Concepedia

Structure and Reactivity of a Highly Twisted Amide

Shinji Yamada

Angewandte Chemie International Edition in English · 1993 · 101 citations · 10 references

DOI

Concepts

Abstract

The largest twist angle of 74.3° at a C(O)N bond known so far was detected in the amide 1 by IR, UV, and NMR spectroscopy, as well as X-ray crystallography. In 1 the thiazolidine ring is almost perpendicular to the CO group, which makes this compound extremely reactive.

References

10

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Distorted amides as models for activated peptide N-C:O units produced during enzyme-catalyzed acyl transfer reactions. 1. The mechanism of hydrolysis of 3,4-dihydro-2-oxo-1,4-ethanoquinoline and 2,3,4,5-tetrahydro-2-oxo-1,5-ethanobenzazepine

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Toshio Izawa, Teruaki Mukaiyama · Bulletin of the Chemical Society of Japan · 1979 · 57 citations · Full text

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Shinji Yamada · The Journal of Organic Chemistry · 1992 · 45 citations

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