We describe a general approach to computational investigation of electrophilic addition of hydrogen halides to alkenes and alkynes that involves the formation of π-complex, with natural bond theory (NBO) and natural resonance theory (NRT), allowing insights from modern quantum chemical descriptors and spectroscopy. In this work, we present computed NRT weightings and bond orders, which show the resonance-type visualization of the electronic nature of π-complex intermediate during electrophilic addition reaction. We demonstrate that the formation π-complex is primary due to the short range covalency hydrogen bonding by delocalization of pi-electrons (πCC) from donor alkene/alkyne (Lewis-base) to proximal H-X antibond (σ*HX) of an acceptor (Lewis-acid).

Examining the nature of π- complex intermediate for electrophilic addition of hydrogen halides to alkenes and alkynes

ACS Spring 2022

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