Pathology

Organic chemistry

Thiocyanate

Reactivity (psychology)

Halogen

Stereochemistry

Crystallography

Solid-state

Physical chemistry

Halogen bond

Inorganic chemistry

Chemistry

Alternative medicine

Alkyl

Medicine

Organic Chemistry Frontiers

The reactivity of [Ar1Ar2I](SCN) toward the solid-state arylation depends on the preorganization of halogen bond (XB)-bound SCN−: <italic>N</italic>-XB-bound thiocyanates, which, in contrast to <italic>N</italic>,<italic>S</italic>-XB-bound, undergoes the extremely rare <italic>N</italic>-arylation of SCN−.

Diaryliodonium as a double σ-hole donor: the dichotomy of thiocyanate halogen bonding provides divergent solid state arylation by diaryliodonium cations