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Updated: Jul 6, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Hydrogen bonding vs steric gearing in a hexasubstituted benzene
Jesse V Gavette1, Andrew L Sargent, William E Allen
1Department of Chemistry, Science and Technology Building, East Carolina University, Greenville, North Carolina 27858-4353, USA.
Abstract:
Treatment of hexakis(bromomethyl)benzene with excess NaN 3, followed by hydrogenation of the resultant polyazide, affords hexamine 3 in high yield. Coupling to six equivalents of nonanoic acid provides hexamide 5 without chromatographic purification. The NH resonance of 5 appears far downfield (approximately 9.7 ppm) in CDCl3 and is unaffected by changes in concentration or by addition of chloride or trifluoromethanesulfonate ions. DFT calculations predict that 5 exists as a bowl, with all six substituents intramolecularly H-bonded together on one side of the plane defined by the anchoring arene.
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