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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Phase change data
Go To: Top, Gas phase ion energetics 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 435. ± 1. | K | AVG | N/A | Average of 13 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 280.5 ± 0.6 | K | AVG | N/A | Average of 9 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 615.90 | K | N/A | Simon, 1957 | Uncertainty assigned by TRC = 0.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 46.0 | kJ/mol | N/A | Boublik, Fried, et al., 1984 | Based on data from 340. to 430. K. See also Basarová and Svoboda, 1991.; AC |
ΔvapH° | 38.7 ± 0.02 | kJ/mol | V | Mathews, 1926 | ALS |
Reduced pressure boiling point
Tboil (K) | Pressure (bar) | Reference | Comment |
---|---|---|---|
317.2 | 0.013 | Weast and Grasselli, 1989 | BS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
41.8 | 375. | N/A | Dykyj, Svoboda, et al., 1999 | Based on data from 362. to 435. K.; AC |
41.7 | 319. | A | Stephenson and Malanowski, 1987 | Based on data from 304. to 436. K.; AC |
43.5 | 353. | N/A | Boublik, Fried, et al., 1984 | Based on data from 338. to 433. K.; AC |
44.1 | 293. | N/A | Stull, 1947 | Based on data from 279. to 435. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
278.7 to 435.5 | 4.47458 | 1795.293 | -34.28 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
13.55 | 280.7 | van Miltenburg, Alvarez-Larena, et al., 1996 | AC |
Gas phase ion energetics data
Go To: Top, Phase change 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, Phase change 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.
Simon, 1957
Simon, M.,
Methods and Apparatus Used at the Bureau of Physicochemical Standards XV. Critical Constants and Straight-Line Diameters of Ten Hydrocarbons,
Bull. Soc. Chim. Belg., 1957, 66, 375-81. [all data]
Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E.,
The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]
Basarová and Svoboda, 1991
Basarová, Pavlína; Svoboda, Václav,
Calculation of heats of vaporization of halogenated hydrocarbons from saturated vapour pressure data,
Fluid Phase Equilibria, 1991, 68, 13-34, https://doi.org/10.1016/0378-3812(91)85008-I
. [all data]
Mathews, 1926
Mathews, J.H.,
The accurate measurement of heats of vaporization of liquids,
J. Am. Chem. Soc., 1926, 48, 562-576. [all data]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
Dykyj, Svoboda, et al., 1999
Dykyj, J.; Svoboda, J.; Wilhoit, R.C.; Frenkel, M.L.; Hall, K.R.,
Vapor Pressure of Chemicals: Part A. Vapor Pressure and Antoine Constants for Hydrocarbons and Sulfur, Selenium, Tellurium and Hydrogen Containing Organic Compounds, Springer, Berlin, 1999, 373. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Stull, 1947
Stull, Daniel R.,
Vapor Pressure of Pure Substances. Organic and Inorganic Compounds,
Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022
. [all data]
van Miltenburg, Alvarez-Larena, et al., 1996
van Miltenburg, J.C.; Alvarez-Larena, A.; Labrador, M.; Palacios, L.; Rodriguez-Romero, J.; Tauler, E.; Estop, E.,
The thermal properties of three (Cl-, Br-, I-) para-halotoluenes. Formation of glassy crystals,
Thermochimica Acta, 1996, 273, 31-42, https://doi.org/10.1016/0040-6031(95)02596-0
. [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]
Caldwell and Bartmess
Caldwell, G.; Bartmess, J.E.,
, Unpublished results. [all data]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point ΔfusH Enthalpy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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