Synthesis of a Symmetrical <i>tris</i>-Tetrazole as Isostere of a Tricarboxylic Acid: Behind New Tridentate Ligands for MOFs
The synthesis and characterization of three tridentate ligands for new MOFs are described. A triple aminolysis of the 1,3,5-tribenzoyl chloride with <i>p</i>-aminobenzoic acid gave the tricarboxylic acid <b>3</b> in 90% yield. Moreover, the same reaction, also from the 1,3,5-...
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MDPI AG
2021-11-01
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| author | Julio C. Flores-Reyes Perla Islas-Jácome Atilano Gutiérrez-Carrillo Mónica A. Rincón-Guevara Galdina V. Suárez-Moreno Óscar Vázquez-Vera Leticia Lomas-Romero Eduardo González-Zamora Alejandro Islas-Jácome |
| author_facet | Julio C. Flores-Reyes Perla Islas-Jácome Atilano Gutiérrez-Carrillo Mónica A. Rincón-Guevara Galdina V. Suárez-Moreno Óscar Vázquez-Vera Leticia Lomas-Romero Eduardo González-Zamora Alejandro Islas-Jácome |
| author_sort | Julio C. Flores-Reyes |
| collection | DOAJ |
| description | The synthesis and characterization of three tridentate ligands for new MOFs are described. A triple aminolysis of the 1,3,5-tribenzoyl chloride with <i>p</i>-aminobenzoic acid gave the tricarboxylic acid <b>3</b> in 90% yield. Moreover, the same reaction, also from the 1,3,5-tribenzoyl chloride, but using <i>p</i>-aminobenzonitrile gave the new <i>tris</i>-benzonitrile <b>5</b> in 85% yield. Finally, this later one was treated with sodium azide and a Lewis acid to synthesize the new <i>tris</i>-tetrazole-based ligand <b>7</b> in 72% yield through a [3 + 2] azide-nitrile cycloaddition. It is noteworthy that the isosterism between carboxylic acids and tetrazoles may be considered to design and fabricate new MOFs with similar properties. |
| first_indexed | 2024-03-11T06:46:27Z |
| format | Article |
| id | doaj.art-2ddabc3cb8ac44f7b9992594a60c50f3 |
| institution | Directory Open Access Journal |
| issn | 2673-4583 |
| language | English |
| last_indexed | 2024-03-11T06:46:27Z |
| publishDate | 2021-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Chemistry Proceedings |
| spelling | doaj.art-2ddabc3cb8ac44f7b9992594a60c50f32023-11-17T10:18:23ZengMDPI AGChemistry Proceedings2673-45832021-11-01812510.3390/ecsoc-25-11751Synthesis of a Symmetrical <i>tris</i>-Tetrazole as Isostere of a Tricarboxylic Acid: Behind New Tridentate Ligands for MOFsJulio C. Flores-Reyes0Perla Islas-Jácome1Atilano Gutiérrez-Carrillo2Mónica A. Rincón-Guevara3Galdina V. Suárez-Moreno4Óscar Vázquez-Vera5Leticia Lomas-Romero6Eduardo González-Zamora7Alejandro Islas-Jácome8Departamento de Química, Universidad Autónoma Metropolitana-Iztapalapa, Avenida Ferrocarril San Rafael Atlixco, Número 186, Colonia Leyes de Reforma 1A Sección, Alcaldía Iztapalapa, Ciudad de México 09310, MexicoDepartamento de Química, Universidad Autónoma Metropolitana-Iztapalapa, Avenida Ferrocarril San Rafael Atlixco, Número 186, Colonia Leyes de Reforma 1A Sección, Alcaldía Iztapalapa, Ciudad de México 09310, MexicoDepartamento de Química, Universidad Autónoma Metropolitana-Iztapalapa, Avenida Ferrocarril San Rafael Atlixco, Número 186, Colonia Leyes de Reforma 1A Sección, Alcaldía Iztapalapa, Ciudad de México 09310, MexicoDepartamento de Biotecnología, Universidad Autónoma Metropolitana-Iztapalapa, Avenida Ferrocarril San Rafael Atlixco, Número 186, Colonia Leyes de Reforma 1A Sección, Alcaldía Iztapalapa, Ciudad de México 09310, MexicoInstituto Politécnico Nacional, Unidad Profesional Interdisciplinaria de Biotecnología, Av. Acueducto S/N, Barrio la Laguna Ticomán, Ciudad de México 07340, MexicoInstituto Politécnico Nacional, Unidad Profesional Interdisciplinaria de Biotecnología, Av. Acueducto S/N, Barrio la Laguna Ticomán, Ciudad de México 07340, MexicoDepartamento de Química, Universidad Autónoma Metropolitana-Iztapalapa, Avenida Ferrocarril San Rafael Atlixco, Número 186, Colonia Leyes de Reforma 1A Sección, Alcaldía Iztapalapa, Ciudad de México 09310, MexicoDepartamento de Química, Universidad Autónoma Metropolitana-Iztapalapa, Avenida Ferrocarril San Rafael Atlixco, Número 186, Colonia Leyes de Reforma 1A Sección, Alcaldía Iztapalapa, Ciudad de México 09310, MexicoDepartamento de Química, Universidad Autónoma Metropolitana-Iztapalapa, Avenida Ferrocarril San Rafael Atlixco, Número 186, Colonia Leyes de Reforma 1A Sección, Alcaldía Iztapalapa, Ciudad de México 09310, MexicoThe synthesis and characterization of three tridentate ligands for new MOFs are described. A triple aminolysis of the 1,3,5-tribenzoyl chloride with <i>p</i>-aminobenzoic acid gave the tricarboxylic acid <b>3</b> in 90% yield. Moreover, the same reaction, also from the 1,3,5-tribenzoyl chloride, but using <i>p</i>-aminobenzonitrile gave the new <i>tris</i>-benzonitrile <b>5</b> in 85% yield. Finally, this later one was treated with sodium azide and a Lewis acid to synthesize the new <i>tris</i>-tetrazole-based ligand <b>7</b> in 72% yield through a [3 + 2] azide-nitrile cycloaddition. It is noteworthy that the isosterism between carboxylic acids and tetrazoles may be considered to design and fabricate new MOFs with similar properties.https://www.mdpi.com/2673-4583/8/1/25metal-organic frameworks (MOFs)tridentate ligandstricarboxylic acids<i>tris</i>-benzonitriles<i>tris</i>-tetrazolesaminolysis |
| spellingShingle | Julio C. Flores-Reyes Perla Islas-Jácome Atilano Gutiérrez-Carrillo Mónica A. Rincón-Guevara Galdina V. Suárez-Moreno Óscar Vázquez-Vera Leticia Lomas-Romero Eduardo González-Zamora Alejandro Islas-Jácome Synthesis of a Symmetrical <i>tris</i>-Tetrazole as Isostere of a Tricarboxylic Acid: Behind New Tridentate Ligands for MOFs Chemistry Proceedings metal-organic frameworks (MOFs) tridentate ligands tricarboxylic acids <i>tris</i>-benzonitriles <i>tris</i>-tetrazoles aminolysis |
| title | Synthesis of a Symmetrical <i>tris</i>-Tetrazole as Isostere of a Tricarboxylic Acid: Behind New Tridentate Ligands for MOFs |
| title_full | Synthesis of a Symmetrical <i>tris</i>-Tetrazole as Isostere of a Tricarboxylic Acid: Behind New Tridentate Ligands for MOFs |
| title_fullStr | Synthesis of a Symmetrical <i>tris</i>-Tetrazole as Isostere of a Tricarboxylic Acid: Behind New Tridentate Ligands for MOFs |
| title_full_unstemmed | Synthesis of a Symmetrical <i>tris</i>-Tetrazole as Isostere of a Tricarboxylic Acid: Behind New Tridentate Ligands for MOFs |
| title_short | Synthesis of a Symmetrical <i>tris</i>-Tetrazole as Isostere of a Tricarboxylic Acid: Behind New Tridentate Ligands for MOFs |
| title_sort | synthesis of a symmetrical i tris i tetrazole as isostere of a tricarboxylic acid behind new tridentate ligands for mofs |
| topic | metal-organic frameworks (MOFs) tridentate ligands tricarboxylic acids <i>tris</i>-benzonitriles <i>tris</i>-tetrazoles aminolysis |
| url | https://www.mdpi.com/2673-4583/8/1/25 |
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