173846-89-4Relevant academic research and scientific papers
9-Fluoro-18-hydroxy-[3.3]metacyclophane: Synthesis and estimation of a C-F...H-O hydrogen bond
Takemura, Hiroyuki,Kotoku, Masayuki,Yasutake, Mikio,Shinmyozu, Teruo
, p. 2019 - 2024 (2004)
A cyclophane composed of fluorobenzene and phenol units was synthesized in order to observe the C-F...H-O hydrogen bond. In the crystal structure, 20% of the molecule clearly shows the intramolecular hydrogen bond and the other 80% is free from hydrogen bonding. On the other hand, a distinct low-field shift of the phenolic OH proton was observed in the 1H NMR spectrum compared to that of the F-free analog. Furthermore, O-H...F through-space coupling was observed. From the results of the crystallographic analysis, IR, and NMR spectra, the C-F...H-O hydrogen bond energy of this system was estimated to be 0.84-3.7 kJ·mol-1. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
