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), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 23:6; ISSN JOCYA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400201* -- Chemical & Physicochemical Properties
ACTIVATION ENERGY
ALKANES
AROMATICS
BENZENE
BINDING ENERGY
CHEMICAL REACTIONS
CHLORINATED ALIPHATIC HYDROCARBONS
CHLORINATED AROMATIC HYDROCARBONS
CHLORINATION
CHROMATOGRAPHY
COMPLEXOMETRY
ELECTRON DENSITY
ELECTRONS
ELEMENTARY PARTICLES
ENERGY
FERMIONS
FLUORINATED AROMATIC HYDROCARBONS
HALOGENATED ALIPHATIC HYDROCARBONS
HALOGENATED AROMATIC HYDROCARBONS
HALOGENATION
HYDROCARBONS
HYDROGEN TRANSFER
LEPTONS
NITRILES
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC FLUORINE COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC SOLVENTS
PROPANE
QUANTITY RATIO
SEPARATION PROCESSES
SOLVENT PROPERTIES
SOLVENTS
TEMPERATURE DEPENDENCE
THIN-LAYER CHROMATOGRAPHY
VALENCE