Synthesis, Characterization, and DFT Calculations of a New Sulfamethoxazole Schiff Base and Its Metal Complexes
A new Schiff base, 4-((1E,2E)-3-(furan-2-yl)allylidene)amino)-N-(5-methylisoxazol-3-yl) benzene-sulfonamide (L), was synthesized by thermal condensation of 3-(2-furyl)acrolein and sulfamethoxazole (SMX), and the furan Schiff base (L) was converted to a phenol Schiff base (L’) according to the Diels–...
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| author | Jibril I. Al-Hawarin Abdel-Aziz Abu-Yamin Abd Al-Aziz A. Abu-Saleh Ibrahim A. M. Saraireh Mansour H. Almatarneh Mahmood Hasan Omar M. Atrooz Y. Al-Douri |
| author_facet | Jibril I. Al-Hawarin Abdel-Aziz Abu-Yamin Abd Al-Aziz A. Abu-Saleh Ibrahim A. M. Saraireh Mansour H. Almatarneh Mahmood Hasan Omar M. Atrooz Y. Al-Douri |
| author_sort | Jibril I. Al-Hawarin |
| collection | DOAJ |
| description | A new Schiff base, 4-((1E,2E)-3-(furan-2-yl)allylidene)amino)-N-(5-methylisoxazol-3-yl) benzene-sulfonamide (L), was synthesized by thermal condensation of 3-(2-furyl)acrolein and sulfamethoxazole (SMX), and the furan Schiff base (L) was converted to a phenol Schiff base (L’) according to the Diels–Alder [4 + 2] cycloaddition reaction and studied experimentally. The structural and spectroscopic properties of the Schiff base were also corroborated by utilizing density functional theory (DFT) calculations. Furthermore, a series of lanthanide and transition metal complexes of the Schiff base were synthesized from the nitrate salts of Gd, Sm, Nd, and Zn (L<b>1</b>, L<b>2</b>, L<b>3</b>, and L<b>4</b>), respectively. Various spectroscopic studies confirmed the chemical structures of the Schiff-base ligand and its complexes. Based on the spectral studies, a nine-coordinated geometry was assigned to the lanthanide complexes and a six-coordinated geometry to the zinc complex. The elemental analysis data confirmed the suggested structure of the metal complexes, and the TGA studies confirmed the presence of one coordinated water molecule in the lanthanide complexes and one crystalline water molecule in the zinc complex; in addition, the conductivity showed the neutral nature of the complexes. Therefore, it is suggested that the ligand acts as a bidentate through coordinates to each metal atom by the isoxazole nitrogen and oxygen atoms of the sulfur dioxide moiety of the SMX based on FTIR studies. The ligand and its complexes were tested for their anti-inflammatory, anti-hemolytic, and antioxidant activities by various colorimetric methods. These complexes were found to exhibit potential effects of the selected biological activities. |
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| institution | Directory Open Access Journal |
| issn | 1996-1944 |
| language | English |
| last_indexed | 2024-03-11T00:53:12Z |
| publishDate | 2023-07-01 |
| publisher | MDPI AG |
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| series | Materials |
| spelling | doaj.art-c8111bfba7844c36af76859f595436b42023-11-18T20:18:52ZengMDPI AGMaterials1996-19442023-07-011614516010.3390/ma16145160Synthesis, Characterization, and DFT Calculations of a New Sulfamethoxazole Schiff Base and Its Metal ComplexesJibril I. Al-Hawarin0Abdel-Aziz Abu-Yamin1Abd Al-Aziz A. Abu-Saleh2Ibrahim A. M. Saraireh3Mansour H. Almatarneh4Mahmood Hasan5Omar M. Atrooz6Y. Al-Douri7Department of Chemistry, Al-Hussein Bin Talal University, Ma’an 71111, JordanDepartment of Chemistry, Al-Hussein Bin Talal University, Ma’an 71111, JordanDepartment of Chemistry, Memorial University, St. John’s, NL A1B 3X7, CanadaDepartment of Chemistry, Al-Hussein Bin Talal University, Ma’an 71111, JordanDepartment of Chemistry, Memorial University, St. John’s, NL A1B 3X7, CanadaHepi Company (Home of Experience) for Paints and Inks, Cairo 61710, EgyptDepartment of Biological Sciences, Mutah University, Mutah 617102, JordanNanotechnology and Catalysis Research Center (NANOCAT), University of Malaya, Kuala Lumpur 50603, MalaysiaA new Schiff base, 4-((1E,2E)-3-(furan-2-yl)allylidene)amino)-N-(5-methylisoxazol-3-yl) benzene-sulfonamide (L), was synthesized by thermal condensation of 3-(2-furyl)acrolein and sulfamethoxazole (SMX), and the furan Schiff base (L) was converted to a phenol Schiff base (L’) according to the Diels–Alder [4 + 2] cycloaddition reaction and studied experimentally. The structural and spectroscopic properties of the Schiff base were also corroborated by utilizing density functional theory (DFT) calculations. Furthermore, a series of lanthanide and transition metal complexes of the Schiff base were synthesized from the nitrate salts of Gd, Sm, Nd, and Zn (L<b>1</b>, L<b>2</b>, L<b>3</b>, and L<b>4</b>), respectively. Various spectroscopic studies confirmed the chemical structures of the Schiff-base ligand and its complexes. Based on the spectral studies, a nine-coordinated geometry was assigned to the lanthanide complexes and a six-coordinated geometry to the zinc complex. The elemental analysis data confirmed the suggested structure of the metal complexes, and the TGA studies confirmed the presence of one coordinated water molecule in the lanthanide complexes and one crystalline water molecule in the zinc complex; in addition, the conductivity showed the neutral nature of the complexes. Therefore, it is suggested that the ligand acts as a bidentate through coordinates to each metal atom by the isoxazole nitrogen and oxygen atoms of the sulfur dioxide moiety of the SMX based on FTIR studies. The ligand and its complexes were tested for their anti-inflammatory, anti-hemolytic, and antioxidant activities by various colorimetric methods. These complexes were found to exhibit potential effects of the selected biological activities.https://www.mdpi.com/1996-1944/16/14/5160Schiff basecharacterization3-(2-furyl)acroleinsulfamethoxazoleDFTlanthanide |
| spellingShingle | Jibril I. Al-Hawarin Abdel-Aziz Abu-Yamin Abd Al-Aziz A. Abu-Saleh Ibrahim A. M. Saraireh Mansour H. Almatarneh Mahmood Hasan Omar M. Atrooz Y. Al-Douri Synthesis, Characterization, and DFT Calculations of a New Sulfamethoxazole Schiff Base and Its Metal Complexes Materials Schiff base characterization 3-(2-furyl)acrolein sulfamethoxazole DFT lanthanide |
| title | Synthesis, Characterization, and DFT Calculations of a New Sulfamethoxazole Schiff Base and Its Metal Complexes |
| title_full | Synthesis, Characterization, and DFT Calculations of a New Sulfamethoxazole Schiff Base and Its Metal Complexes |
| title_fullStr | Synthesis, Characterization, and DFT Calculations of a New Sulfamethoxazole Schiff Base and Its Metal Complexes |
| title_full_unstemmed | Synthesis, Characterization, and DFT Calculations of a New Sulfamethoxazole Schiff Base and Its Metal Complexes |
| title_short | Synthesis, Characterization, and DFT Calculations of a New Sulfamethoxazole Schiff Base and Its Metal Complexes |
| title_sort | synthesis characterization and dft calculations of a new sulfamethoxazole schiff base and its metal complexes |
| topic | Schiff base characterization 3-(2-furyl)acrolein sulfamethoxazole DFT lanthanide |
| url | https://www.mdpi.com/1996-1944/16/14/5160 |
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