American Chemical Society
jo1c01818_si_001.pdf (4.04 MB)

Synthesis and Characterization of 1‑Hydroxy-4,5-arene-Fused Tropylium Derivatives

Download (4.04 MB)
journal contribution
posted on 2021-09-14, 12:37 authored by Takuya Kodama, Yuki Kawashima, Kenta Uchida, Zhirong Deng, Mamoru Tobisu
The properties of 1-hydroxy-4,5-arene-fused tropyliums were assessed based on experimental and theoretical investigations. An X-ray crystallographic analysis revealed a decrease of bond alternation in the seven-membered ring of 1-hydroxy-4,5-benzotropylium derivatives compared with that of the parent 4,5-benzotropones, which is indicative of an increase in aromaticity upon protonation. NICS and AICD calculations also supported the increased aromaticity of 1-hydroxy-4,5-arene-fused tropylium. The pKa values for a series of 1-hydroxy-4,5-arene-fused tropylium derivatives were also determined.