Abstract
The reaction of di-chloro-dimethyl-silane with a polydentate Schiff base ligand derived from pyridoxal and 2-ethano-lamine yielded the macrocyclic silicon compound (8E,22E)-4,4,12,18,18,26-hexa-methyl-3,5,17,19-tetra-oxa-8,13,22,27-tetra-aza-4,18-disilatri-cyclo-[22.4.0.010,15]octa-cosa-1(24),8,10,12,14,22,25,27-octa-ene-11,25-diol, C24H36N4O6Si2. The asymmetric unit contains the half macrocycle with an intra-molecular O-H⋯N hydrogen bond between the imine nitro-gen atom and a neighbouring oxygen atom. The crystal structure is dominated by C-H⋯O and C-H⋯π inter-actions, which form a high ordered mol-ecular network.
Highlights
The heterocyclic aldehyde pyridoxal is one of the active forms of vitamin B6
The coordination chemistry of Schiff bases generated from amino acids and pyridoxal with transition metal ions has been investigated intensive (Christensen, 1957; Long et al, 1980; Dawes et al, 1982; Walz et al, 1983; Rao et al, 1985; Astheimer et al, 1985; Sykes et al, 1991; Costa Pessoa et al, 1999)
A quite similar macrocycle has been obtained from the reaction of a related pyridoxal-derived Schiff base and dichlorodiphenylsilane (Bohme et al, 2008)
Summary
The heterocyclic aldehyde pyridoxal is one of the active forms of vitamin B6. This vitamin is an essential cofactor to a large number of enzymes that catalyze many reactions of amino acids (Sykes et al, 1991). We prepared a Schiff base from pyridoxal and 2-aminoethanol as a potential O,N,O-ligand. There are several potential coordination sites at the ligand molecule (I): the pyridine and the imino nitrogen atoms, two aliphatic and one phenolic hydroxyl groups. The presence of these functional groups makes it difficult to predict the structure of the reaction product with dichlorodimethylsilane. Recrystallization of the raw product from 1,2-dimethoxyethane and diethyl ether gave yellow crystals suitable for structure analysis
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