22118-09-8

Clear yellow liquid

Bromoacetyl chloride photodissociation has been interpreted as a typical process in which nonadiabatic effects play a dominant role. Stationary points (minima and saddle points) and minimum energy paths are characterized on the S0 and S1 potential energy surfaces. The five adiabatic excited electronic states are converted to a nonadiabatic representation using a quadruple-path nonadiabatic approach. The nonadiabatic potential energy matrix of the first five excited singlet states is constructed along several cuts of the potential energy hypersurface. The thermochemical properties of the photodissociation reaction and the comparison with experimental translational energy profiles strongly suggest that nonadiabatic effects dominate the C-Br cleavage, but the reaction proceeds along an energetically allowed nonadiabatic path to excited state products rather than being nonadiabatically inhibited. This conclusion is also supported by the low values of nonadiabatic coupling along the C-Br cleavage reaction path^[1].

Bromoacetyl chloride was used in the synthesis of α,α-disubstituted thioisomünchnones. It was also used in the preparation of 1,3-dibromoacetone.

[1] ROSENDO VALERO; Donald G T. Nonadiabatic effects in C-Br bond scission in the photodissociation of bromoacetyl chloride.[J]. Journal of Chemical Physics, 2006, 125 19: 194305. DOI:10.1063/1.2363991.