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Synthesis, Characterization, Semiempirical and Biological Activities of Organotin(IV) Carboxylates with 4-Piperidinecarboxylic Acid

Organotin (IV) carboxylates with the general formulae R(2)Sn(Cl)L [R = Me (1), n-Bu (2), Ph (3)] and R(3)SnL [R = Me (4), Ph (5)] have been synthesized by the reaction of 4-piperidinecarboxylic acid (HL) with KOH and R(2)SnCl(2) (R = Me, n-Bu, Ph)/R(3)SnCl (R = Me, Ph) in methanol under stirring con...

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Autores principales: Hussain, Shabbir, Ali, Saqib, Shahzadi, Saira, Sharma, Saroj K., Qanungo, Kushal, Shahid, Muhammad
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Hindawi Publishing Corporation 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4274932/
https://www.ncbi.nlm.nih.gov/pubmed/25548551
http://dx.doi.org/10.1155/2014/959203
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author Hussain, Shabbir
Ali, Saqib
Shahzadi, Saira
Sharma, Saroj K.
Qanungo, Kushal
Shahid, Muhammad
author_facet Hussain, Shabbir
Ali, Saqib
Shahzadi, Saira
Sharma, Saroj K.
Qanungo, Kushal
Shahid, Muhammad
author_sort Hussain, Shabbir
collection PubMed
description Organotin (IV) carboxylates with the general formulae R(2)Sn(Cl)L [R = Me (1), n-Bu (2), Ph (3)] and R(3)SnL [R = Me (4), Ph (5)] have been synthesized by the reaction of 4-piperidinecarboxylic acid (HL) with KOH and R(2)SnCl(2) (R = Me, n-Bu, Ph)/R(3)SnCl (R = Me, Ph) in methanol under stirring conditions. The metal ligand binding site, structure, and stability of complexes have been verified by FT-IR, ((1)H, (13)C) 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.
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spelling pubmed-42749322014-12-29 Synthesis, Characterization, Semiempirical and Biological Activities of Organotin(IV) Carboxylates with 4-Piperidinecarboxylic Acid Hussain, Shabbir Ali, Saqib Shahzadi, Saira Sharma, Saroj K. Qanungo, Kushal Shahid, Muhammad Bioinorg Chem Appl Research Article Organotin (IV) carboxylates with the general formulae R(2)Sn(Cl)L [R = Me (1), n-Bu (2), Ph (3)] and R(3)SnL [R = Me (4), Ph (5)] have been synthesized by the reaction of 4-piperidinecarboxylic acid (HL) with KOH and R(2)SnCl(2) (R = Me, n-Bu, Ph)/R(3)SnCl (R = Me, Ph) in methanol under stirring conditions. The metal ligand binding site, structure, and stability of complexes have been verified by FT-IR, ((1)H, (13)C) 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. Hindawi Publishing Corporation 2014 2014-10-13 /pmc/articles/PMC4274932/ /pubmed/25548551 http://dx.doi.org/10.1155/2014/959203 Text en Copyright © 2014 Shabbir Hussain et al. https://creativecommons.org/licenses/by/3.0/ This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Research Article
Hussain, Shabbir
Ali, Saqib
Shahzadi, Saira
Sharma, Saroj K.
Qanungo, Kushal
Shahid, Muhammad
Synthesis, Characterization, Semiempirical and Biological Activities of Organotin(IV) Carboxylates with 4-Piperidinecarboxylic Acid
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
topic Research Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4274932/
https://www.ncbi.nlm.nih.gov/pubmed/25548551
http://dx.doi.org/10.1155/2014/959203
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