Benzene, 1-(chloromethyl)-4-methyl-
- Formula: C8H9Cl
- Molecular weight: 140.610
- IUPAC Standard InChIKey: DMHZDOTYAVHSEH-UHFFFAOYSA-N
- CAS Registry Number: 104-82-5
- 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. - Isotopologues:
- Other names: p-Xylene, α-chloro-; α-Chloro-p-xylene; p-Chloromethyltoluene; p-Methylbenzyl chloride; p-Xylyl chloride; p-Xylyl-α-chloride; 1-(Chloromethyl)-4-methylbenzene; 4-Methylbenzyl chloride; 1-Methyl-4-(chloromethyl)benzene; 4-(Chloromethyl)toluene; p-Xylene, alpha-chloro-; (4-Methylphenyl)methyl chloride; NSC 46590; p-Tolylmethyl chloride
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Gas phase ion energetics data
Go To: Top, Mass spectrum (electron ionization), Gas Chromatography, 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
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.79 ± 0.03 | PI | Ponomarev, Takhimova, et al., 1974 | LLK |
De-protonation reactions
C8H8Cl- + =
By formula: C8H8Cl- + H+ = C8H9Cl
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 375.1 ± 2.3 | kcal/mol | D-EA | Hammad and Wenthold, 2000 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 367.9 ± 2.4 | kcal/mol | H-TS | Hammad and Wenthold, 2000 | gas phase; B |
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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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. |
---|---|
NIST MS number | 3727 |
Gas Chromatography
Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), 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
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | SE-54 | 115. | 1136. | Bermejo, Blanco, et al., 1986 | N2; Column length: 25. m; Column diameter: 0.22 mm |
Capillary | Squalane | 115. | 1080. | Bermejo, Blanco, et al., 1986 | N2; Column length: 45. m; Column diameter: 0.5 mm |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | OV-1 | 1094.0 | Gautzsch and Zinn, 1996 | 8. K/min; Tstart: 35. C; Tend: 300. C |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | OV-101 | 1088. | Zenkevich and Makarov, 2007 | N2, 6. K/min; Column length: 25. m; Column diameter: 0.2 mm; Tstart: 60. C; Tend: 240. C |
Capillary | OV-101 | 1096. | Zenkevich and Makarov, 2007 | N2, 6. K/min; Column length: 25. m; Column diameter: 0.2 mm; Tstart: 60. C; Tend: 240. C |
Capillary | OV-101 | 1098. | Zenkevich, 2001 | N2, 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
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Methyl Silicone | 1084. | Zenkevich, 1999 | Program: not specified |
References
Go To: Top, Gas phase ion energetics data, 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.
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]
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]
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
Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
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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