A NOVEL MOLECULAR CLEFT BASED ON DIOXOCIN RING, PART I: SYNTHESIS AND CONFORMATIONAL ANALYSIS

摘要

The Molecular cleft 1 using 8-methyl-16H-dinaphtho[2,1-d:1,2-g][1,3]dioxocin-2,14-diol as a spacer was synthesized. Density functional calculations at B3LYP/6-31G level of theory indicates that 8-methyl-16H-dinaphtho[2,1-d:1,2-g][1,3]dioxocin, the central part of 1, could be populated in two stable conformations, i.e. BC and DB with difference in total energy of 0.12 kcal/mol. ~1H-NMR spectroscopy, based on geminal coupling constants, shows that DB form is the most populated conformation of 1 in solution.