NMR study on structure elucidation of new imidazole ligands
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MOLDOVEANU, Costel, ZBANCIOC, Gheorghita N., AMĂRIUCĂI-MANTU, Dorina, MANGALAGIU, Ionel. NMR study on structure elucidation of new imidazole ligands. In: Physical Methods in Coordination and Supramolecular Chemistry, 24-26 octombrie 2012, Chişinău. Chisinau, Republic of Moldova: 2012, XVII, p. 114.
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Physical Methods in Coordination and Supramolecular Chemistry
XVII, 2012
Conferința ""Physical Methods in Coordination and Supramolecular Chemistry""
Chişinău, Moldova, 24-26 octombrie 2012

NMR study on structure elucidation of new imidazole ligands


Pag. 114-114

Moldoveanu Costel, Zbancioc Gheorghita N., Amăriucăi-Mantu Dorina, Mangalagiu Ionel
 
Alexandru Ioan Cuza University of Iaşi
 
 
Disponibil în IBN: 28 mai 2020


Rezumat

Imidazoles are common scaffolds in highly significant biomolecules, including biotin, the essential amino acid histidine, histamine, the pilocarpine alkaloids [1], and other alkaloids, which have been shown to exhibit interesting biological activities such as antimicrobial, and cytotoxic activities [2]. Imidazole derivatives have also been found to possess many other pharmacological properties and are widely implicated in biochemical processes. Recent advances in green chemistry and organometallic chemistry have extended the boundary of imidazoles to the synthesis and application of a large class of imidazoles as imidazole related N-heterocyclic carbenes (NHC) [3], due to the fact that these NHC can stabilize both high as well as low oxidation metal ions and form stable carbene complexes with a wide range of metal ions. Having in view these considerations our goal is to design and synthesize new imidazole based ligands which can be used as intermediates in the synthesis of imidazole related N-heterocyclic carbenes. The syntheses of imidazole based ligands occur in two steps: the synthesis of aliphatic spacers; and the synthesis of bis-imidazole derivatives with aliphatic spacer. The aliphatic spacers consist of bis-halogenoderivatives and were obtained by the reaction of chloroacylchlorides with aliphatic diaminoderivatives.formulaFor the synthesis of bis-imidazole derivatives with aliphatic spacer we used the reaction of the bis-halogenoderivatives previously obtained with sodium imidazolate.formulaFor the elucidation of the new compounds structure we were used elemental (C, H, N) and spectral analysis (IR, NMR). For more accurately proton and carbon assignment in NMR spectra we used a number of 1D and 2D experiments: 1H, 13C, DEPT, 2DCOSY, HMQC and HMBC. All the elemental and spectral data are in accordance with the proposed structure.

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<description xml:lang='en' descriptionType='Abstract'><p>Imidazoles are common scaffolds in highly significant biomolecules, including biotin, the essential amino acid histidine, histamine, the pilocarpine alkaloids [1], and other alkaloids, which have been shown to exhibit interesting biological activities such as antimicrobial, and cytotoxic activities [2]. Imidazole derivatives have also been found to possess many other pharmacological properties and are widely implicated in biochemical processes. Recent advances in green chemistry and organometallic chemistry have extended the boundary of imidazoles to the synthesis and application of a large class of imidazoles as imidazole related N-heterocyclic carbenes (NHC) [3], due to the fact that these NHC can stabilize both high as well as low oxidation metal ions and form stable carbene complexes with a wide range of metal ions. Having in view these considerations our goal is to design and synthesize new imidazole based ligands which can be used as intermediates in the synthesis of imidazole related N-heterocyclic carbenes. The syntheses of imidazole based ligands occur in two steps: the synthesis of aliphatic spacers; and the synthesis of bis-imidazole derivatives with aliphatic spacer. The aliphatic spacers consist of bis-halogenoderivatives and were obtained by the reaction of chloroacylchlorides with aliphatic diaminoderivatives.</p><p>formula</p><p>For the synthesis of bis-imidazole derivatives with aliphatic spacer we used the reaction of the bis-halogenoderivatives previously obtained with sodium imidazolate.</p><p>formula</p><p>For the elucidation of the new compounds structure we were used elemental (C, H, N) and spectral analysis (IR, NMR). For more accurately proton and carbon assignment in NMR spectra we used a number of 1D and 2D experiments: 1H, 13C, DEPT, 2DCOSY, HMQC and HMBC. All the elemental and spectral data are in accordance with the proposed structure.</p></description>
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