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 rela...
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| Format: | Article |
| Language: | English |
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Universidade Federal de Mato Grosso do Sul
2022-07-01
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| Series: | Orbital: The Electronic Journal of Chemistry |
| Subjects: | |
| Online Access: | https://periodicos.ufms.br/index.php/orbital/article/view/16293 |
| _version_ | 1797946931424526336 |
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| author | Taianne D’Angelo Korb Lucia Helena Franco Martires da Costa Mauricio Ferreira da Rosa |
| author_facet | Taianne D’Angelo Korb Lucia Helena Franco Martires da Costa Mauricio Ferreira da Rosa |
| author_sort | Taianne D’Angelo Korb |
| collection | DOAJ |
| description |
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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| first_indexed | 2024-04-10T21:18:50Z |
| format | Article |
| id | doaj.art-b135f3fd83b6471d8d5e6ceeeb645d44 |
| institution | Directory Open Access Journal |
| issn | 1984-6428 |
| language | English |
| last_indexed | 2024-04-10T21:18:50Z |
| publishDate | 2022-07-01 |
| publisher | Universidade Federal de Mato Grosso do Sul |
| record_format | Article |
| series | Orbital: The Electronic Journal of Chemistry |
| spelling | doaj.art-b135f3fd83b6471d8d5e6ceeeb645d442023-01-20T10:47:27ZengUniversidade Federal de Mato Grosso do SulOrbital: The Electronic Journal of Chemistry1984-64282022-07-0114210.17807/orbital.v14i2.16293Synthesis and Solvatochromism of Oxazolone Derivative: Combining Organic Synthesis and Physical Organic Chemistry in a Single Experiment Taianne D’Angelo Korb0Lucia Helena Franco Martires da Costa1Mauricio Ferreira da Rosa2Dept. of Chemistry, UNIOESTE, Toledo, Paraná, BrazilDept. of Chemistry, UNIOESTE, Toledo, Paraná, BrazilDept. of Chemistry, UNIOESTE, Toledo, Paraná, Brazil 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. https://periodicos.ufms.br/index.php/orbital/article/view/16293Absorption spectraAzlactonesExperimental classSolvent effectsSpectroscopy |
| spellingShingle | Taianne D’Angelo Korb Lucia Helena Franco Martires da Costa Mauricio Ferreira da Rosa Synthesis and Solvatochromism of Oxazolone Derivative: Combining Organic Synthesis and Physical Organic Chemistry in a Single Experiment Orbital: The Electronic Journal of Chemistry Absorption spectra Azlactones Experimental class Solvent effects Spectroscopy |
| title | Synthesis and Solvatochromism of Oxazolone Derivative: Combining Organic Synthesis and Physical Organic Chemistry in a Single Experiment |
| title_full | Synthesis and Solvatochromism of Oxazolone Derivative: Combining Organic Synthesis and Physical Organic Chemistry in a Single Experiment |
| title_fullStr | Synthesis and Solvatochromism of Oxazolone Derivative: Combining Organic Synthesis and Physical Organic Chemistry in a Single Experiment |
| title_full_unstemmed | Synthesis and Solvatochromism of Oxazolone Derivative: Combining Organic Synthesis and Physical Organic Chemistry in a Single Experiment |
| title_short | Synthesis and Solvatochromism of Oxazolone Derivative: Combining Organic Synthesis and Physical Organic Chemistry in a Single Experiment |
| title_sort | synthesis and solvatochromism of oxazolone derivative combining organic synthesis and physical organic chemistry in a single experiment |
| topic | Absorption spectra Azlactones Experimental class Solvent effects Spectroscopy |
| url | https://periodicos.ufms.br/index.php/orbital/article/view/16293 |
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