Effect of the complex-forming characteristics of aromatic solvents on the selectivity of free-radical chlorination. Chlorination of 2-chloropropane
During investigation of the effect of six solvents of aromatic nature on the selectivity of the free-radical chlorination of 2-chloropropane it was found that the (CH/sub 3/CCl/sub 2/CH/sub 3/)/(CH/sub 3/CHClCH/sub 2/Cl) ratio increases with increase in the content of the solvent in the reaction mixture and with decrease in the temperature. The obtained data were interpreted by a mechanism involving the formation of ..pi.. complexes between the chlorine atoms and the aromatic molecules ArH ..-->.. Cl/sup dot/ as particles responsible for the selective effect of the solvents. On the basis of the adopted mechanism an equation was obtained for the selectivity of the process with parameters reflecting the relative reactivities of the various C-H bonds in the 2-chloropropane during their reaction with the chlorine atoms and the ArH ..-->.. Cl/sup dot/ complexes. The differences in the activation energies of the competing reactions of the C-H bonds with ArH ..-->.. Cl/sup dot/ correlate with the electron-donating characteristics of the solvent molecules.
- Research Organization:
- D. I. Mendeleev Moscow Chemical Technology Institute (USSR)
- OSTI ID:
- 7160053
- Journal Information:
- J. Org. Chem. USSR (Engl. Transl.); (United States), Vol. 23:6; Other Information: Translated from Zh. Org. Khim.; 23: No. 6, 1238-1244(Jun 1987)
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
CHLORINATED ALIPHATIC HYDROCARBONS
CHLORINATION
ORGANIC SOLVENTS
ACTIVATION ENERGY
COMPLEXOMETRY
BENZENE
BINDING ENERGY
CHLORINATED AROMATIC HYDROCARBONS
ELECTRON DENSITY
ELECTRONS
FLUORINATED AROMATIC HYDROCARBONS
HYDROGEN TRANSFER
NITRILES
PROPANE
QUANTITY RATIO
SOLVENT PROPERTIES
TEMPERATURE DEPENDENCE
THIN-LAYER CHROMATOGRAPHY
VALENCE
ALKANES
AROMATICS
CHEMICAL REACTIONS
CHROMATOGRAPHY
ELEMENTARY PARTICLES
ENERGY
FERMIONS
HALOGENATED ALIPHATIC HYDROCARBONS
HALOGENATED AROMATIC HYDROCARBONS
HALOGENATION
HYDROCARBONS
LEPTONS
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC FLUORINE COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
SEPARATION PROCESSES
SOLVENTS
400201* - Chemical & Physicochemical Properties