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Issue 18, 2016
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The salts of chloronium ions R–Cl+–R (R = CH3 or CH2Cl): formation, thermal stability, and interaction with chloromethanes

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Abstract

The interaction of CH3Cl/CD3Cl or CH2Cl2/CD2Cl2 with the carborane acid H(CHB11Cl11) (abbreviated as H{Cl11}) generates the salts of CH3–{Cl11} and CH2Cl–{Cl11} and their deuterio analogs, respectively, which are analogs of the salts of asymmetric chloronium cations. Next, salts of chloronium cations CH3–Cl+–CH3, ClCH2–Cl+–CH2Cl, and ClCH2–Cl+–CH3 and their deuterio analogs were obtained from the above compounds. The asymmetric ClCH2–Cl+–CH3 cation was found to be unstable, and at ambient temperature, slowly disproportionated into symmetric cations (CH3)2Cl+ and (CH2Cl)2Cl+. At a high temperature (150 °C), disproportionation was completed within 5 minutes, and the resulting cations further decomposed into CH3–{Cl11} and CH2Cl–{Cl11}. The molecular fragment ClCH2–(X) of the compounds (X = {Cl11}, –Cl+–CH2Cl, or –Cl+–CH3) is involved in exchange reactions with CH2Cl2 and CHCl3, converting into CH3–(X) with the formation of chloroform and CCl4, respectively.

Graphical abstract: The salts of chloronium ions R–Cl+–R (R = CH3 or CH2Cl): formation, thermal stability, and interaction with chloromethanes

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Supplementary files

Article information


Submitted
11 Feb 2016
Accepted
04 Apr 2016
First published
07 Apr 2016

This article is Open Access

Phys. Chem. Chem. Phys., 2016,18, 12896-12904
Article type
Paper
Author version available

The salts of chloronium ions R–Cl+–R (R = CH3 or CH2Cl): formation, thermal stability, and interaction with chloromethanes

E. S. Stoyanov, Phys. Chem. Chem. Phys., 2016, 18, 12896
DOI: 10.1039/C6CP00946H

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