Dynamic and Persistent Cyclochirality in Hydrogen-Bonded Derivatives of Medium-Ring Triamines

• Published in: Journal of the American Chemical Society Vol. 145; no. 34; pp. 19030 - 19041
• Main Authors: Morris, David T. J., Wales, Steven M., Echavarren, Javier, Žabka, Matej, Marsico, Giulia, Ward, John W., Pridmore, Natalie E., Clayden, Jonathan
• Format: Journal Article
• Language: English
• Published: American Chemical Society 30.08.2023
• Subjects: enantiomerism; enantiomers; ethylene; hydrogen; hydrogen bonding; spectroscopy; stereochemistry; urea; X-ray diffraction

Cyclic triureas derived from 1,4,7-triazacyclononane (TACN) were synthesized; X-ray crystallography showed a chiral bowl-like conformation with each urea hydrogen-bonded to its neighbor with uniform directionality, forming a “cyclochiral” closed loop of hydrogen bonds. Variable-temperature 1H NMR, 1...