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
View 3d structure (requires JavaScript / HTML 5)
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
Permanent link for this species. Use this link for bookmarking this species for future reference.
Information on this page:
Other data available:
Data at other public NIST sites:
- Gas Phase Kinetics Database
- X-ray Photoelectron Spectroscopy Database, version 5.0
Options:
- Switch to calorie-based units

Data at NIST subscription sites:

NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

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

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

+ 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
The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
Customer support for NIST Standard Reference Data products.

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