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Updated: Jan 27, 2026

Magnetic Tweezers for the Measurement of Twist and Torque
Published on: May 19, 2014
Structure and Reactivity of Highly Twisted N-Acylimidazoles
Elizabeth A Stone1, Brandon Q Mercado1, Scott J Miller1
1Department of Chemistry , Yale University , 225 Prospect Street , New Haven , Connecticut 06520-8107 , United States.
Abstract:
A modular and efficient synthesis of highly twisted N-acylimidazoles is reported. These twist amides were characterized via X-ray crystallography, NMR spectroscopy, IR spectroscopy, and DFT calculations. Modification of the substituent proximal to the amide revealed a maximum torsional angle of 88.6° in the solid state, which may be the most twisted amide reported for a nonbicyclic system to date. Reactivity and stability studies indicate that these twisted N-acylimidazoles may be valuable, namely as acyl transfer reagents.
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