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Benzene, chloro-

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Gas phase thermochemistry data

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

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

Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafgas13.01kcal/molCcrPlatonov and Simulin, 1985 

Condensed phase thermochemistry data

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

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

Data compiled as indicated in comments:
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
Deltafliquid2.74 ± 0.25kcal/molCcrKolesov, Tomareva, et al., 1967Reanalyzed by Cox and Pilcher, 1970, Original value = 2.82 kcal/mol; ALS
Deltafliquid2.55 ± 0.19kcal/molCcbHubbard, Knowlton, et al., 1954ALS
Quantity Value Units Method Reference Comment
Deltacliquid-743.9 ± 0.2kcal/molCcrPlatonov and Simulin, 1985ALS
Deltacliquid-743.48 ± 0.24kcal/molCcrKolesov, Tomareva, et al., 1967ALS
Deltacliquid-743.04 ± 0.19kcal/molCcbHubbard, Knowlton, et al., 1954ALS
Deltacliquid-743.7 ± 2.0kcal/molCcbSmith, Bjellerup, et al., 1953Reanalyzed by Cox and Pilcher, 1970, Original value = -742.64 kcal/mol; ALS
Quantity Value Units Method Reference Comment
liquid47.20cal/mol*KN/AStull, 1937Extrapolation below 91 K, 44.02 J/mol*K.; DH

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
36.35298.15Shehatta, 1993DH
36.754298.15Perez-Casas, Aicart, et al., 1988DH
35.99303.15Reddy, 1986T = 303.15, 313.15 K.; DH
36.0390298.15Fortier and Benson, 1977DH
35.30298.Deshpande and Bhatagadde, 1971T = 298 to 318 K.; DH
37.60305.6Phillip, 1939DH
35.870298.1Stull, 1937T = 90 to 320 K.; DH
34.80293.2Williams and Daniels, 1925T = 20 to 80°C.; DH
33.70298.von Reis, 1881T = 294 to 425 K.; DH

Constant pressure heat capacity of solid

Cp,solid (cal/mol*K) Temperature (K) Reference Comment
25.41216.8Andrews and Haworth, 1928T = 101 to 217 K. Value is unsmoothed experimental datum.; DH

Reaction thermochemistry data

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

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

Data compiled as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

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

By formula: Cl- + C6H5Cl = (Cl- bullet C6H5Cl)

Quantity Value Units Method Reference Comment
Deltar12.00 ± 0.10kcal/molTDAsSieck, 1985gas phase; B,M
Deltar13.6 ± 1.0kcal/molIMRELarson and McMahon, 1984gas phase; B,B,M
Deltar12.6kcal/molPHPMSPaul and Kebarle, 1991gas phase; from Ph. D. thesis of S. Chowdhury, Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar20.cal/mol*KN/APaul and Kebarle, 1991gas phase; from Ph. D. thesis of S. Chowdhury, Entropy change calculated or estimated; M
Deltar16.5cal/mol*KPHPMSSieck, 1985gas phase; M
Deltar22.4cal/mol*KN/ALarson and McMahon, 1984gas phase; switching reaction(Cl-)t-C4H9OH, Entropy change calculated or estimated; French, Ikuta, et al., 1982; M
Quantity Value Units Method Reference Comment
Deltar7.10 ± 0.20kcal/molTDAsSieck, 1985gas phase; B
Deltar6.9 ± 1.0kcal/molIMRELarson and McMahon, 1984gas phase; B,B,M
Deltar6.50kcal/molTDEqFrench, Ikuta, et al., 1982gas phase; B

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
6.6300.PHPMSPaul and Kebarle, 1991gas phase; from Ph. D. thesis of S. Chowdhury, Entropy change calculated or estimated; M
6.5300.PHPMSFrench, Ikuta, et al., 1982gas phase; M

C6H4Cl- + Hydrogen cation = Benzene, chloro-

By formula: C6H4Cl- + H+ = C6H5Cl

Quantity Value Units Method Reference Comment
Deltar391.0 ± 1.9kcal/molBranWenthold and Squires, 1995gas phase; B
Deltar390.2 ± 2.1kcal/molG+TSWenthold and Squires, 1994gas phase; between furan, pyridine; B
Deltar390.2 ± 2.1kcal/molG+TSWenthold, Paulino, et al., 1991gas phase; Between H2O, furan. Wenthold and Squires, 1994 indicates isomerization occuring.; B
Quantity Value Units Method Reference Comment
Deltar382.8 ± 2.0kcal/molH-TSWenthold and Squires, 1995gas phase; B
Deltar382.0 ± 2.0kcal/molIMRBWenthold and Squires, 1994gas phase; between furan, pyridine; B
Deltar382.0 ± 2.0kcal/molIMRBWenthold, Paulino, et al., 1991gas phase; Between H2O, furan. Wenthold and Squires, 1994 indicates isomerization occuring.; B

C6H4Cl- + Hydrogen cation = Benzene, chloro-

By formula: C6H4Cl- + H+ = C6H5Cl

Quantity Value Units Method Reference Comment
Deltar394.4 ± 1.3kcal/molBranWenthold and Squires, 1995gas phase; B
Deltar389.7 ± 2.1kcal/molG+TSWenthold and Squires, 1994gas phase; between furan, pyridine; B
Deltar389.7 ± 2.1kcal/molG+TSWenthold, Paulino, et al., 1991gas phase; Between H2O, furan. Wenthold and Squires, 1994 indicates isomerization occuring.; B
Quantity Value Units Method Reference Comment
Deltar386.6 ± 1.4kcal/molH-TSWenthold and Squires, 1995gas phase; B
Deltar382.0 ± 2.0kcal/molIMRBWenthold and Squires, 1994gas phase; between furan, pyridine; B
Deltar382.0 ± 2.0kcal/molIMRBWenthold, Paulino, et al., 1991gas phase; Between H2O, furan. Wenthold and Squires, 1994 indicates isomerization occuring.; B

C6H4Cl- + Hydrogen cation = Benzene, chloro-

By formula: C6H4Cl- + H+ = C6H5Cl

Quantity Value Units Method Reference Comment
Deltar386.7 ± 2.1kcal/molG+TSAndrade and Riveros, 1996gas phase; B
Deltar388.2 ± 2.0kcal/molBranWenthold and Squires, 1995gas phase; B
Deltar387.7 ± 3.1kcal/molG+TSWenthold, Paulino, et al., 1991gas phase; Between PhF, furan; B
Quantity Value Units Method Reference Comment
Deltar378.5 ± 2.0kcal/molIMREAndrade and Riveros, 1996gas phase; B
Deltar380.0 ± 2.1kcal/molH-TSWenthold and Squires, 1995gas phase; B
Deltar379.5 ± 3.0kcal/molIMRBWenthold, Paulino, et al., 1991gas phase; Between PhF, furan; B
Deltar379.0 ± 5.0kcal/molIMRBBartmess and McIver Jr., 1979gas phase; Between H2O, MeOH; B

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

By formula: Br- + C6H5Cl = (Br- bullet C6H5Cl)

Quantity Value Units Method Reference Comment
Deltar11.1 ± 1.8kcal/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
Deltar20.cal/mol*KN/APaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar2.6 ± 1.0kcal/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° (kcal/mol) T (K) Method Reference Comment
2.6423.PHPMSPaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M

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

By formula: C6H7N+ + C6H5Cl = (C6H7N+ bullet C6H5Cl)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar11.7kcal/molPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar26.cal/mol*KN/AMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
4.0297.PHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M

C9H12+ + Benzene, chloro- = (C9H12+ bullet Benzene, chloro-)

By formula: C9H12+ + C6H5Cl = (C9H12+ bullet C6H5Cl)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar11.4kcal/molPHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar27.cal/mol*KN/AMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; Entropy change calculated or estimated; M

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
2.9300.PHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; Entropy change calculated or estimated; M

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

By formula: NO- + C6H5Cl = (NO- bullet C6H5Cl)

Quantity Value Units Method Reference Comment
Deltar38.5kcal/molICRReents and Freiser, 1981gas phase; switching reaction,Thermochemical ladder(NO+)C2H5OH, Entropy change calculated or estimated; Farid and McMahon, 1978; M

Benzene, chloro- + 1-Chloro-2,4-diisopropylbenzene = Benzene, 1-chloro-2-(1-methylethyl)- + Benzene, 1-chloro-4-(1-methylethyl)-

By formula: C6H5Cl + C12H17Cl = C9H11Cl + C9H11Cl

Quantity Value Units Method Reference Comment
Deltar-0.20 ± 0.10kcal/molEqkNesterova, Rozhnov, et al., 1985liquid phase; ALS

Benzene, chloro- + 2,4-Di-t-butyl chlorobenzene = 1-Chloro-4-(1,1-dimethylethyl)benzene + Benzene, 1-tert-butyl-2-chloro-

By formula: C6H5Cl + C14H21Cl = C10H13Cl + C10H13Cl

Quantity Value Units Method Reference Comment
Deltar-0.06 ± 0.17kcal/molEqkKovzel, Nesterova, et al., 1981liquid phase; ALS

Benzene, 1-chloro-2-(1-methylethyl)- + Benzene = Benzene, chloro- + Benzene, (1-methylethyl)-

By formula: C9H11Cl + C6H6 = C6H5Cl + C9H12

Quantity Value Units Method Reference Comment
Deltar-0.14 ± 0.10kcal/molEqkNesterova, Rozhnov, et al., 1985liquid phase; ALS

Benzene, chloro- + Benzene, 1-chloro-3,5-bis(1,1-dimethylethyl)- = 2m-Tert-butyl chlorobenzene

By formula: C6H5Cl + C14H21Cl = 2C10H13Cl

Quantity Value Units Method Reference Comment
Deltar0. ± 0.02kcal/molEqkKovzel, Nesterova, et al., 1981liquid phase; ALS

Benzene + Chlorine = Benzene, chloro- + Hydrogen chloride

By formula: C6H6 + Cl2 = C6H5Cl + HCl

Quantity Value Units Method Reference Comment
Deltar-32.0kcal/molCmKirkbride, 1956liquid phase; ALS

References

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

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

Platonov and Simulin, 1985
Platonov, V.A.; Simulin, Yu.N., Determination of the standard enthalpies of formation of polychlorobenzenes. III. The standard enthalpies of formation of mono-1,2,4- and 1,3,5-tri-, and 1,2,3,4- and 1,2,3,5-tetrachlorobenzenes, Russ. J. Phys. Chem. (Engl. Transl.), 1985, 59, 179-181. [all data]

Kolesov, Tomareva, et al., 1967
Kolesov, V.P.; Tomareva, E.M.; Skuratov, S.M.; Alekhin, S.P., Calorimeter having a rotating bomb for determining heats of combustion of chlorinated organic compounds, Russ. J. Phys. Chem. (Engl. Transl.), 1967, 41, 817-820. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Hubbard, Knowlton, et al., 1954
Hubbard, W.N.; Knowlton, J.W.; Huffman, H.M., Combustion calorimetry of organic chlorine compounds. Heats of combustion of chlorobenzene, the dichlorobenzenes and o- and p-chloroethylbenzene, J. Phys. Chem., 1954, 58, 396. [all data]

Smith, Bjellerup, et al., 1953
Smith, L.; Bjellerup, L.; Krook, S.; Westermark, H., Heats of combustion of organic chloro compounds determined by the "quartz wool" method, Acta Chem. Scand., 1953, 7, 65. [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]

Shehatta, 1993
Shehatta, I., Heat capacity at constant pressure of some halogen compounds, Thermochim. Acta, 1993, 213, 1-10. [all data]

Perez-Casas, Aicart, et al., 1988
Perez-Casas, S.; Aicart, E.; Trojo, L.M.; Costas, M., Excess heat capacity. Chlorobenzene-2,2,4,4,6,8,8-heptamethylnonane, Int. Data Ser., Sel. Data Mixtures, 1988, (2)A, 123. [all data]

Reddy, 1986
Reddy, K.S., Isentropic compressibilities of binary liquid mixtures at 303.15 and 313.15 K, J. Chem. Eng. Data, 1986, 31, 238-240. [all data]

Fortier and Benson, 1977
Fortier, J.-L.; Benson, G.C., Excess heat capacities of binary mixtures of tetrachloromethane witlh some aromatic liquids at 298.15 K, J. Chem. Thermodynam., 1977, 9, 1181-1188. [all data]

Deshpande and Bhatagadde, 1971
Deshpande, D.D.; Bhatagadde, L.G., Heat capacities at constant volume, free volumes, and rotational freedom in some liquids, Aust. J. Chem., 1971, 24, 1817-1822. [all data]

Phillip, 1939
Phillip, N.M., Adiabatic and isothermal compressibilities of liquids, Proc. Indian Acad. Sci., 1939, A9, 109-120. [all data]

Williams and Daniels, 1925
Williams, J.W.; Daniels, F., The specific heats of binary mixtures, J. Am. Chem. Soc., 1925, 47, 1490-1503. [all data]

von Reis, 1881
von Reis, M.A., Die specifische Wärme flüssiger organischer Verbindungen und ihre Beziehung zu deren Moleculargewicht, Ann. Physik [3], 1881, 13, 447-464. [all data]

Andrews and Haworth, 1928
Andrews, D.H.; Haworth, E., An application of the rule of Dulong and Petit to molecules, J. Am. Chem. Soc., 1928, 50, 2998-3002. [all data]

Sieck, 1985
Sieck, L.W., Thermochemistry of Solvation of NO2- and C6H5NO2- by Polar Molecules in the Vapor Phase. Comparison with Cl- and Variation with Ligand Structure., J. Phys. Chem., 1985, 89, 25, 5552, https://doi.org/10.1021/j100271a049 . [all data]

Larson and McMahon, 1984
Larson, J.W.; McMahon, T.B., Gas phase negative ion chemistry of alkylchloroformates, Can. J. Chem., 1984, 62, 675. [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]

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]

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]

Wenthold and Squires, 1994
Wenthold, P.G.; Squires, R.R., Gas-phase properties and reactivity of the acetate radical anion. Determination of the C-H bond strengths in acetic acid and acetate ion, J. Am. Chem. Soc., 1994, 116, 26, 11890, https://doi.org/10.1021/ja00105a032 . [all data]

Wenthold, Paulino, et al., 1991
Wenthold, P.G.; Paulino, J.A.; Squires, R.R., The Absolute Heats of Formation of ortho-Benzyne, meta-Benzyne, and para-Benzyne, J. Am. Chem. Soc., 1991, 113, 19, 7414, https://doi.org/10.1021/ja00019a044 . [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]

Bartmess and McIver Jr., 1979
Bartmess, J.E.; McIver Jr., The Gas Phase Acidity Scale in Gas Phase Ion Chemistry, Gas Phase Ion Chemistry, V. 2, M.T. Bowers, Ed., Academic Press, NY, 1979, Ch. 11, Elsevier, 1979. [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]

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]

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]

Nesterova, Rozhnov, et al., 1985
Nesterova, T.N.; Rozhnov, A.M.; Malova, T.N.; Kovzel, E.N., Molar enthalpies of formation of isopropylchlorobenzenes derived from equilibrium measurements, J. Chem. Thermodyn., 1985, 17, 649-656. [all data]

Kovzel, Nesterova, et al., 1981
Kovzel, E.N.; Nesterova, T.N.; Rozhnov, A.M.; Kartavtseva, T.A., Study of equilibrium in in the chlorobenzene-butylchlorobenzenes systems, Termodin. Organ. Soedin., 1981, 65-68. [all data]

Kirkbride, 1956
Kirkbride, F.W., The heats of chlorination of some hydrocarbons and their chloro-derivatives, J. Appl. Chem., 1956, 6, 11-21. [all data]


Notes

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