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
The 3d structure may be viewed using Java or Javascript. - 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 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
+
= (
•
)
By formula: Cl- + C6H5Cl = (Cl- • C6H5Cl)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 12.00 ± 0.10 | kcal/mol | TDAs | Sieck, 1985 | gas phase; B,M |
| ΔrH° | 13.6 ± 1.0 | kcal/mol | IMRE | Larson and McMahon, 1984 | gas phase; B,B,M |
| ΔrH° | 12.6 | kcal/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 |
| ΔrS° | 20. | cal/mol*K | N/A | Paul and Kebarle, 1991 | gas phase; from Ph. D. thesis of S. Chowdhury, Entropy change calculated or estimated; M |
| ΔrS° | 16.5 | cal/mol*K | PHPMS | Sieck, 1985 | gas phase; M |
| ΔrS° | 22.4 | cal/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 |
| ΔrG° | 7.10 ± 0.20 | kcal/mol | TDAs | Sieck, 1985 | gas phase; B |
| ΔrG° | 6.9 ± 1.0 | kcal/mol | IMRE | Larson and McMahon, 1984 | gas phase; B,B,M |
| ΔrG° | 6.50 | kcal/mol | TDEq | French, Ikuta, et al., 1982 | gas phase; B |
Free energy of reaction
| ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 6.6 | 300. | PHPMS | Paul and Kebarle, 1991 | gas phase; from Ph. D. thesis of S. Chowdhury, Entropy change calculated or estimated; M |
| 6.5 | 300. | PHPMS | French, Ikuta, et al., 1982 | gas phase; M |
C6H4Cl- + =
By formula: C6H4Cl- + H+ = C6H5Cl
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 391.0 ± 1.9 | kcal/mol | Bran | Wenthold and Squires, 1995 | gas phase; B |
| ΔrH° | 390.2 ± 2.1 | kcal/mol | G+TS | Wenthold and Squires, 1994 | gas phase; between furan, pyridine; B |
| ΔrH° | 390.2 ± 2.1 | kcal/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 |
| ΔrG° | 382.8 ± 2.0 | kcal/mol | H-TS | Wenthold and Squires, 1995 | gas phase; B |
| ΔrG° | 382.0 ± 2.0 | kcal/mol | IMRB | Wenthold and Squires, 1994 | gas phase; between furan, pyridine; B |
| ΔrG° | 382.0 ± 2.0 | kcal/mol | IMRB | Wenthold, Paulino, et al., 1991 | gas phase; Between H2O, furan. Wenthold and Squires, 1994 indicates isomerization occuring.; B |
C6H4Cl- + =
By formula: C6H4Cl- + H+ = C6H5Cl
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 394.4 ± 1.3 | kcal/mol | Bran | Wenthold and Squires, 1995 | gas phase; B |
| ΔrH° | 389.7 ± 2.1 | kcal/mol | G+TS | Wenthold and Squires, 1994 | gas phase; between furan, pyridine; B |
| ΔrH° | 389.7 ± 2.1 | kcal/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 |
| ΔrG° | 386.6 ± 1.4 | kcal/mol | H-TS | Wenthold and Squires, 1995 | gas phase; B |
| ΔrG° | 382.0 ± 2.0 | kcal/mol | IMRB | Wenthold and Squires, 1994 | gas phase; between furan, pyridine; B |
| ΔrG° | 382.0 ± 2.0 | kcal/mol | IMRB | Wenthold, Paulino, et al., 1991 | gas phase; Between H2O, furan. Wenthold and Squires, 1994 indicates isomerization occuring.; B |
C6H4Cl- + =
By formula: C6H4Cl- + H+ = C6H5Cl
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 386.7 ± 2.1 | kcal/mol | G+TS | Andrade and Riveros, 1996 | gas phase; B |
| ΔrH° | 388.2 ± 2.0 | kcal/mol | Bran | Wenthold and Squires, 1995 | gas phase; B |
| ΔrH° | 387.7 ± 3.1 | kcal/mol | G+TS | Wenthold, Paulino, et al., 1991 | gas phase; Between PhF, furan; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 378.5 ± 2.0 | kcal/mol | IMRE | Andrade and Riveros, 1996 | gas phase; B |
| ΔrG° | 380.0 ± 2.1 | kcal/mol | H-TS | Wenthold and Squires, 1995 | gas phase; B |
| ΔrG° | 379.5 ± 3.0 | kcal/mol | IMRB | Wenthold, Paulino, et al., 1991 | gas phase; Between PhF, furan; B |
| ΔrG° | 379.0 ± 5.0 | kcal/mol | IMRB | Bartmess and McIver Jr., 1979 | gas phase; Between H2O, MeOH; B |
+
= (
•
)
By formula: Br- + C6H5Cl = (Br- • C6H5Cl)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 11.1 ± 1.8 | kcal/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 |
| ΔrS° | 20. | cal/mol*K | N/A | Paul and Kebarle, 1991 | gas phase; Entropy change calculated or estimated; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 2.6 ± 1.0 | kcal/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
| ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 2.6 | 423. | PHPMS | Paul and Kebarle, 1991 | gas phase; Entropy change calculated or estimated; M |
By formula: C6H7N+ + C6H5Cl = (C6H7N+ • C6H5Cl)
Bond type: Charge transfer bond (positive ion)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 11.7 | kcal/mol | PHPMS | Meot-Ner (Mautner) and El-Shall, 1986 | gas phase; Entropy change calculated or estimated; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 26. | cal/mol*K | N/A | Meot-Ner (Mautner) and El-Shall, 1986 | gas phase; Entropy change calculated or estimated; M |
Free energy of reaction
| ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 4.0 | 297. | PHPMS | Meot-Ner (Mautner) and El-Shall, 1986 | gas phase; Entropy change calculated or estimated; M |
By formula: C9H12+ + C6H5Cl = (C9H12+ • C6H5Cl)
Bond type: Charge transfer bond (positive ion)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 11.4 | kcal/mol | PHPMS | Meot-Ner (Mautner), Hamlet, et al., 1978 | gas phase; Entropy change calculated or estimated; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 27. | cal/mol*K | N/A | Meot-Ner (Mautner), Hamlet, et al., 1978 | gas phase; Entropy change calculated or estimated; M |
Free energy of reaction
| ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 2.9 | 300. | PHPMS | Meot-Ner (Mautner), Hamlet, et al., 1978 | gas phase; Entropy change calculated or estimated; M |
+
= (
•
)
By formula: NO- + C6H5Cl = (NO- • C6H5Cl)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 38.5 | kcal/mol | ICR | Reents and Freiser, 1981 | gas phase; switching reaction,Thermochemical ladder(NO+)C2H5OH, Entropy change calculated or estimated; Farid and McMahon, 1978; M |
+
=
+
By formula: C6H5Cl + C12H17Cl = C9H11Cl + C9H11Cl
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -0.20 ± 0.10 | kcal/mol | Eqk | Nesterova, Rozhnov, et al., 1985 | liquid phase; ALS |
+
=
+
By formula: C6H5Cl + C14H21Cl = C10H13Cl + C10H13Cl
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -0.06 ± 0.17 | kcal/mol | Eqk | Kovzel, Nesterova, et al., 1981 | liquid phase; ALS |
+
=
+
By formula: C9H11Cl + C6H6 = C6H5Cl + C9H12
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -0.14 ± 0.10 | kcal/mol | Eqk | Nesterova, Rozhnov, et al., 1985 | liquid phase; ALS |
+
= 2
By formula: C6H5Cl + C14H21Cl = 2C10H13Cl
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 0. ± 0.02 | kcal/mol | Eqk | Kovzel, Nesterova, et al., 1981 | liquid phase; ALS |
+
=
+
By formula: C6H6 + Cl2 = C6H5Cl + HCl
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -32.0 | kcal/mol | Cm | Kirkbride, 1956 | liquid phase; ALS |
References
Go To: Top, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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 ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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