Using dipoles to control the directionality of functional groups: Syn- and anti-oriented benzene-1,3-dicarboxamides

Mark S. Betson*, Jonathan Clayden, Ho Kam Lam, Madeleine Helliwell

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

20 Citations (Scopus)

Abstract

Poles apart: The relative orientation of a pair of functional groups-amides in this case-can be controlled by the choice of the substituent that lies between them. Groups which are effectively cylindrically symmetrical (Me, Cl) allow direct interaction between the dipoles of the amides and induce an anti orientation, whereas polar groups (OCOR, OSO2R, SO2R) interact with the dipole of both amides to yield a syn orientation (see picture).

Original languageEnglish
Pages (from-to)1241-1244
Number of pages4
JournalAngewandte Chemie - International Edition
Volume44
Issue number8
Early online date14 Jan 2005
DOIs
Publication statusPublished - 11 Feb 2005

Keywords

  • Amides
  • Conformation analysis
  • Dipoles
  • Electrostatic interactions

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