Intermolecular Aliphatic C-F•••H-C Interaction in the Presence of "Stronger" Hydrogen Bond Acceptors: Crystallographic, Computational, and IR Studies

被引：16
|
作者：
Pitts, Cody Ross [1 ]
Siegler, Maxime A. [1 ]
Lectka, Thomas [1 ]
机构：
[1] Johns Hopkins Univ, Dept Chem, 3400 North Charles St, Baltimore, MD 21218 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 07期
基金：
美国国家科学基金会;
关键词：
MOLECULES PERSPECTIVE; TERMINAL ALKYNES; CRYSTAL PACKING; GAS-PHASE; FLUORINE; ATOMS; HECOGENIN; CHEMISTRY; DIMERS;
D O I：
10.1021/acs.joc.7b00268
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An unprecedented intermolecular aliphatic C-F center dot center dot center dot H-C interaction was observed in the X-ray crystal structure of a fluorinated triterpenoid. Despite the notion of fluorine being a poor acceptor, computational and IR studies revealed this interaction to be a weak to moderate hydrogen bond with a C-H stretch vibration frequency blue-shifted by 14 cm(-1) and d(F-H) = 2.13 angstrom. In addition, the aliphatic C-F bond is the preferred acceptor in the presence of multiple, traditionally stronger oxygen-based hydrogen bond acceptors.
引用
收藏
页码：3996 / 4000
页数：5
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