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Synthèse et études conformationnelles de 1:1-[alpha-alpha-Nalpha-Bn-hydrazino]mères linéaires et cycliques

Abstract : This work describes the synthesis and the structural study of linear and cyclic 1:1-[alpha/alpha-Nalpha-Bn-hydrazino]mers. After having designed a general method to synthesize alpha-Nalpha-hydrazinoesters with various surrogates on the alpha nitrogen in solution, these were used to build linear and cyclic 1:1-[alpha/alpha-Nalpha-Bn-hydrazino]mers of varied length. Conformational studies resorting to NMR, IR and X-ray crystallography have shown that the presence of a supplementary nitrogen within the backbone enables to form intramolecular hydrogen bonds, leading to the formation of hydrazinoturns. Thus, the alternation of natural alpha-aminoacids and alpha-hydrazinoacids leads to the autostructuration of the linear oligomers through the formation of y-turns and hydrazinoturns, both in the hetero and homochiral series. In the cyclic series, an X-ray crystallography analysis revealed the formation of nanotubes in the solid state, through the stacking of heterochiral cyclotetramers. This conformation exists in toluene and dodecane and leads to the formation of a gel. Despite having no proof of its structure in the solid state, the gel formed by the heterochiral cyclohexamer in cyclohexane confirms a comparable auto-structuration. Finally, concentration- and temperature-dependant NMR and IR studies have revealed the dynamics of the formation of nanotubes. The study of the homochiral cyclotetramer has however shown that it was not able to form a gel. As the gel is indicative of an auto-structuration, this has led us to question the versatility of the macrocyclic 1:1-[alpha/alpha-Nalpha-Bn-hydrazino] backbone towards the formation of nanotubes
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Ralph-Olivier Moussodia. Synthèse et études conformationnelles de 1:1-[alpha-alpha-Nalpha-Bn-hydrazino]mères linéaires et cycliques. Alimentation et Nutrition. Université de Lorraine, 2012. Français. ⟨NNT : 2012LORR0230⟩. ⟨tel-01749392⟩

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