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 $Ph_3PO$

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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Abstract

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
Publication:	Tetrahedron: Asymmetry
Publisher:	Elsevier
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
URI:	http://eprints.iisc.ac.in/id/eprint/6388

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