Benzene, chloro-

Formula: C₆H₅Cl
Molecular weight: 112.557
IUPAC Standard InChI: InChI=1S/C6H5Cl/c7-6-4-2-1-3-5-6/h1-5H
IUPAC Standard InChIKey: MVPPADPHJFYWMZ-UHFFFAOYSA-N
CAS Registry Number: 108-90-7
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
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Other names: Chlorobenzene; Monochlorobenzene; MCB; Phenyl Chloride; Benzene chloride; Chlorbenzene; Chlorobenzol; Monochlorbenzene; Chloorbenzeen; Chlorbenzol; Chlorobenzen; Chlorobenzene, mono-; Clorobenzene; Monochloorbenzeen; Monochlorbenzol; Monoclorobenzene; NCI-C54886; Chlorobenzenu; UN 1134; Abluton T30; CP 27; IP Carrier T 40; NSC 8433; Tetrosin SP
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Reaction thermochemistry data

Go To: Top, References, Notes

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

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Individual Reactions

+ Benzene, chloro- = ( • )

By formula: Cl^- + C₆H₅Cl = (Cl^- • C₆H₅Cl)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	50.21 ± 0.42	kJ/mol	TDAs	Sieck, 1985	gas phase; B,M
Δ_rH°	56.9 ± 4.2	kJ/mol	IMRE	Larson and McMahon, 1984	gas phase; B,B,M
Δ_rH°	52.7	kJ/mol	PHPMS	Paul and Kebarle, 1991	gas phase; from Ph. D. thesis of S. Chowdhury, Entropy change calculated or estimated; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	84.	J/mol*K	N/A	Paul and Kebarle, 1991	gas phase; from Ph. D. thesis of S. Chowdhury, Entropy change calculated or estimated; M
Δ_rS°	69.0	J/mol*K	PHPMS	Sieck, 1985	gas phase; M
Δ_rS°	93.7	J/mol*K	N/A	Larson and McMahon, 1984	gas phase; switching reaction(Cl-)t-C4H9OH, Entropy change calculated or estimated; French, Ikuta, et al., 1982; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	29.7 ± 0.84	kJ/mol	TDAs	Sieck, 1985	gas phase; B
Δ_rG°	29. ± 4.2	kJ/mol	IMRE	Larson and McMahon, 1984	gas phase; B,B,M
Δ_rG°	27.2	kJ/mol	TDEq	French, Ikuta, et al., 1982	gas phase; B

Free energy of reaction

Δ_rG° (kJ/mol)	T (K)	Method	Reference	Comment
28.	300.	PHPMS	Paul and Kebarle, 1991	gas phase; from Ph. D. thesis of S. Chowdhury, Entropy change calculated or estimated; M
27.	300.	PHPMS	French, Ikuta, et al., 1982	gas phase; M

C₆H₄Cl^- + = Benzene, chloro-

By formula: C₆H₄Cl^- + H⁺ = C₆H₅Cl

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1636. ± 7.9	kJ/mol	Bran	Wenthold and Squires, 1995	gas phase; B
Δ_rH°	1633. ± 8.8	kJ/mol	G+TS	Wenthold and Squires, 1994	gas phase; between furan, pyridine; B
Δ_rH°	1633. ± 8.8	kJ/mol	G+TS	Wenthold, Paulino, et al., 1991	gas phase; Between H2O, furan. Wenthold and Squires, 1994 indicates isomerization occuring.; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	1602. ± 8.4	kJ/mol	H-TS	Wenthold and Squires, 1995	gas phase; B
Δ_rG°	1598. ± 8.4	kJ/mol	IMRB	Wenthold and Squires, 1994	gas phase; between furan, pyridine; B
Δ_rG°	1598. ± 8.4	kJ/mol	IMRB	Wenthold, Paulino, et al., 1991	gas phase; Between H2O, furan. Wenthold and Squires, 1994 indicates isomerization occuring.; B

C₆H₄Cl^- + = Benzene, chloro-

By formula: C₆H₄Cl^- + H⁺ = C₆H₅Cl

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1650. ± 5.4	kJ/mol	Bran	Wenthold and Squires, 1995	gas phase; B
Δ_rH°	1631. ± 8.8	kJ/mol	G+TS	Wenthold and Squires, 1994	gas phase; between furan, pyridine; B
Δ_rH°	1631. ± 8.8	kJ/mol	G+TS	Wenthold, Paulino, et al., 1991	gas phase; Between H2O, furan. Wenthold and Squires, 1994 indicates isomerization occuring.; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	1618. ± 5.9	kJ/mol	H-TS	Wenthold and Squires, 1995	gas phase; B
Δ_rG°	1598. ± 8.4	kJ/mol	IMRB	Wenthold and Squires, 1994	gas phase; between furan, pyridine; B
Δ_rG°	1598. ± 8.4	kJ/mol	IMRB	Wenthold, Paulino, et al., 1991	gas phase; Between H2O, furan. Wenthold and Squires, 1994 indicates isomerization occuring.; B

C₆H₄Cl^- + = Benzene, chloro-

By formula: C₆H₄Cl^- + H⁺ = C₆H₅Cl

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1618. ± 8.8	kJ/mol	G+TS	Andrade and Riveros, 1996	gas phase; B
Δ_rH°	1624. ± 8.4	kJ/mol	Bran	Wenthold and Squires, 1995	gas phase; B
Δ_rH°	1622. ± 13.	kJ/mol	G+TS	Wenthold, Paulino, et al., 1991	gas phase; Between PhF, furan; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	1584. ± 8.4	kJ/mol	IMRE	Andrade and Riveros, 1996	gas phase; B
Δ_rG°	1590. ± 8.8	kJ/mol	H-TS	Wenthold and Squires, 1995	gas phase; B
Δ_rG°	1588. ± 13.	kJ/mol	IMRB	Wenthold, Paulino, et al., 1991	gas phase; Between PhF, furan; B
Δ_rG°	1586. ± 21.	kJ/mol	IMRB	Bartmess and McIver Jr., 1979	gas phase; Between H2O, MeOH; B

+ Benzene, chloro- = ( • )

By formula: Br^- + C₆H₅Cl = (Br^- • C₆H₅Cl)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	46.4 ± 7.5	kJ/mol	IMRE	Paul and Kebarle, 1991	gas 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
Δ_rS°	84.	J/mol*K	N/A	Paul and Kebarle, 1991	gas phase; Entropy change calculated or estimated; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	11. ± 4.2	kJ/mol	IMRE	Paul and Kebarle, 1991	gas phase; ΔGaff measured at 303 K, corrected to 423 K, ΔSaff taken as that of PhNO2..Br-; B

Free energy of reaction

Δ_rG° (kJ/mol)	T (K)	Method	Reference	Comment
11.	423.	PHPMS	Paul and Kebarle, 1991	gas phase; Entropy change calculated or estimated; M

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

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

Bond type: Charge transfer bond (positive ion)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	49.0	kJ/mol	PHPMS	Meot-Ner (Mautner) and El-Shall, 1986	gas phase; Entropy change calculated or estimated; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	110.	J/mol*K	N/A	Meot-Ner (Mautner) and El-Shall, 1986	gas phase; Entropy change calculated or estimated; M

Free energy of reaction

Δ_rG° (kJ/mol)	T (K)	Method	Reference	Comment
17.	297.	PHPMS	Meot-Ner (Mautner) and El-Shall, 1986	gas phase; Entropy change calculated or estimated; M

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

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

Bond type: Charge transfer bond (positive ion)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	47.7	kJ/mol	PHPMS	Meot-Ner (Mautner), Hamlet, et al., 1978	gas phase; Entropy change calculated or estimated; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	110.	J/mol*K	N/A	Meot-Ner (Mautner), Hamlet, et al., 1978	gas phase; Entropy change calculated or estimated; M

Free energy of reaction

Δ_rG° (kJ/mol)	T (K)	Method	Reference	Comment
12.	300.	PHPMS	Meot-Ner (Mautner), Hamlet, et al., 1978	gas phase; Entropy change calculated or estimated; M

+ Benzene, chloro- = ( • )

By formula: NO^- + C₆H₅Cl = (NO^- • C₆H₅Cl)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	161.	kJ/mol	ICR	Reents and Freiser, 1981	gas phase; switching reaction,Thermochemical ladder(NO+)C2H5OH, Entropy change calculated or estimated; Farid and McMahon, 1978; M

Benzene, chloro- + = +

By formula: C₆H₅Cl + C₁₂H₁₇Cl = C₉H₁₁Cl + C₉H₁₁Cl

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-0.84 ± 0.42	kJ/mol	Eqk	Nesterova, Rozhnov, et al., 1985	liquid phase; ALS

Benzene, chloro- + = +

By formula: C₆H₅Cl + C₁₄H₂₁Cl = C₁₀H₁₃Cl + C₁₀H₁₃Cl

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-0.25 ± 0.71	kJ/mol	Eqk	Kovzel, Nesterova, et al., 1981	liquid phase; ALS

+ = Benzene, chloro- +

By formula: C₉H₁₁Cl + C₆H₆ = C₆H₅Cl + C₉H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-0.59 ± 0.42	kJ/mol	Eqk	Nesterova, Rozhnov, et al., 1985	liquid phase; ALS

Benzene, chloro- + = 2

By formula: C₆H₅Cl + C₁₄H₂₁Cl = 2C₁₀H₁₃Cl

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	0. ± 0.1	kJ/mol	Eqk	Kovzel, Nesterova, et al., 1981	liquid phase; ALS

+ = Benzene, chloro- +

By formula: C₆H₆ + Cl₂ = C₆H₅Cl + HCl

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-134.	kJ/mol	Cm	Kirkbride, 1956	liquid phase; ALS

References

Go To: Top, Reaction thermochemistry data, Notes

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, Reaction thermochemistry data, References

Symbols used in this document:

T Temperature

Δ_rG° Free energy of reaction at standard conditions

Δ_rH° Enthalpy of reaction at standard conditions

Δ_rS° Entropy of reaction at standard conditions
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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T	Temperature
Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions
Δ_rS°	Entropy of reaction at standard conditions