title: Variable coordination and C-S bond cleavage activity of N-substituted imidazolidine-2-thiones towards copper: synthesis, spectroscopy, structures, ESI-mass and antimicrobial studies.
abstract: An equimolar reaction of copper(i) iodide with N-ethyl-imidazolidine-2-thione (l-Et) in acetonitrile formed black prismatic crystals over a period of three weeks. The X-ray structure determination of black crystals revealed that the thio-ligand l-Et has transformed into a new thio-ligand, 1-ethyl-3-(1-ethyl-4,5-dihydro-1H-imidazol-2-yl)imidazolidine-2-thione (l-NEt), through C-S rupture/C-N bond formation which was coordinated in the unusual 2D polymer, {(CuII(κ2-N,S-l-NEt)2)·(CuI4)·(CuI2)}n1. An ESR spectrum supported the presence of divalent CuIIin the polymer. In contrast, reaction of copper(i) iodide with N-phenyl-imidazolidine-2-thione (l-Ph) in 1 : 1 molar ratio yielded a polymer, [-Cu(μ-I)2Cu(μ-S-l-Ph)2Cu-]n2, with alternate Cu2I2and Cu2S2cores. Further, a series of reactions of copper(i) halides with N-substituted imidazolidine-2-thiones, namely, l-R in 1 : 2 metal to ligand molar ratio (M : L) in acetonitrile have yielded different type of complexes: trigonal planar {CuX(κ1-S-l-R)2, R, X : Et, I, 4; Me, I, 5; Bun, I,6; Me, Br,7; Bun, Br, 8; Me, Cl, 9; Prn, Cl, 10; Ph, Cl, 11}, dinuclear [Cu2Br2(μ-S-l-Ph)2(κ1-S-l-Ph)2] 12, tetranuclear, [Cu4I2(μ-I)2(μ-S-l-Ph)4(κ1-S-l-Ph)2] 3 and hexanuclear [Cu6Cl6(μ-S-l-Bun)6] 13. All these complexes have been characterized using analytical data, IR and proton NMR spectroscopy, ESI-mass studies and single crystal X-ray crystallography. The antimicrobial activity of these complexes has been investigated against Gram positive bacteria, namely, Staphylococcus aureus (MTCC740), methicillin resistant Staphylococcus aureus (MRSA), Gram negative bacteria, Klebsiella pneumoniae (MTCC109), Salmonella typhimurium (MTCC741) and Candida albicans (MTCC227)- a yeast. It is significant to add that among various complexes tested for cytotoxicity toward living cells, 4, 5, 8, 9 and 10 complexes were toxic, while complex 12 was non-toxic.
authors.affiliation: Department of Chemistry, Guru Nanak Dev University, Amritsar - 143 005, India. tarlokslobana@yahoo.co.in.
authors.forename: Jaspreet K
authors.initials: JK
authors.lastname: Aulakh
authors.affiliation: Department of Chemistry, Guru Nanak Dev University, Amritsar - 143 005, India. tarlokslobana@yahoo.co.in.
authors.forename: Tarlok S
authors.identifier: http://orcid.org/0000-0002-5658-6317
authors.initials: TS
authors.lastname: Lobana
authors.affiliation: Department of Microbiology, Guru Nanak Dev University, Amritsar-143 005, India.
authors.forename: Henna
authors.initials: H
authors.lastname: Sood
authors.affiliation: Department of Microbiology, Guru Nanak Dev University, Amritsar-143 005, India.
authors.forename: Daljit S
authors.initials: DS
authors.lastname: Arora
authors.affiliation: Departamento de Quimica Inorganica, Facultad de Farmacia, Universidad de Santiago, 15782-Santiago, Spain.
authors.forename: Isabel
authors.identifier: http://orcid.org/0000-0001-6779-0359
authors.initials: I
authors.lastname: Garcia-Santos
authors.affiliation: Department of Chemistry, Guru Nanak Dev University, Amritsar - 143 005, India. tarlokslobana@yahoo.co.in.
authors.forename: Geeta
authors.initials: G
authors.lastname: Hundal
authors.affiliation: Department of Chemistry, Keene State College, Keene, NH 03435-2001, USA.
authors.forename: Manpreet
authors.initials: M
authors.lastname: Kaur
authors.affiliation: Department of Chemistry, Keene State College, Keene, NH 03435-2001, USA.
authors.forename: Victoria A
authors.initials: VA
authors.lastname: Smolenski
authors.affiliation: Department of Chemistry, Keene State College, Keene, NH 03435-2001, USA.
authors.forename: Jerry P
authors.initials: JP
authors.lastname: Jasinski
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D002244:Carbon / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic; D003300:Copper / Q000737:chemistry*; D005031:Ethylenethiourea / Q000737:chemistry*; D009584:Nitrogen / Q000737:chemistry; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D021241:Spectrometry, Mass, Electrospray Ionization; D013057:Spectrum Analysis; D013455:Sulfur / Q000737:chemistry
chemical_list: D000890:Anti-Infective Agents; D009942:Organometallic Compounds; D005031:Ethylenethiourea; D013455:Sulfur; D002244:Carbon; D003300:Copper; D009584:Nitrogen