Synthesis, crystal structures and spectral characterization of imidazo[1,2-a]pyrimidin-2-yl-acetic acid and related analog with imidazo[2,1-b]thiazole ring
| Autor: | Ewa Matczak-Jon, Michał Sowa, Piotr Drożdżewski, Agnieszka Dylong, Katarzyna Ślepokura, Waldemar Goldeman |
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| Rok vydání: | 2016 |
| Předmět: |
010405 organic chemistry
Hydrogen bond Stereochemistry Organic Chemistry Infrared spectroscopy Crystal structure 010402 general chemistry 01 natural sciences 0104 chemical sciences Analytical Chemistry Inorganic Chemistry chemistry.chemical_compound Crystallography symbols.namesake chemistry symbols Proton NMR Density functional theory Methylene Thiazole Raman spectroscopy Spectroscopy |
| Zdroj: | Journal of Molecular Structure. 1117:153-163 |
| ISSN: | 0022-2860 |
| Popis: | Imidazo[1,2- a ]pyrimidin-2-yl-acetic acid (H IPM-2-ac ) and its analog with imidazo[2,1- b ]thiazole ring (H ITZ-6-ac ) were synthesized and structurally characterized by single-crystal X-ray diffraction corroborated with calculations of Hirshfeld surfaces, which provided detailed insight into intermolecular interactions constituting both crystals. The IR and Raman spectra of H IPM-2-ac and H ITZ-6-ac were recorded and interpreted in details with the aid of Density Functional Theory (DFT) calculations and Potential Energy Distribution (PED) analysis of computed normal vibrations. Special attention was paid on hydroxyl and methylene groups involved in hydrogen bonds, which vibrations were monitored by H/D substitution. Recrystallization of parent compounds from deuterium oxide (D 2 O) solutions resulted in deuteration of their carboxylic OH groups and almost complete deuteration of H IPM-2-ac methylene group. The latter phenomenon is clearly reflected in the vibrational spectra and confirmed by 1 H NMR experiments in solution. |
| Databáze: | OpenAIRE |
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