X-Ray and SCF–MO model study of the complex formed between N-bromosuccinimide and 1,4-diazabicyclo[2.2.2]octane

Abstract

X-Ray analysis of the structure of the complex (1) formed between N-bromosuccinimide and the tertiary base 1,4-diazabicyclo[2.2.2]octane(DABCO)shows the compound to contain a nearly linear [175.1(2)°]N–Br–N bond with an exceptionally long bromine to DABCO distance [2.332(4)Å]and a bromine to succinimido distance of 1.945(4)Å; MNDO and ab initio SCF-MO calculations on the model system N-chlorosuccinimide + NH₃show charge transfer to occur from both the halogen and the amine to the succinimido moiety upon complex formation.