Specific substituent effects in the dehalogenation of halobenzene derivatives by the gaseous Broensted acid CH5+ was written by Leung, Hei-Wun;Harrison, Alex G.. And the article was included in Journal of the American Chemical Society in 1980.Synthetic Route of C8H10ClN This article mentions the following:
In the methane chem. ionization mass spectra of chlorobenzene derivatives containing an electron-donating substituent meta to the chlorine, the protonated mol. ions, MH+, formed in the initial protonation reaction undergo extensive loss of HCl to form substituted Ph cations. This dehalogenation reaction is not observed when the substituent is ortho or para to the chlorine (except for the p-dimethylamino substituent) nor for electron-withdrawing substituents. For fluorobenzene derivatives loss of HF from MH+ is observed when the substituent is meta or para to the fluorine but not when it is ortho to the fluorine. The origin of these unusual substituent effects is discussed and it is concluded that the substituents act to alter the carbon-halogen bond dipole. This bond dipole in turn exerts a kinetic effect which either alters the activation energy for elimination of the neutral hydrogen halide from MH+ or, more likely, influences the extent of protonation at the halogen through localized ion-bond dipole interactions in the collision complex. In the experiment, the researchers used many compounds, for example, 2-Chloro-N,N-dimethylaniline (cas: 698-01-1Synthetic Route of C8H10ClN).
2-Chloro-N,N-dimethylaniline (cas: 698-01-1) belongs to organic chlorides. An organic chloride is an organic compound containing at least one covalently bonded atom of chlorine. Their wide structural variety and divergent chemical properties lead to a broad range of names and applications. Alkyl chlorides readily react with amines to give substituted amines. Alkyl chlorides are substituted by softer halides such as the iodide in the Finkelstein reaction.Synthetic Route of C8H10ClN
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics