||
7.756 | 257.5 |
Enthalpy of phase transition
ΔHtrs (kcal/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.2971 | 191.2 | crystaline, II | crystaline, I | Paukov and Glukhikh, 1969 | DH |
2.007 | 257.29 | crystaline, I | liquid | Paukov and Glukhikh, 1969 | DH |
0.8690 | 191. | crystaline, III | crystaline, II | Andon, Counsell, et al., 1968 | Entropy change reported as 17.91 J/mol*K from integration of excess heat capacity. Value given assumes isothermal transition.; DH |
0.235 | 245. | crystaline, II | crystaline, I | Andon, Counsell, et al., 1968 | DH |
1.997 | 257.49 | crystaline, I | liquid | Andon, Counsell, et al., 1968 | DH |
Entropy of phase transition
ΔStrs (cal/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
1.55 | 191.2 | crystaline, II | crystaline, I | Paukov and Glukhikh, 1969 | DH |
7.801 | 257.29 | crystaline, I | liquid | Paukov and Glukhikh, 1969 | DH |
4.551 | 191. | crystaline, III | crystaline, II | Andon, Counsell, et al., 1968 | Entropy; DH |
0.958 | 245. | crystaline, II | crystaline, I | Andon, Counsell, et al., 1968 | DH |
7.756 | 257.49 | crystaline, I | liquid | Andon, Counsell, et al., 1968 | DH |
Gas phase ion energetics data
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data evaluated as indicated in comments:
L - Sharon G. Lias
Data compiled as indicated in comments:
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
B - John E. Bartmess
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 9.72 ± 0.14 | eV | N/A | N/A | L |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
0.750 ± 0.080 | N/A | Miller and Viggiano, 2005 | B |
0.82 ± 0.11 | IMRE | Dillow and Kebarle, 1989 | ΔGea(423 K) = -20.3 kcal/mol . Assumed EA entropy = 3.5 eu; B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.72 ± 0.02 | PE | Mohraz, Maier, et al., 1980 | LLK |
10.4 ± 0.1 | EI | Majer and Patrick, 1962 | RDSH |
9.5 | PE | Bieri, Asbrink, et al., 1982 | Vertical value; LBLHLM |
9.94 | PE | Trudell and Price, 1979 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C6F5+ | 15.85 ± 0.05 | Cl | EI | Price and Sapiano, 1974 | LLK |
C6F5+ | 15.9 ± 0.1 | Cl | EI | Majer and Patrick, 1962 | RDSH |
Gas Chromatography
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | OV-101 | 748. | Zenkevich, Eliseenkov, et al., 2006 | Nitrogen, 6. K/min, 240. C @ 10. min; Column length: 25. m; Column diameter: 0.20 mm; Tstart: 60. C |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Cox, Gundry, et al., 1969
Cox, J.D.; Gundry, H.A.; Harrop, D.; Head, A.J.,
Thermodynamic properties of fluorine compounds. 9. Enthalpies of formation of some compounds containing the pentafluorophenyl group,
J. Chem. Thermodyn., 1969, 1, 77-87. [all data]
Paukov and Glukhikh, 1969
Paukov, I.E.; Glukhikh, L.K.,
The true heat capacity over the range 13-300K and the entropy and enthalpy of chloropentafluorobenzene,
Zhur. Fiz. Khim., 1969, 43, 1350-1352. [all data]
Andon, Counsell, et al., 1968
Andon, R.J.L.; Counsell, J.F.; Hales, J.L.; Lees, E.B.; Martin, J.F.,
Thermodynamic properties of fluorine compounds. Part VII. Heat capacity and entropy of pentafluorochelorobenzene and pentafluorophenol,
J. Chem. Soc. A, 1968, 2357-2361. [all data]
PCR Inc., 1990
PCR Inc.,
Research Chemicals Catalog 1990-1991, PCR Inc., Gainesville, FL, 1990, 1. [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]
Paukov and Glukhikh, 1969, 2
Paukov, I.E.; Glukhikh, L.K.,
The true heat capacity over the range 13-300 k and the entropy and enthalpy of chloropentafluorobenzene,
Zh. Fiz. Khim., 1969, 43, 1350-2. [all data]
Andon, Counsell, et al., 1968, 2
Andon, R.J.L.; Counsell, J.F.; Hales, J.L.; Lees, E.B.; Martin, J.F.,
Thermodynamic properties of fluorine compounds: vii heat capacity and entropy of pentafluorochlorobenzene and pentafluorophenol,
J. Chem. Soc. A, 1968, 1968, 2357-61. [all data]
Skripov and Muratov, 1977
Skripov, V.P.; Muratov, G.N.,
The surface tensions of liquids and their interpretation by the method of thermodynamic similarity.,
Russ. J. Phys. Chem. (Engl. Transl.), 1977, 51, 806-8. [all data]
Hales and Townsend, 1974
Hales, J.L.; Townsend, R.,
Liquid Densities from 293 to 490 K of Eight Fluorinated Aromatic Comp.,
J. Chem. Thermodyn., 1974, 6, 111-6. [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]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [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]
Ambrose, 1968
Ambrose, D.,
Thermodynamic properties of fluorine compounds. Part V. Vapour pressures of pentafluorobenzene, chloropentafluorobenzene, 2,3,4,5,6-pentafluorotoluene, and pentafluorophenol,
J. Chem. Soc., A, 1968, 1381, https://doi.org/10.1039/j19680001381
. [all data]
Andon, Counsell, et al., 1968, 3
Andon, R.J.L.; Counsell, J.F.; Hales, J.L.; Lees, E.B.; Martin, J.F.,
Thermodynamic properties of fluorine compounds. Part VII. Heat capacity and entropy of pentafluorochlorobenzene and pentafluorophenol,
J. Chem. Soc., A, 1968, 2357, https://doi.org/10.1039/j19680002357
. [all data]
Evans and Tiley, 1966
Evans, F.D.; Tiley, P.F.,
Vapour pressures and critical constants of hexafluoro-, pentafluoro-, chloropentafluoro-, and bromopentafluoro-benzene,
J. Chem. Soc., B:, 1966, 134, https://doi.org/10.1039/j29660000134
. [all data]
Ambrose, 1968, 2
Ambrose, D.,
Thermodynamic Properties of Fluorine Compounds. Part V. Vapour Pressures of Pentafluorobenzene, Chloropentafluorobenzene, 2,3,4,5,6-Pentafluorotoluene, and Pentafluorophenol,
J. Chem. Soc. A:, 1968, 1381-1383, https://doi.org/10.1039/j19680001381
. [all data]
Evans and Tiley, 1966, 2
Evans, F.D.; Tiley,
Vapour Pressures and Critical Constants of Hexafluoro-, Pentafluoro-, Chloropentafluoro-, and Bromopentafluoro-benzene,
J. Chem. Soc. B:, 1966, 134-136, https://doi.org/10.1039/j29660000134
. [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]
Miller and Viggiano, 2005
Miller, T.M.; Viggiano, A.A.,
Electron attachment and detachment: C6F5Cl, C6F5Br, and C6F5I and the electron affinity of C6F5Cl,
Phys. Rev. A, 2005, 71, 1, 012702, https://doi.org/10.1103/PhysRevA.71.012702
. [all data]
Dillow and Kebarle, 1989
Dillow, G.W.; Kebarle, P.,
Substituent Effects on the Electron Affinities of Perfluorobenzenes C6F5X,
J. Am. Chem. Soc., 1989, 111, 15, 5592, https://doi.org/10.1021/ja00197a014
. [all data]
Mohraz, Maier, et al., 1980
Mohraz, M.; Maier, J.P.; Heilbronner, E.,
He(I α) and He(Iα) photoelectron spectra of fluorinated chloro- and bromobenzenes,
J. Electron Spectrosc. Relat. Phenom., 1980, 19, 429. [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]
Bieri, Asbrink, et al., 1982
Bieri, G.; Asbrink, L.; Von Niessen, W.,
30.4-nm He(II) photoelectron spectra of organic molecules,
J. Electron Spectrosc. Relat. Phenom., 1982, 27, 129. [all data]
Trudell and Price, 1979
Trudell, B.C.; Price, S.J.W.,
The ultraviolet photoelectron spectra of C6F5X compounds, X=(F, Cl, Br, I, H, CH3),
Can. J. Chem., 1979, 57, 2256. [all data]
Price and Sapiano, 1974
Price, S.J.W.; Sapiano, H.J.,
C6F5X bond dissociation energies: determination from appearance potential measurements and correlation with thermochemical data,
Can. J. Chem., 1974, 52, 4109. [all data]
Zenkevich, Eliseenkov, et al., 2006
Zenkevich, I.G.; Eliseenkov, E.V.; Kasatochkin, A.N.,
Application of Retention Indices in GC-MS Identification of Halogenated Organic Compounds,
Mass Spectromery (Rus.), 2006, 3, 2, 131-140. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid EA Electron affinity IE (evaluated) Recommended ionization energy Pc Critical pressure S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tc Critical temperature Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions ρc Critical density - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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