Synthesis and Solvatochromism of Oxazolone Derivative: Combining Organic Synthesis and Physical Organic Chemistry in a Single Experiment
This work presents a proposal of experimental activity involving organic synthesis and solvatochromism of an organic molecule, correlating the content of organic chemistry and physical organic chemistry. This experiment presents a good opportunity to work with the classroom some of the content relat...
| Autores: | , , |
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| Formato: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2022 |
| País: | Brasil |
| Recursos: | Universidade Federal de Mato Grosso do Sul (UFMS) |
| Repositorio: | Orbital - The Electronic Journal of Chemistry (Campo Grande) |
| Idioma: | inglés |
| OAI Identifier: | oai:periodicos.ufms.br:article/16293 |
| Acesso em linha: | https://periodicos.ufms.br/index.php/orbital/article/view/16293 |
| Access Level: | acceso abierto |
| Palavra-chave: | Absorption spectra Azlactones Experimental class Solvent effects Spectroscopy |
| Resumo: | This work presents a proposal of experimental activity involving organic synthesis and solvatochromism of an organic molecule, correlating the content of organic chemistry and physical organic chemistry. This experiment presents a good opportunity to work with the classroom some of the content related to the mechanisms of organic reactions and the relationship between energy, electronic states, solute-solvent interactions, spectroscopy, among others in the area of physical chemistry, thus integrating knowledge. Experimentally, we synthesized through the Plöchl-Erlenmeyer method the oxazolonic derivative 4-[(p-N,N-dimethylamino)benzylidene]-2-phenyloxazole-5-one (AZA2) with good yield (78%), while the solvatochromic study showed that this derivative presented reverse solvatochromism; since in non-hydroxyl solvents it presented positive solvatochromism, but in protic solvents it presented negative solvatochromism. These different behaviors can be justified by the different solute-solvent interactions existing in each medium, which favors the prevalence of different mesomeric structures. |
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