Synthesis, Characterization, Semiempirical and Biological Activities of Organotin(IV) Carboxylates with 4-Piperidinecarboxylic Acid
Organotin (IV) carboxylates with the general formulae R2Sn(Cl)L [R = Me (1), n-Bu (2), Ph (3)] and R3SnL [R = Me (4), Ph (5)] have been synthesized by the reaction of 4-piperidinecarboxylic acid (HL) with KOH and R2SnCl2 (R = Me, n-Bu, Ph)/R3SnCl (R = Me, Ph) in methanol under stirring conditions. T...
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| Format: | Article |
| Language: | English |
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Wiley
2014-01-01
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| Series: | Bioinorganic Chemistry and Applications |
| Online Access: | http://dx.doi.org/10.1155/2014/959203 |
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| author | Shabbir Hussain Saqib Ali Saira Shahzadi Saroj K. Sharma Kushal Qanungo Muhammad Shahid |
| author_facet | Shabbir Hussain Saqib Ali Saira Shahzadi Saroj K. Sharma Kushal Qanungo Muhammad Shahid |
| author_sort | Shabbir Hussain |
| collection | DOAJ |
| description | Organotin (IV) carboxylates with the general formulae R2Sn(Cl)L [R = Me (1), n-Bu (2), Ph (3)] and R3SnL [R = Me (4), Ph (5)] have been synthesized by the reaction of 4-piperidinecarboxylic acid (HL) with KOH and R2SnCl2 (R = Me, n-Bu, Ph)/R3SnCl (R = Me, Ph) in methanol under stirring conditions. The metal ligand binding site, structure, and stability of complexes have been verified by FT-IR, (1H, 13C) NMR, EI-MS technique, and semiempirical study. The FT-IR data indicate the bidentate chelating mode of the carboxylate ligand which is also confirmed by semiempirical study. In solution state, five and four coordinated geometry around tin was confirmed by NMR spectroscopy. The EI-MS data agreed well with the molecular structure of the complexes. Thermodynamic parameters and molecular descriptors were calculated by using semiempirical PM3 method. HOMO-LUMO calculations show that chlorodiorganotin complexes are more susceptible to nucleophilic attack as compared to triorganotin complexes. Computed negative heat of formation indicates that complexes 1–4 are thermodynamically stable. The organotin(IV) carboxylates displayed powerful antimicrobial activities against various strains of bacteria and fungi and their minimal inhibitory concentration were also evaluated. The complexes exhibited comparatively higher hemolytic activity as compared to free ligand. |
| format | Article |
| id | doaj-art-af6ed080e9804efeafd07c0c1c2a5dcb |
| institution | Kabale University |
| issn | 1565-3633 1687-479X |
| language | English |
| publishDate | 2014-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Bioinorganic Chemistry and Applications |
| spelling | doaj-art-af6ed080e9804efeafd07c0c1c2a5dcb2025-02-03T05:58:39ZengWileyBioinorganic Chemistry and Applications1565-36331687-479X2014-01-01201410.1155/2014/959203959203Synthesis, Characterization, Semiempirical and Biological Activities of Organotin(IV) Carboxylates with 4-Piperidinecarboxylic AcidShabbir Hussain0Saqib Ali1Saira Shahzadi2Saroj K. Sharma3Kushal Qanungo4Muhammad Shahid5Department of Chemistry, GC University, Faisalabad 38000, PakistanDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, PakistanDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, PakistanDepartment of Applied Sciences and Humanities, Faculty of Engineering and Technology, Mody Institute of Technology and Science, Deemed University, Lakshmangarh, Sikar, Rajasthan 332311, IndiaDepartment of Applied Sciences and Humanities, Faculty of Engineering and Technology, Mody Institute of Technology and Science, Deemed University, Lakshmangarh, Sikar, Rajasthan 332311, IndiaDepartment of Chemistry and Biochemistry, University of Agriculture, Faisalabad 38000, PakistanOrganotin (IV) carboxylates with the general formulae R2Sn(Cl)L [R = Me (1), n-Bu (2), Ph (3)] and R3SnL [R = Me (4), Ph (5)] have been synthesized by the reaction of 4-piperidinecarboxylic acid (HL) with KOH and R2SnCl2 (R = Me, n-Bu, Ph)/R3SnCl (R = Me, Ph) in methanol under stirring conditions. The metal ligand binding site, structure, and stability of complexes have been verified by FT-IR, (1H, 13C) NMR, EI-MS technique, and semiempirical study. The FT-IR data indicate the bidentate chelating mode of the carboxylate ligand which is also confirmed by semiempirical study. In solution state, five and four coordinated geometry around tin was confirmed by NMR spectroscopy. The EI-MS data agreed well with the molecular structure of the complexes. Thermodynamic parameters and molecular descriptors were calculated by using semiempirical PM3 method. HOMO-LUMO calculations show that chlorodiorganotin complexes are more susceptible to nucleophilic attack as compared to triorganotin complexes. Computed negative heat of formation indicates that complexes 1–4 are thermodynamically stable. The organotin(IV) carboxylates displayed powerful antimicrobial activities against various strains of bacteria and fungi and their minimal inhibitory concentration were also evaluated. The complexes exhibited comparatively higher hemolytic activity as compared to free ligand.http://dx.doi.org/10.1155/2014/959203 |
| spellingShingle | Shabbir Hussain Saqib Ali Saira Shahzadi Saroj K. Sharma Kushal Qanungo Muhammad Shahid Synthesis, Characterization, Semiempirical and Biological Activities of Organotin(IV) Carboxylates with 4-Piperidinecarboxylic Acid Bioinorganic Chemistry and Applications |
| title | Synthesis, Characterization, Semiempirical and Biological Activities of Organotin(IV) Carboxylates with 4-Piperidinecarboxylic Acid |
| title_full | Synthesis, Characterization, Semiempirical and Biological Activities of Organotin(IV) Carboxylates with 4-Piperidinecarboxylic Acid |
| title_fullStr | Synthesis, Characterization, Semiempirical and Biological Activities of Organotin(IV) Carboxylates with 4-Piperidinecarboxylic Acid |
| title_full_unstemmed | Synthesis, Characterization, Semiempirical and Biological Activities of Organotin(IV) Carboxylates with 4-Piperidinecarboxylic Acid |
| title_short | Synthesis, Characterization, Semiempirical and Biological Activities of Organotin(IV) Carboxylates with 4-Piperidinecarboxylic Acid |
| title_sort | synthesis characterization semiempirical and biological activities of organotin iv carboxylates with 4 piperidinecarboxylic acid |
| url | http://dx.doi.org/10.1155/2014/959203 |
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