Chandrasekhar, Sosale and Kulkarni, Guruprasad and Muktha, B and Guru Row, Tayur N (2003) A complex of Ph3PO with a chiral hydrogen-bond donor: X-ray crystal structures of the complexes with (RS)-(±)- and (S)-(−)-1,1'-bi-2,2'-naphthol: homochiral $Ph_3PO$. In: Tetrahedron: Asymmetry, 14 (23). pp. 3769-3772.
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The first complex of triphenylphosphine oxide $(Ph_3PO)$ with a chiral substrate, formed by crystallising Ph3PO in the presence of the synthetically important chiral auxiliary S-(-)-1,1'-bi-2,2'-naphthol (BINOL) is reported. The corresponding racemate form has also been prepared and the single-crystal X-ray diffraction structures of both reveal 1(BINOL):2(TPPO) stoichiometry. In the homochiral complex the TPPO molecules apparently exist in one enantiomeric form only. Crystal packing in both is dominated by intermolecular hydrogen bonding between a BINOL hydroxyl group and a TPPO oxygen atom (around $2_1$ and $3_1$ axes in the racemate and the chiral forms respectively). The crystalline racemate—a racemic compound rather than a conglomerate—is more densely packed than the homochiral form, thus apparently conforming to Wallach’s rule.
|Item Type:||Journal Article|
|Additional Information:||The Copyright belongs to Elsevier.|
|Department/Centre:||Division of Chemical Sciences > Solid State & Structural Chemistry Unit
Division of Chemical Sciences > Organic Chemistry
|Date Deposited:||21 Apr 2006|
|Last Modified:||19 Sep 2010 04:25|
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