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Benzene, 1-chloro-4-methyl-

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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
Deltacliquid-3750. ± 10.kJ/molCcbSmith, Bjellerup, et al., 1953At 291 °K

Phase change 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:
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
Tboil435. ± 1.KAVGN/AAverage of 13 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus280.5 ± 0.6KAVGN/AAverage of 9 values; Individual data points
Quantity Value Units Method Reference Comment
Tc615.90KN/ASimon, 1957Uncertainty assigned by TRC = 0.5 K; TRC
Quantity Value Units Method Reference Comment
Deltavap46.0kJ/molN/ABoublik, Fried, et al., 1984Based on data from 340. - 430. K. See also Basarová and Svoboda, 1991.; AC
Deltavap38.7 ± 0.02kJ/molVMathews, 1926ALS

Reduced pressure boiling point

Tboil (K) Pressure (bar) Reference Comment
317.20.013Weast and Grasselli, 1989BS

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
41.8375.N/ADykyj, Svoboda, et al., 1999Based on data from 362. - 435. K.; AC
41.7319.AStephenson and Malanowski, 1987Based on data from 304. - 436. K.; AC
43.5353.N/ABoublik, Fried, et al., 1984Based on data from 338. - 433. K.; AC
44.1293.N/AStull, 1947Based on data from 279. - 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 - 435.54.474581795.293-34.28Stull, 1947Coefficents calculated by NIST from author's data.

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Reference Comment
13.55280.7van Miltenburg, Alvarez-Larena, et al., 1996AC

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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- + Hydrogen cation = Benzene, 1-chloro-4-methyl-

By formula: C7H6Cl- + H+ = C7H7Cl

Quantity Value Units Method Reference Comment
Deltar1565. ± 8.8kJ/molG+TSCaldwell and Bartmessgas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar1535. ± 8.4kJ/molIMRECaldwell and Bartmessgas phase; value altered from reference due to change in acidity scale; B

Benzene, 1-chloro-4-methyl- + 1-Chloro-2,5-diisopropyl-4-methylbenzene = 1-Chloro-2-isopropyl-4-methylbenzene + 1-Chloro-3-isopropyl-4-methylbenzene

By formula: C7H7Cl + C13H19Cl = C10H13Cl + C10H13Cl

Quantity Value Units Method Reference Comment
Deltar-0.72 ± 0.50kJ/molEqkNesterova, Rozhnov, et al., 1985liquid phase; ALS

Gas phase ion energetics 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 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 ± 0.03eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)762.9kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity735.2kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.8 ± 0.1EITajima and Tsuchiya, 1972LLK
8.70 ± 0.02PIWatanabe, Nakayama, et al., 1962RDSH
8.69 ± 0.02PIWatanabe, 1957RDSH
8.80PEDomnin, Lakshin, et al., 1985Vertical value; LBLHLM

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C5H5+15.7 ± 0.2C2H2+ClEITajima and Tsuchiya, 1973LLK
C5H5+15.66 ± 0.15C2H2EITajima and Tsuchiya, 1972LLK
C7H6Cl+12.11 ± 0.15HEISelim, Rabbih, et al., 1994LL
C7H7+11.12 ± 0.06ClEISelim, Rabbih, et al., 1994LL
C7H7+11.5 ± 0.3ClEIMcLafferty and Winkler, 1974LLK
C7H7+11.4 ± 0.1ClEITajima and Tsuchiya, 1972LLK
C7H7+11.7ClEIYeo and Williams, 1970RDSH
C7H7+11.1 ± 0.1ClEIBrown, 1970RDSH

De-protonation reactions

C7H6Cl- + Hydrogen cation = Benzene, 1-chloro-4-methyl-

By formula: C7H6Cl- + H+ = C7H7Cl

Quantity Value Units Method Reference Comment
Deltar1565. ± 8.8kJ/molG+TSCaldwell and Bartmessgas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar1535. ± 8.4kJ/molIMRECaldwell and Bartmessgas phase; value altered from reference due to change in acidity scale; B

IR Spectrum

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), References, Notes

Data compiled by: Coblentz Society, Inc.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director


Mass spectrum (electron ionization)

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Mass spectrum
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Additional Data

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin NIST Mass Spectrometry Data Center, 1990.
NIST MS number 114651

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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]

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]

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, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), References