Benzene, 1-chloro-4-methyl-
- Formula: C7H7Cl
- Molecular weight: 126.583
- IUPAC Standard InChIKey: NPDACUSDTOMAMK-UHFFFAOYSA-N
- CAS Registry Number: 106-43-4
- Chemical structure:
This structure is also available as a 2d Mol file - Other names: Toluene, p-chloro-; p-Chlorotoluene; p-Tolyl chloride; 1-Chloro-4-methylbenzene; 4-Chloro-1-methylbenzene; 4-Chlorotoluene; para-Chlorotoluene; 1-Methyl-4-chlorobenzene; 4-Tolyl chloride; 4-Methylphenyl chloride; NSC 404114
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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔcH°liquid | -3750. ± 10. | kJ/mol | Ccb | Smith, Bjellerup, et al., 1953 | At 291 °K |
Reaction 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:
B - John E. Bartmess
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
C7H6Cl- + =
By formula: C7H6Cl- + H+ = C7H7Cl
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1565. ± 8.8 | kJ/mol | G+TS | Caldwell and Bartmess | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1535. ± 8.4 | kJ/mol | IMRE | Caldwell and Bartmess | gas phase; value altered from reference due to change in acidity scale; B |
By formula: C7H7Cl + C13H19Cl = C10H13Cl + C10H13Cl
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -0.72 ± 0.50 | kJ/mol | Eqk | Nesterova, Rozhnov, et al., 1985 | liquid phase; ALS |
Gas phase ion energetics 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
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
LL - Sharon G. Lias and Joel F. Liebman
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 8.69 ± 0.03 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 762.9 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 735.2 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.8 ± 0.1 | EI | Tajima and Tsuchiya, 1972 | LLK |
8.70 ± 0.02 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
8.69 ± 0.02 | PI | Watanabe, 1957 | RDSH |
8.80 | PE | Domnin, Lakshin, et al., 1985 | Vertical value; LBLHLM |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C5H5+ | 15.7 ± 0.2 | C2H2+Cl | EI | Tajima and Tsuchiya, 1973 | LLK |
C5H5+ | 15.66 ± 0.15 | C2H2 | EI | Tajima and Tsuchiya, 1972 | LLK |
C7H6Cl+ | 12.11 ± 0.15 | H | EI | Selim, Rabbih, et al., 1994 | LL |
C7H7+ | 11.12 ± 0.06 | Cl | EI | Selim, Rabbih, et al., 1994 | LL |
C7H7+ | 11.5 ± 0.3 | Cl | EI | McLafferty and Winkler, 1974 | LLK |
C7H7+ | 11.4 ± 0.1 | Cl | EI | Tajima and Tsuchiya, 1972 | LLK |
C7H7+ | 11.7 | Cl | EI | Yeo and Williams, 1970 | RDSH |
C7H7+ | 11.1 ± 0.1 | Cl | EI | Brown, 1970 | RDSH |
De-protonation reactions
C7H6Cl- + =
By formula: C7H6Cl- + H+ = C7H7Cl
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1565. ± 8.8 | kJ/mol | G+TS | Caldwell and Bartmess | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1535. ± 8.4 | kJ/mol | IMRE | Caldwell and Bartmess | gas phase; value altered from reference due to change in acidity scale; B |
References
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
Caldwell and Bartmess
Caldwell, G.; Bartmess, J.E.,
, Unpublished results. [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]
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [all data]
Tajima and Tsuchiya, 1972
Tajima, S.; Tsuchiya, T.,
The effects of the repeller voltage and the shield voltage on appearance potential measurements by electron impact,
Shitsuryo Bunseki, 1972, 20, 117. [all data]
Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J.,
Ionization potentials of some molecules,
J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]
Watanabe, 1957
Watanabe, K.,
Ionization potentials of some molecules,
J. Chem. Phys., 1957, 26, 542. [all data]
Domnin, Lakshin, et al., 1985
Domnin, I.N.; Lakshin, A.M.; Misharev, A.D.; Orlov, V.M.; Takhistov, V.V.,
Thermochemical investigation of some hydrocarbon ions generated by photoionization,
J. Org. Chem. USSR, 1985, 21, 1149. [all data]
Tajima and Tsuchiya, 1973
Tajima, S.; Tsuchiya, T.,
Energetics consideration of C5H5+ ions produced from various precursors by electron impact,
Bull. Chem. Soc. Jpn., 1973, 46, 3291. [all data]
Selim, Rabbih, et al., 1994
Selim, E.T.M.; Rabbih, M.A.; Fahmey, M.A.; Hawash, M.F.,
Loss of H and Cl from the molecular ions of chlorotoluene isomers using electron impact mass spectrometry,
Int. J. Mass Spectrom. Ion Processes, 1994, 134, 119. [all data]
McLafferty and Winkler, 1974
McLafferty, F.W.; Winkler, J.,
Gaseous tropylium, benzyl, tolyl, and norbornadienyl cations,
J. Am. Chem. Soc., 1974, 96, 5182. [all data]
Yeo and Williams, 1970
Yeo, A.N.H.; Williams, D.H.,
Rearrangement in the molecular ions of halogenotoluenes prior to fragmentation in the mass spectrometer,
Chem. Commun., 1970, 886. [all data]
Brown, 1970
Brown, P.,
Kinetic studies in mass spectrometry-IV. The [M - Cl] reaction in substituted chlorobenzenes and the question of molecular ion isomerization,
Org. Mass Spectrom., 1970, 3, 639. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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