4.8 Review

Acyclic Twisted Amides

期刊

CHEMICAL REVIEWS
卷 121, 期 20, 页码 12746-12783

出版社

AMER CHEMICAL SOC
DOI: 10.1021/acs.chemrev.1c00225

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资金

  1. Rutgers University
  2. NSF [CAREER CHE-1650766]
  3. NIH [1R35GM133326]
  4. China Scholarship Council [201808610096]
  5. Rutgers Graduate School

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This contribution provides a comprehensive overview of acyclic twisted amides since 1993, focusing on their key structural properties and applications in various fields of chemistry.
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 n(N) to pi*(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.

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