Ab initio and 17O NMR study of aromatic compounds with dicoordinate oxygen atoms. 1. Methoxy- and (methylenedioxy)benzene derivatives

¹⁷O NMR data at natural abundance in toluene-d8 at 74°C were obtained for aromatic compounds containing methoxy and methylenedioxy groups as side-chains substituents. ¹⁷O chemical shifts of this series of compounds are significantly influenced by both electronic and steric effects. Ortho electronic and steric substituent chemical shift effects for methoxy and methylenedioxy groups were estimated. Ab initio calculations at the 4-31G level were used to determine geometries of the compounds to gain insight into the structural aspects of these compounds. A correlation between the calculated bond orders, PCAr-O, and the ¹⁷O chemical shift was found. © 1990 American Chemical Society.

Duke Scholars

Author Julio Cesar Facelli Biostatistics & Bioinformatics, Division of Translational Bi ...