Experimental and Computational Investigations of 4-((E)-(2-Amino-5- Nitrophenylimino)Methyl)-5- (Hydroxymethyl)-2-Methylpyridin-3-Ol Schiff Base Derived from Vitamin B6
| Autor: | Safar Ali Beyramabadi, Maryam Khashi, Hamed Chegini, Ali Morsali, Azar Gharib |
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| Rok vydání: | 2018 |
| Předmět: |
Schiff base
010405 organic chemistry Hydrogen bond Chemical shift Atoms in molecules 010402 general chemistry Condensation reaction 01 natural sciences Medicinal chemistry 0104 chemical sciences Inorganic Chemistry chemistry.chemical_compound chemistry Intramolecular force Materials Chemistry Density functional theory Hydroxymethyl Physical and Theoretical Chemistry |
| Zdroj: | Journal of Structural Chemistry. 59:1326-1334 |
| ISSN: | 1573-8779 0022-4766 |
| DOI: | 10.1134/s0022476618060112 |
| Popis: | An unsymmetrical tridentate Schiff base 4-((E)-(2-amino-5-nitrophenylimino)methyl)-5-(hydroxymethyl)- 2-methylpyridin-3-ol is newly synthesized and characterized experimentally. Its geometrical parameters, the assignment of IR bands and NMR chemical shifts are also computed by the density functional theory (DFT) method. In addition, the atoms in molecules (AIM) analysisis employed to investigate its geometry. Only one of the diamine–NH2 groups undergoes the condensation reaction. In the structure of the synthesized Schiff base, the remaining aminogroup lies in the para position with respect to the nitro group (isomer 1). In both gas and solution phases, isomer 1 is more stable than isomer 2 with the meta orientation of the amino and nitro groups. The NMR chemical shifts and the AIM analysis show that isomer 1 is a more favorite structure for the synthesized Schiff base. It has no planar structure. The phenolic proton is engaged in the intramolecular hydrogen bond with the azomethine nitrogen atom. The experimental results are in good agreement with the theoretical ones, confirming the validity of the optimized geometry. |
| Databáze: | OpenAIRE |
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