Role of hydrogen bonding in the selectivity of aromatic Mannich reaction of tyramines: Macrocyclization vs. linear condensation
| Autor: | Christian Díaz-Oviedo, Rodolfo Quevedo |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
010405 organic chemistry
Chemistry Hydrogen bond Organic Chemistry Ethylamines Intermolecular force Formaldehyde Ab initio 010402 general chemistry 01 natural sciences 0104 chemical sciences Analytical Chemistry Inorganic Chemistry chemistry.chemical_compound Computational chemistry Molecular orbital Selectivity Mannich reaction Spectroscopy |
| Zdroj: | Journal of Molecular Structure. 1202:127283 |
| ISSN: | 0022-2860 |
| DOI: | 10.1016/j.molstruc.2019.127283 |
| Popis: | Tyramines (β-(4-hydroxyphenyl)ethylamines) present intermolecular associations via O–H⋯N hydrogen bonds, leading to the formation of “macrocyclization templates” in solution, which account for the obtained macrocyclic products in the aromatic Mannich reaction of these compounds with formaldehyde. However, the intermolecular association of tyramine is strongly affected by the presence of 2-naphthol, and its reaction with formaldehyde produces Mannich bases with linear tricomponents instead of macrocyclic products. The preference of tyramines to associate with 2-naphthol rather than with themselves is explained with the aid of semi-empirical and ab initio chemical calculations for the proposed hydrogen-bond based complexes, from energetic and molecular orbitals approaches. |
| Databáze: | OpenAIRE |
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