O–H.π(arene) intermolecular hydrogen bonding in the structure of 1,1,2-triphenylethanol

Abstract

The 1,1,2-triphenylethanol molecule, Ph2(PhCH2)COH (

Molecules isoelectronic with triphenylmethanol: diphenyl(4-pyridyl)methanol and triphenylmethylamine

“…With only modest changes in the steric demands at the unique central C atom, while keeping the number of hydrogen-bond donors and acceptors unchanged, the pattems of hydrogen bonding can be altered drastically. Thus in 1,1,2-triphenylethanol there is O--H...Tr(arene), rather than O--H...O, intermolecular hydrogen bonding (Ferguson, Gallagher, Glidewell & Zakaria, 1994), while the crystal structures of 1,2,3-triphenyl-2-propanol and tribenzylmethanol contain no hydrogen bonds at all (Ferguson, Gallagher, Glidewell, Liles & Zakaria, 1993).…”

“…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 (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).…”

Racemic Bis(1-ferrocenylpropyl) Ether

“…Since LiA1H4 reduction of acylferrocenes FcCOR usually provides the racemic alcohols FcCH(OH)R (Ferguson, Gallagher, Glidewell & Zakaria, 1994;Glidewell, Klar, Lightfoot, Zakaria & Ferguson, 1996), the observation here of only RR and SS forms indicates effective stereoselectivity in the dehydration process. Within the molecules of (I), the principal features of interest, aside from the configuration at the stereogenic C atoms, are the structure of the central C--O--C bridge and the conformations of the ferrocene fragments.…”

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

“…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).…”