Gas-phase reactions of CH
5+, C
2H
5+, and C
3H
5+ ions with monohalogenated benzenes (PhX=F, Cl, Br, and I) were studied using an ion-trap type of GC/MS at a low chemical-ionization gas pressure of CH
4. The major product channel involves dissociative and non-dissociative proton transfer leading to [M+H-HX+CH
4]
+=[PhCH
3+H]
+ for PhF, [M+H]
+ for PhCl and PhBr, and [M+H-X]
+=PhH
+ for PhI. Adduct ions and their decomposition products are also found in reactions of C
2H
5+ and C
3H
5+. The reaction mechanism is discussed based on the reaction-time dependence of product-ion distributions and semi-empirical calculations of the heat of reaction for each process.
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