New or improved syntheses of the polyfluoroalcohols HOC(cyclo-C6H11)2(CF3), HO(cyclo-C6H11)(CF3)2, and HOC(Ar)(CF3)2 (Ar = 4-C6H4(t-Bu), 2,4,6-C6H2(CF3)3, 4-Si(i-Pr)3-2,6-C6H2(CF3)2, 3,5-C6H3(CH3)2), and 2-C6H4(C(OH)(CF3)2)

Is there any bona fide example of O–H⋯F–C bond in solution? The cases of HOC(CF3)2(4-X-2,6-C6H2(CF3)2) (X = Si(i-Pr)3, CF3)

“…The mononuclear structure A (Chart 1) was proposed, with significant intramolecular O-H … F 1 -C bonding causing slow rotation of the proximal CF 3 group at 296 uC, although the expected J( 1 H-19 F) coupling to F 1 was not observed. 7 A similar behavior was found for HOC(CF 3 ) 2 (2,4,6-C 6 H 2 (CF 3 ) 3 ), 8 showing that the ring substituent in para (Si(i-Pr) 3 or CF 3 ) position has no influence, whether electronic or steric, on the substituents that could be involved in H-bonding.…”

“…6 However, O-H … F-C hydrogen bond in solution has been proposed only for the molecules HOC(CF 3 ) 2 (4-X-2,6-C 6 H 2 (CF 3 ) 2 ) (X = Si(i-Pr) 3 , CF 3 ). 7,8 We show here that there is a misinterpretation of the spectroscopic evidence for these two molecules. This eliminates the only examples that have been taken so far as a reference for the existence of O-H … F-C hydrogen bonds in solution.…”

The intramolecular C–F⋯HO hydrogen bond of 2-fluorophenyldiphenylmethanol

“…8 However, there are a few observations of O-HÁ Á ÁF and N-HÁ Á ÁF interactions in solution. Recently, experimental O-HÁ Á ÁF evidence by Strauss et al 9 was denied by Espinet et al 10 On the other hand, N-HÁ Á ÁF hydrogen bonding-driven foldamers were found by Li et al 11 Other examples have been found by our group 1 and by Vasella et al (described below). 12 In such a situation, the role of the C-FÁ Á ÁHO hydrogen bond is somewhat subtle, and thus we must accumulate examples.…”

The first one-dimensional coordination polymer containing O–H⋯F–Ni hydrogen bonding: crystal structure of [Ni3(dpa)4F2][Ni3(dpa)4(H2O)2](BF4)2·2CH3OH

“…The O-HÁ Á ÁF hydrogen bonding has not been given much attention up until now. Recently, researches on the organic fluorine atoms as hydrogen bonding acceptor are in the process [26][27][28][29][30][31][32]. However, no example of coordination polymer containing the O-HÁ Á ÁF-Ni hydrogen bond can be found in the literatures or CSD.…”