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Benzene, 1-(chloromethyl)-4-methyl-


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
AC - William E. Acree, Jr., James S. Chickos

Quantity Value Units Method Reference Comment
Tboil474.2KN/AWeast and Grasselli, 1989BS

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
44.9391.AStephenson and Malanowski, 1987Based on data from 376. - 457. K. See also Dykyj, Svoboda, et al., 1999.; AC

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 by: John E. Bartmess

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

C8H8Cl- + Hydrogen cation = Benzene, 1-(chloromethyl)-4-methyl-

By formula: C8H8Cl- + H+ = C8H9Cl

Quantity Value Units Method Reference Comment
Deltar1569. ± 9.6kJ/molD-EAHammad and Wenthold, 2000gas phase
Quantity Value Units Method Reference Comment
Deltar1539. ± 10.kJ/molH-TSHammad and Wenthold, 2000gas phase

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 compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

IE (eV) Method Reference Comment
8.79 ± 0.03PIPonomarev, Takhimova, et al., 1974LLK

De-protonation reactions

C8H8Cl- + Hydrogen cation = Benzene, 1-(chloromethyl)-4-methyl-

By formula: C8H8Cl- + H+ = C8H9Cl

Quantity Value Units Method Reference Comment
Deltar1569. ± 9.6kJ/molD-EAHammad and Wenthold, 2000gas phase; B
Quantity Value Units Method Reference Comment
Deltar1539. ± 10.kJ/molH-TSHammad and Wenthold, 2000gas phase; B

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

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


Mass spectrum (electron ionization)

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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: 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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Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
NIST MS number 3727

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Gas Chromatography

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

Kovats' RI, non-polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
CapillarySE-54115.1136.Bermejo, Blanco, et al., 1986N2; Column length: 25. m; Column diameter: 0.22 mm
CapillarySqualane115.1080.Bermejo, Blanco, et al., 1986N2; Column length: 45. m; Column diameter: 0.5 mm

Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryOV-11094.0Gautzsch and Zinn, 19968. K/min; Tstart: 35. C; Tend: 300. C

Normal alkane RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryOV-1011088.Zenkevich and Makarov, 2007N2, 6. K/min; Column length: 25. m; Column diameter: 0.2 mm; Tstart: 60. C; Tend: 240. C
CapillaryOV-1011096.Zenkevich and Makarov, 2007N2, 6. K/min; Column length: 25. m; Column diameter: 0.2 mm; Tstart: 60. C; Tend: 240. C
CapillaryOV-1011098.Zenkevich, 2001N2, 4. K/min; Column length: 25. m; Column diameter: 0.20 mm; Tstart: 60. C; Tend: 240. C

Normal alkane RI, non-polar column, custom temperature program

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Column type Active phase I Reference Comment
CapillaryMethyl Silicone1084.Zenkevich, 1999Program: not specified

References

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

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

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]

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]

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]

Hammad and Wenthold, 2000
Hammad, L.A.; Wenthold, P.G., Synthesis, characterization, and reactivity of the m-xylylene anion in the gas phase. The enthalpy of formation of m-xylylene, J. Am. Chem. Soc., 2000, 122, 45, 11203-11211, https://doi.org/10.1021/ja002138n . [all data]

Ponomarev, Takhimova, et al., 1974
Ponomarev, D.A.; Takhimova, V.V.; Akopyan, M.E.; Sergeyev, Y.L., Effect of alkyl groups on the stability of cations in the absence of solvation effects, Zh. Org. Khim., 1974, 10, 403. [all data]

Bermejo, Blanco, et al., 1986
Bermejo, J.; Blanco, C.G.; Guillén, M.D., Gas chromatography of deuterated and protiated chloro derivatives of 1,4-dimethylbenzene, J. Chromatogr., 1986, 351, 425-432, https://doi.org/10.1016/S0021-9673(01)83520-2 . [all data]

Gautzsch and Zinn, 1996
Gautzsch, R.; Zinn, P., Use of incremental models to estimate the retention indexes of aromatic compounds, Chromatographia, 1996, 43, 3/4, 163-176, https://doi.org/10.1007/BF02292946 . [all data]

Zenkevich and Makarov, 2007
Zenkevich, I.G.; Makarov, A.A., Identification of Alkylarene Chloromethylation Products Using Gas-Chromatographic Retention Indices, Russian Journal of General Chemistry, 2007, 77, 4, 611-619, https://doi.org/10.1134/S1070363207040196 . [all data]

Zenkevich, 2001
Zenkevich, I.G., Interpretation of Gas Chromatographic Retention Indices in estimation of Structures of Isomeric Products of Radical Chlorinating of Alkyl Arenes, Zh. Org. Khim., 2001, 37, 2, 283-293. [all data]

Zenkevich, 1999
Zenkevich, I.G., Mutual Correlation between Gas-Chromatographic Retention Indices of Organic Compounds from Different Series, Zh. Anal. Khim., 1999, 54, 12, 1272-1279. [all data]


Notes

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