Acyclic Twisted Amides

Chem Rev. 2021 Oct 27;121(20):12746-12783. doi: 10.1021/acs.chemrev.1c00225. Epub 2021 Aug 18.

Abstract

In this contribution, we provide a comprehensive overview of acyclic twisted amides, covering the literature since 1993 (the year of the first recognized report on acyclic twisted amides) through June 2020. The review focuses on classes of acyclic twisted amides and their key structural properties, such as amide bond twist and nitrogen pyramidalization, which are primarily responsible for disrupting nN to π*C═O conjugation. Through discussing acyclic twisted amides in comparison with the classic bridged lactams and conformationally restricted cyclic fused amides, the reader is provided with an overview of amidic distortion that results in novel conformational features of acyclic amides that can be exploited in various fields of chemistry ranging from organic synthesis and polymers to biochemistry and structural chemistry and the current position of acyclic twisted amides in modern chemistry.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Review

MeSH terms

  • Amides* / chemistry
  • Chemistry Techniques, Synthetic
  • Lactams* / chemistry
  • Molecular Conformation
  • Nitrogen / chemistry

Substances

  • Amides
  • Lactams
  • Nitrogen