• Home
  1. Home
  2. The optical resolution of bicyclo[2.2.1]Hept-5-Ene-2-cyanohydrins using brucine : a crystallographic and molecular-mechanics study
Scientific article
English

The optical resolution of bicyclo[2.2.1]Hept-5-Ene-2-cyanohydrins using brucine : a crystallographic and molecular-mechanics study

Contributors

Pinkerton, A. A.; Carrupt, Pierre-Alain; Claret, F.; Vogel, Pierre

Published in

Acta crystallographica. Section C, Crystal structure communications, vol. 49, p. 1632-1636

Publication date

1993

Abstract

The structures of the brucine complexes with (+)-(1R,2S,4R)-bicyclo[2.2.1]hept-5-ene-2-cyanohydrin and (+)-(1R,2R,4R)-7-oxabicyclo[2.2.1]hept-5-ene-2-cyanohydrin {(6) 2,3-dimethoxystrychnidine-2-hydroxybicyc-lo[2.2.1]hept-5-ene-2-carbonitr ile (1/1) and (7) 2,3-dime-thoxystrychnidine-2-hydroxy-7-oxabicyclo[2.2. I]hept-5-ene-2-carbonitrile (1/1)} have been determined. The primary interaction in the complexes is a hydrogen bond between the OH group of the cyanohydrin and the most basic N atom of brucine. Molecular-mechanics calculations on the 7-oxa derivative indicate that the enantiomeric cyanohydrin will fit into the same cavity in the brucine matrix at the cost of ca 71 kJ mol-1

UNIGE affiliation entities

Not a UNIGE publication

Citation (ISO format)

PINKERTON, A. A. et al. The optical resolution of bicyclo[2.2.1]Hept-5-Ene-2-cyanohydrins using brucine : a crystallographic and molecular-mechanics study. In: Acta crystallographica. Section C, Crystal structure communications, 1993, vol. 49, p. 1632–1636.

Identifiers

  • PID : unige:9959

Journal ISSN

0108-2701
589views
0downloads

Technical informations

Creation

06/08/2010 10:46:50

First validation

06/08/2010 10:46:50

Update

14/03/2023 15:56:28

Status update

14/03/2023 15:56:28

Last indexation

29/10/2024 16:21:10
All rights reserved by Archive ouverte UNIGE and the University of Geneva
OpenAIRE Indexed & Validated