Benzene, 1-(chloromethyl)-4-methyl-
- Formula: C8H9Cl
- Molecular weight: 140.610
- IUPAC Standard InChI: InChI=1S/C8H9Cl/c1-7-2-4-8(6-9)5-3-7/h2-5H,6H2,1H3
- 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
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- 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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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
AC - William E. Acree, Jr., James S. Chickos
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tboil | 474.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Enthalpy of vaporization
| ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 44.9 | 391. | A | Stephenson and Malanowski, 1987 | Based on data from 376. to 457. K. See also Dykyj, Svoboda, et al., 1999.; 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 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° | 1569. ± 9.6 | kJ/mol | D-EA | Hammad and Wenthold, 2000 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1539. ± 10. | kJ/mol | H-TS | Hammad and Wenthold, 2000 | gas phase; 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.
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]
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]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
Tboil Boiling point ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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