Abstract
A series of diimines have been synthesized by coupling of diamine with substituted benzaldehydes. The purities of these diimines were checked by their analytical and spectroscopic data. The spectral frequencies νCN (cm-1), NMR chemical shifts (δ, ppm) of C-H and C=N of these diimines have been correlated with Hammett substituent constants, F and R parameters using single and multi-linear regression analysis. From the results of statistical analysis, the effect of substituents on the above spectral data has been studied. KEY WORDS: Diimines, IR and NMR spectra, Spectral correlation, Hammett sigma constants Bull. Chem. Soc. Ethiop. 2014, 28(1), 73-79.DOI: http://dx.doi.org/10.4314/bcse.v28i1.9
Highlights
In this decade synthesis of enantiometrically pure compounds from prochiral compounds using chiral reagents have become topic of immense interest
Aldehydes and ketones react with primary amines to give imines, in which the carbon-oxygen double bond is replaced by a carbon-nitrogen double bond was discovered in 1864 by Hugo Schiff [1] and been always the reaction of interest to chemists up to date in the fields of macrocyclic and supramolecular chemistry
Primary amine and β-diketones used for synthesis of cyclic diimines
Summary
In this decade synthesis of enantiometrically pure compounds from prochiral compounds using chiral reagents have become topic of immense interest. Numerous solvent assisted [2] or solvent free greener [3] methods and reagents were available in the literature for synthesis of optically active diimines. These diimines have been used as a precursor for synthesis of optically active cyclic imines like piperazine derivatives [4], heterocycles such as imidazolines, pyrimidines, carbapenem intermediates, bis-β-lactams, bisketenes [5, 6], polymers[7] and many metal complexes[8]. Suresh et al, [12] have studied the effects of substituent on infrared C=N, nuclear magnetic resonance chemical shifts (ppm) δCH and CN In this work they observed good, satisfactory and fair degree of correlations for the above frequencies with Hammett substituent constants, F and R parameters. The author has taken efforts to synthesis and studied the effect of substituents on the spectral group frequencies of synthesized diimines
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