Summary of organic fluorine as hydrogen-bonding acceptor

4 Summary of organic fluorine as hydrogen-bonding acceptor 

it would be a far-reaching interaction rather than a genuine hydrogen bond controlled by the orbital. 

2 Hydrogen bonding of 0-fluorinated alcohols, its structural character, and utilization in organic syntheses 

Meanwhile, fluorinated alcohols cannot be good proton acceptors due to their electron-deficient lone pairs on the oxygen atoms. The (3 scale of both TFE and HFIP is 0.00, which is apparently smaller than those of ethanol (0.77), ether (0.47), water (0.18), or even toluene (0.11) [33]. Here, the (3 scale, i.e. the hydrogen-bond acceptor basicity of a solvent, describes the ability to accept a proton (donate an electron pair) in a solute-solvent hydrogen-bonding system [4]. These acidities (pFCa [31, 34]), hydrogen-bonding parameters (a and (3 scale 

Catalog Handbook of Fine Chemicals, Aldrich, Milwaukee, 1996. 

---