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

Edward H. Crowston, Ana M. Lobo, Sundaresan Prabhakar, Henry S. Rzepa, David J. Williams

Research output: Contribution to journalArticle

26 Citations (Scopus)

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 + NH3 show charge transfer to occur from both the halogen and the amine to the succinimido moiety upon complex formation.

Original languageEnglish
Pages (from-to)276-278
Number of pages3
JournalJournal of the Chemical Society, Chemical Communications
Issue number5
DOIs
Publication statusPublished - 1 Jan 1984

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