A simple concept taught in general chemistry, hydrogen bonding is ubiquitous throughout chemistry and biology. An intriguing and relatively young subset of this field sees transition metals as hydrogen bond acceptors. Despite extensive evidence of platinum’s participation in hydrogen bonding, neighboring gold is underdeveloped in this field. Examples of intramolecular hydrogen bonding with gold are limited to recent experimental evidence for Au●●●H-N hydrogen bonding and a computational report of Au●●●H-O hydrogen bonding. To provide experimental evidence for Au●●●H-O hydrogen bonding and to further understand gold’s role in this interaction, we have synthesized and characterized a series of Au(I) carbinols exhibiting intramolecular Au●●●H-O hydrogen bonding. By varying the donicity of the ligands on gold, we are able to modulate the metallobasicity of the metal center, thereby tuning the strength of this interaction. In addition to crystal structures, we have also studied these systems using NMR and IR spectroscopy. Optimization and frequency calculations corroborate the structures of these compounds. Further understanding of these compounds’ electronic structures was obtained through NBO and AIM analyses. This work experimentally establishes Au●●●H-O hydrogen bonding and provides insight into how this interaction may be finely tuned using gold’s electronic structure.

Experimental evidence for intramolecular Au H-O hydrogen bonding

ACS Fall 2021

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