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Synthesis, Characterization, and Bioactivity of Schiff Bases and Their Cd2+, Zn2+, Cu2+, and Ni2+ Complexes Derived from Chloroacetophenone Isomers with S-Benzyldithiocarbazate and the X-Ray Crystal Structure of S-Benzyl-β-N-(4-chlorophenyl)methylenedithiocarbazate

Two bidentate Schiff base ligands having nitrogen sulphur donor sequence were derived from the condensation of S-benzyldithiocarbazate (SBDTC) with 2-chloroacetophenone and 4-chloroacetophenone to give S-benzyl-β-N-(2- chlorophenyl)methylenedithiocarbazate (NS2) and S-benzyl-β-N-(4- chlorophenyl)met...

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Main Authors: Break, Mohammed Khaled, Mohamed Tahir, Mohamed Ibrahim, Crouse, Karen Anne, Khoo, Teng Jin
Format: Article
Language:English
English
Published: Hindawi Publishing Corporation 2013
Online Access:http://psasir.upm.edu.my/id/eprint/30261/1/Synthesis.pdf
http://psasir.upm.edu.my/id/eprint/30261/
http://www.hindawi.com/journals/bca/2013/362513/
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spelling my.upm.eprints.302612015-08-25T03:39:10Z http://psasir.upm.edu.my/id/eprint/30261/ Synthesis, Characterization, and Bioactivity of Schiff Bases and Their Cd2+, Zn2+, Cu2+, and Ni2+ Complexes Derived from Chloroacetophenone Isomers with S-Benzyldithiocarbazate and the X-Ray Crystal Structure of S-Benzyl-β-N-(4-chlorophenyl)methylenedithiocarbazate Break, Mohammed Khaled Mohamed Tahir, Mohamed Ibrahim Crouse, Karen Anne Khoo, Teng Jin Two bidentate Schiff base ligands having nitrogen sulphur donor sequence were derived from the condensation of S-benzyldithiocarbazate (SBDTC) with 2-chloroacetophenone and 4-chloroacetophenone to give S-benzyl-β-N-(2- chlorophenyl)methylenedithiocarbazate (NS2) and S-benzyl-β-N-(4- chlorophenyl)methylenedithiocarbazate (NS4) isomers. Each of the ligands was then chelated with Cd2+, Zn2+, Cu2+, and Ni2+. The compounds were characterized via IR spectroscopy and melting point while the structure of NS4 was revealed via X-ray crystallography. Finally, the compounds were screened for antimicrobial activity to investigate the effect that is brought by the introduction of the chlorine atom to the benzene ring. X-ray crystallographic analysis showed that the structure of NS4 is planar with a phenyl ring that is nearly perpendicular to the rest of the molecules. The qualitative antimicrobial assay results showed that NS4 and its complexes lacked antifungal activity while Gram-positive bacteria were generally inhibited more strongly than Gram-negative bacteria. Furthermore, NS4 metal complexes were inhibited more strongly than the ligand while the opposite was seen with NS2 ligand and its complexes due to the partial solubility in dimethyl sulfoxide (DMSO). It was concluded that generally NS2 derivatives have higher bioactivity than that of NS4 derivatives and that the Cd complexes of both ligands have pronounced activity specifically on K. rhizophila. Hindawi Publishing Corporation 2013 Article PeerReviewed application/pdf en http://psasir.upm.edu.my/id/eprint/30261/1/Synthesis.pdf Break, Mohammed Khaled and Mohamed Tahir, Mohamed Ibrahim and Crouse, Karen Anne and Khoo, Teng Jin (2013) Synthesis, Characterization, and Bioactivity of Schiff Bases and Their Cd2+, Zn2+, Cu2+, and Ni2+ Complexes Derived from Chloroacetophenone Isomers with S-Benzyldithiocarbazate and the X-Ray Crystal Structure of S-Benzyl-β-N-(4-chlorophenyl)methylenedithiocarbazate. Bioinorganic Chemistry and Applications, 2013. art. no. 362513. pp. 1-13. ISSN 1565-3633; ESSN: 1687-479X http://www.hindawi.com/journals/bca/2013/362513/ 10.1155/2013/362513 English
institution Universiti Putra Malaysia
building UPM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Putra Malaysia
content_source UPM Institutional Repository
url_provider http://psasir.upm.edu.my/
language English
English
description Two bidentate Schiff base ligands having nitrogen sulphur donor sequence were derived from the condensation of S-benzyldithiocarbazate (SBDTC) with 2-chloroacetophenone and 4-chloroacetophenone to give S-benzyl-β-N-(2- chlorophenyl)methylenedithiocarbazate (NS2) and S-benzyl-β-N-(4- chlorophenyl)methylenedithiocarbazate (NS4) isomers. Each of the ligands was then chelated with Cd2+, Zn2+, Cu2+, and Ni2+. The compounds were characterized via IR spectroscopy and melting point while the structure of NS4 was revealed via X-ray crystallography. Finally, the compounds were screened for antimicrobial activity to investigate the effect that is brought by the introduction of the chlorine atom to the benzene ring. X-ray crystallographic analysis showed that the structure of NS4 is planar with a phenyl ring that is nearly perpendicular to the rest of the molecules. The qualitative antimicrobial assay results showed that NS4 and its complexes lacked antifungal activity while Gram-positive bacteria were generally inhibited more strongly than Gram-negative bacteria. Furthermore, NS4 metal complexes were inhibited more strongly than the ligand while the opposite was seen with NS2 ligand and its complexes due to the partial solubility in dimethyl sulfoxide (DMSO). It was concluded that generally NS2 derivatives have higher bioactivity than that of NS4 derivatives and that the Cd complexes of both ligands have pronounced activity specifically on K. rhizophila.
format Article
author Break, Mohammed Khaled
Mohamed Tahir, Mohamed Ibrahim
Crouse, Karen Anne
Khoo, Teng Jin
spellingShingle Break, Mohammed Khaled
Mohamed Tahir, Mohamed Ibrahim
Crouse, Karen Anne
Khoo, Teng Jin
Synthesis, Characterization, and Bioactivity of Schiff Bases and Their Cd2+, Zn2+, Cu2+, and Ni2+ Complexes Derived from Chloroacetophenone Isomers with S-Benzyldithiocarbazate and the X-Ray Crystal Structure of S-Benzyl-β-N-(4-chlorophenyl)methylenedithiocarbazate
author_facet Break, Mohammed Khaled
Mohamed Tahir, Mohamed Ibrahim
Crouse, Karen Anne
Khoo, Teng Jin
author_sort Break, Mohammed Khaled
title Synthesis, Characterization, and Bioactivity of Schiff Bases and Their Cd2+, Zn2+, Cu2+, and Ni2+ Complexes Derived from Chloroacetophenone Isomers with S-Benzyldithiocarbazate and the X-Ray Crystal Structure of S-Benzyl-β-N-(4-chlorophenyl)methylenedithiocarbazate
title_short Synthesis, Characterization, and Bioactivity of Schiff Bases and Their Cd2+, Zn2+, Cu2+, and Ni2+ Complexes Derived from Chloroacetophenone Isomers with S-Benzyldithiocarbazate and the X-Ray Crystal Structure of S-Benzyl-β-N-(4-chlorophenyl)methylenedithiocarbazate
title_full Synthesis, Characterization, and Bioactivity of Schiff Bases and Their Cd2+, Zn2+, Cu2+, and Ni2+ Complexes Derived from Chloroacetophenone Isomers with S-Benzyldithiocarbazate and the X-Ray Crystal Structure of S-Benzyl-β-N-(4-chlorophenyl)methylenedithiocarbazate
title_fullStr Synthesis, Characterization, and Bioactivity of Schiff Bases and Their Cd2+, Zn2+, Cu2+, and Ni2+ Complexes Derived from Chloroacetophenone Isomers with S-Benzyldithiocarbazate and the X-Ray Crystal Structure of S-Benzyl-β-N-(4-chlorophenyl)methylenedithiocarbazate
title_full_unstemmed Synthesis, Characterization, and Bioactivity of Schiff Bases and Their Cd2+, Zn2+, Cu2+, and Ni2+ Complexes Derived from Chloroacetophenone Isomers with S-Benzyldithiocarbazate and the X-Ray Crystal Structure of S-Benzyl-β-N-(4-chlorophenyl)methylenedithiocarbazate
title_sort synthesis, characterization, and bioactivity of schiff bases and their cd2+, zn2+, cu2+, and ni2+ complexes derived from chloroacetophenone isomers with s-benzyldithiocarbazate and the x-ray crystal structure of s-benzyl-β-n-(4-chlorophenyl)methylenedithiocarbazate
publisher Hindawi Publishing Corporation
publishDate 2013
url http://psasir.upm.edu.my/id/eprint/30261/1/Synthesis.pdf
http://psasir.upm.edu.my/id/eprint/30261/
http://www.hindawi.com/journals/bca/2013/362513/
_version_ 1643830005449359360
score 13.23648

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