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Literature DB >> 29711382

The Most Twisted Amide: Structure and Reactions.

Anthony J Kirby¹, Igor V Komarov¹, Peter D Wothers¹, Neil Feeder¹.

Abstract

The title amide 1 behaves more like a ketone-up to a point! The crystal structure of this (90°) twisted amide shows a pyramidal nitrogen atom next to a planar carbonyl group. © 1998 WILEY-VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany.

Entities: Chemical

Keywords: Amides; Cage compounds; Ketones; Stereoelectronic effects

Year: 1998 PMID： 29711382 DOI： 10.1002/(SICI)1521-3773(19980403)37:6<785::AID-ANIE785>3.0.CO;2-J

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

Keyword Cloud
Cited

13 in total

1. Electrospray ionization (ESI) fragmentations and dimethyldioxirane reactivities of three diverse lactams having full, half, and zero resonance energies.

Authors: Kathleen M Morgan; David J Ashline; Jessica P Morgan; Arthur Greenberg
Journal: J Org Chem Date: 2013-12-30 Impact factor: 4.354

2. Generation of aza-ortho-xylylenes via ring opening of 2-(2-acylaminophenyl)aziridines: application in the construction of the communesin ring system.

Authors: Seth L Crawley; Raymond L Funk
Journal: Org Lett Date: 2006-08-31 Impact factor: 6.005

3. Structure and Reactivity of Highly Twisted N-Acylimidazoles.

Authors: Elizabeth A Stone; Brandon Q Mercado; Scott J Miller
Journal: Org Lett Date: 2019-03-12 Impact factor: 6.005

4. Structures of the Most Twisted Thioamide and Selenoamide: Effect of Higher Chalcogens of Twisted Amides on N-C(X) Resonance.

Authors: Qun Zhao; Guangchen Li; Pradeep Nareddy; Frank Jordan; Roger Lalancette; Roman Szostak; Michal Szostak
Journal: Angew Chem Int Ed Engl Date: 2022-07-26 Impact factor: 16.823

Review 5. Acyclic Twisted Amides.

Authors: Guangrong Meng; Jin Zhang; Michal Szostak
Journal: Chem Rev Date: 2021-08-18 Impact factor: 72.087

The Most Twisted Amide: Structure and Reactions.

1. Electrospray ionization (ESI) fragmentations and dimethyldioxirane reactivities of three diverse lactams having full, half, and zero resonance energies.

2. Generation of aza-ortho-xylylenes via ring opening of 2-(2-acylaminophenyl)aziridines: application in the construction of the communesin ring system.

3. Structure and Reactivity of Highly Twisted N-Acylimidazoles.

4. Structures of the Most Twisted Thioamide and Selenoamide: Effect of Higher Chalcogens of Twisted Amides on N-C(X) Resonance.

Review 5. Acyclic Twisted Amides.

6. Pyramidalization/twisting of the amide functional group via remote steric congestion triggered by metal coordination.

Review 7. Amide Bond Activation of Biological Molecules.

8. Amide Activation in Ground and Excited States.

9. Modular Access to Substituted Azocanes via a Rhodium-Catalyzed Cycloaddition-Fragmentation Strategy.

Review 10. Heteroatom Substitution at Amide Nitrogen-Resonance Reduction and HERON Reactions of Anomeric Amides.