Structures of tribenzylmethanol and 1,2,3-triphenyl-2-propanol

Abstract

The tribenzylmethanol molecule, (PhCH2)3COH, has approximate threefold symmetry in the solid state. The hydroxyl H atom is disordered unequally over three orientations and is not involved in hydrogen bonding. The 1,2,3-

Hydrogen bonding in α-ferrocenyl alcohols: structures of 1-ferrocenylethanol, 1-ferrocenyl-2-phenylethanol, 1-ferrocenyl-1-phenylpropan-1-ol, 1-ferrocenyl-1-phenyl-2-methylpropan-1-ol, 1-ferrocenyl-1-phenyl-2,2-dimethylpropan-1-ol, 1-ferrocenyl-1,2-diphenylethanol and diferrocenyl(phenyl)methanol

“…Each of these hydrogen sites is trans to one of the C--C bonds involving C1, so that there is perfect staggering about the C1--O1 bond: since the three organic substituents bonded to C1 are all different (phenyl, benzyl, ferrocenyl), equal population of the three hydroxyl hydrogen sites is not to be expected. Similar perfect staggering of disordered hydroxyl hydrogen sites occurs in tribenzylmethanol, (PhCH2)3COH (Ferguson, Gallagher, Glidewell & Zakaria, 1993a), where the molecules, although lying in general positions, exhibit approximate threefold rotational symmetry and the disordered sites are again unequally populated. In each of its three sites the hydroxyl H atom in (2f) forms a close contact with a carbon of one of the aromatic systems ( Fig.…”

C–H.I− interactions in ferrocene derivatives: structures of (Ferrocenylmethyl)triphenylphosphonium iodide and 1,1'-ferrocenediylbis(methyltriphenylphosphonium iodide) dichloromethane solvate (1/1)

“…O--H and N--H) donors, there are extensive C--H...I-interactions in both structures. Well documented cases of C--H...I-hydrogen bonding are relatively uncommon but C.-.I-distances in the range 3.7-3.9 A have been reported (Ferguson, Lough, McAlees & McCrindle, 1993;Ferguson et al, 1994c).…”

“…We are currently studying the molecular structures and hydrogen-bonding patterns of a range of ferrocene derivatives and have found recently that there are very extensive three-dimensional networks of C--H...Iinteractions in both [(C5Hs)Fe(CsHaCH2NMe3)]+.I -, (3), and [Fe(CsHaCH2NMe3)2]2+.2I -, (4) (Ferguson et al, 1994c). Here we describe the C--H...I-interactions in the crystal structures of two related salts [(CsH5)Fe(CsHaCH2PPh3)]÷.I -, (1), and [Fe(CsH4CH~-PPh3)212÷.2I -, (2), which contain triphenylphosphine substituents, whereas (3) and (4) contain trimethylamine groups.…”

2,2,2-Triphenylethanol: a hydrogen-bonded tetramer based upon a centrosymmetric R44(8) motif

“…The structure of Ph2(CH3)COH also contains O--H...Tr(arene) interactions, but these are intramolecular and the compound is monomeric (Sultanov, Shnulin & Mamedov, 1985b). In contrast to both Ph3COH and Ph2(PhCH2)COH, the introduction of further methylene spacer groups between the phenyl rings and the quaternary C atom in Ph(PhCH2)2COH and (PhCH2)3COH leads to structures which contain no hydrogen bonds (Ferguson, Gallagher, Glidewell & Zakaria, 1993b). We have now extended the series Phx(PhCHE)3-xCOH to 2,2,2-triphenylethanol, PhaC--CHE--OH (I), in which the methylene spacer group has been placed between the quaternary C atom and the hydroxyl group; the structure of this compound shows yet another hydrogen-bonding pattern.…”

“…The compounds Ph3MOH (M = C, Si, Ge) all crystallize as hydrogen-bonded tetramers but while Ph3COH forms an almost perfectly tetrahedral tetramer (Ferguson, Gallagher, Glidewell, Low & Scrimgeour, 1992), the tetramers of both Ph3SiOH (Puff, Braun & Reuter, 1991) and Ph3GeOH (Ferguson, Gallagher, Murphy, Spalding, Glidewell & Holden,_1992) contain puckered O-atom tings of approximate 4 ($4) symmetry; Ph2(C2Hs)COH forms similar 4 tetramers (Sultanov, Shnulin & Mamedov, 1985a). Although the dimers of Ph2(ferrocenyl)COH are formed by O--H...O hydrogen bonds giving fourmembered OHOH tings (Ferguson, Gallagher, Glidewell & Zakaria, 1993a), by contrast, in Ph2(PhCH2)COH the sole intermolecular interactions leading to dimer formation are O--H...Tr(arene) hydrogen bonds (Ferguson, Gallagher, Glidewell & Zakaria, 1994), while the dimers of Ph2(PhCHF)COH depend upon O--H...F hydrogen bonds (DesMarteau, Xu & Witz, 1992). The structure of Ph2(CH3)COH also contains O--H...Tr(arene) interactions, but these are intramolecular and the compound is monomeric (Sultanov, Shnulin & Mamedov, 1985b).…”