Aromatic C-H-O Interactions in a Series of Bindone Analogues.NMR and Quantum Mechanical Study

摘要

The aromatic C-H…0 hydrogen bonding within the series of the structurally relative indenone derivatives has been studied.The presence of the hydrogen bonds is corroborated by the large low-field chemical shifts of the protons involved in the hydrogen bond observed experimentally and reproduced by quantum mechanical calculations.Further confirmation is provided by analysis of the orbital overlap coefficients,~(13)C NMR chemical shifts,and one-bond spin-spin coupling constants J(~(13)C-~1H).The relationship between molecular geometry and ~1H NMR chemical shifts of involved protons has a complex nature,but the C-H…O distance is the principal factor.