Hydrogen bonding and short contacts in [2,4,6-tris(trifluoromethyl)phenyl]phosphinic acid

Abstract

In the title compound, C(9)H(4)F(9)O(2)P, molecules are linked by a single O-H...O hydrogen bond into chains related to those in phenylphosphinic acid. There are short intramolecular F...P contacts.

P–C bond formation via P–H addition of a fluoroaryl phosphinic acid to ketones

“…In general phosphinic acids form strong hydrogen bonds owing to the polarity of the P–O unit. In 2a this is further enhanced resulting in very short donor acceptor distances, which is significantly shorter than in phenyl phosphinic acid (4) [28], but also shorter than in [2,4,6-tris(trifluoromethyl)phenyl]-phosphinic acid (5) [29]. A summary of the donor acceptor geometry parameters is given in Table 1.…”

Stereochemically inactive lone pairs in phosphorus(iii) compounds: the characterisation of some derivatives with the 2,5-(CF3)2C6H3 (Ar) substituent and their complexation behaviour towards Pt(ii) species

“…The bulky electron-withdrawing ligand 2,4,6-(CF 3 ) 3 C 6 H 2 (fluoromes) has been used extensively in recent years to stabilise both main group and transition metal species, 1 including phosphorus compounds, some of which have been structurally characterised. 2- 15 The combination of steric bulk in the orthopositions and the electron-withdrawing ability of the -CF 3 substituents enables many derivatives to be isolated which would be thermodynamically unstable, but are stabilised kinetically. This stability often seems to be enhanced by secondary short contacts between the central element and one or more fluorines of the ortho-CF 3 groups.…”

“…This stability often seems to be enhanced by secondary short contacts between the central element and one or more fluorines of the ortho-CF 3 groups. 12, 15 Less work has been carried out using the 2,6-(CF 3 ) 2 C 6 H 3 group, for good reasons. 14,[16][17][18][19][20] While this ligand, too, is strongly electron-withdrawing and has bulky ortho-substituents, synthesis of its derivatives is usually accomplished via lithiation of the hydrocarbon precursor 1,3-bis(trifluoromethyl)benzene.…”