Influence of the haloaryl moiety over the molecular packing in N-phenacylbenzimidazoles crystallizing in the same space group
| Autor: | Mario A. Macías, Diana Vargas-Oviedo, Jaime Portilla |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
010405 organic chemistry
Hydrogen bond Chemistry Aryl Hirshfeld surface maps Organic Chemistry Methylene bridge Crystal structure 010402 general chemistry Ring (chemistry) 01 natural sciences Cocrystal Benzimidazole 0104 chemical sciences Analytical Chemistry Inorganic Chemistry chemistry.chemical_compound Crystallography Intramolecular force Halogen Molecular packing Spectroscopy N -Phenacylbenzimidazoles |
| Zdroj: | Repositorio U. El Bosque Universidad El Bosque instacron:Universidad El Bosque |
| Popis: | In this study, a family of N -phenacylbenzimidazoles 1–3 synthesized in high yields (90–93%) by the N - phenacylation reaction of NH -benzimidazole ( 4 ) under ultrasonic conditions was recrystallized from the mixture EtOH:AcOEt (1:1 V/V). These compounds crystallize in the same Monoclinic P 2 1 / c space group, though the molecular packing is affected by the haloaryl group varying the final crystal structure. The para substitution of the halogen atom in the aryl ring influences a more pronounced electronic defi- ciency over the methylene bridge allowing the formation of intermolecular C–H ···O hydrogen bonds in compounds 1 and 3 . Additionally, in compound 2 , the ortho substitution of an F atom, not only affects the electron density but also blocks this CH 2 group with an intramolecular C–H ···O hydrogen bond. Re- markably after the crystallization process, compound 3 crystallizes as a cocrystal with a 4-fluorobenzoic acid molecule obtained by hydrolysis of 3 . This co-crystallization affects dramatically the total packing energies from values of -138.7/-135.2 kJ/mol for 1 and 2 , respectively, to -229.7 kJ/mol for compound 3 . |
| Databáze: | OpenAIRE |
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