9-fluoro-18-hydroxy-[3.3]metacyclophane:: Synthesis and estimation of a C-F...H-O hydrogen bond

被引：38

作者：

Takemura, H

Kotoku, M

Yasutake, M

Shinmyozu, T

机构：

[1] Kyushu Univ, Fac Sci, Dept Chem, Chuo Ku, Fukuoka 8108560, Japan

[2] Kyushu Univ, Fac Sci, Dept Chem, Higashi Ku, Fukuoka 8108581, Japan

[3] Kyushu Univ, Inst Mat Chem & Engn, Higashi Ku, Fukuoka 8128581, Japan

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 2004卷 / 09期

关键词：

hydrogen bonds; fluorine; cyclophanes; X-ray diffraction;

D O I：

10.1002/ejoc.200300698

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 H-1 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). (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).

引用

页码：2019 / 2024

页数：6

共 49 条

[1] Significant inter- and intramolecular O-H•••FC hydrogen bonding [J].