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

doi:10.1039/C39840000276

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

DQ - Departamento de Química

Research output: Contribution to journal › Article › peer-review

28 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 language	English
Pages (from-to)	276-278
Number of pages	3
Journal	Journal of the Chemical Society, Chemical Communications
Issue number	5
DOIs	https://doi.org/10.1039/C39840000276
Publication status	Published - 1 Jan 1984

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title = "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) {\AA}] and a bromine to succinimido distance of 1.945(4) {\AA}; 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.",

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T1 - X-ray and SCF-MO model study of the complex formed between N-bromosuccinimide and 1,4-Diazabicyclo[2.2.2]octane

AU - Crowston, Edward H.

AU - Lobo, Ana M.

AU - Prabhakar, Sundaresan

AU - Rzepa, Henry S.

AU - Williams, David J.

PY - 1984/1/1

Y1 - 1984/1/1

N2 - 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.

AB - 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.

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

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