Fig. 5: Deuterium-labeling studies.
From: A robust and tunable halogen bond organocatalyzed 2-deoxyglycosylation involving quantum tunneling

Deuterated experiments confirming step-wise mechanism through deuterium scrambling and ascertaining source of C2 proton originates from the glycosyl acceptor. Intermolecular competition experiments to understand primary and secondary kinetic isotopic effects (KIEs), and KIE elevation to support quantum tunneling.