Intramolecular non-bonded interaction between selenium and oxygen as revealed by 17O and 77Se NMR spectroscopy and natural bond orbital analysis

Abstract

¹⁷ O and ⁷⁷Se NMR spectroscopic measurement and natural bond orbital (NBO) analysis of 2-formyl- and 2-hydroxymethyl-benzeneselenenyl derivatives (ArSeX; X = Cl, Br, CN, SPh, SeAr, Me: Ar = C₆H₄CHO, C₆H₄CH₂OH) provided strong evidence for the intramolecular non-bonded interaction between selenium and oxygen due to orbital interaction between the oxygen lone pair and the low-lying σ*_SeX antibonding orbital (n_O → σ*_SeX).