Hydrogen-halide versus alkyl-halide oxidative addition in dimethyl platinum(II) complexes: Crystal structure of [PtBr2(bpy)]

Momeni, Badri Z.; Hamzeh, Saeideh; Hosseini, Simin S.; Röminger, Frank

doi:10.1016/j.ica.2007.01.011

Cited by 30 publications

(21 citation statements)

References 25 publications

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“…As shown in Table 2, the average Pt-N distance is 2.02 Å and Pt-Br distance is 2.44 Å, while the N-Pt-N and Br-Pt-Br angles are 89.9°and 92.2°, respectively, all of these agreeing well with the data of similar platinum complexes described in the literatures. [29][30][31] The six-membered chelate ring formed with the Pt(II) atom adopts the boat conformation and the imidazole ring is nearly parallel to the Pt(II) coordination plane. The complex molecules are linked by molecular interactions involving the bromine atoms and the hydrogen atoms in the OH, NH 2 and NH groups (Fig.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Characterization and Cytotoxicity of Dihalogeno-platinum(II) Complexes with L-Histidine Ligand

Xie

Liu

et al. 2009

CHEMICAL & PHARMACEUTICAL BULLETIN

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Diiodo-, dibromo-and dichloro-platinum(II) complexes containing L-histidine ligand were prepared. Their spectra and X-ray crystal structure of the dibromo-platinum(II) complex were described. Only the dichloro-platinum(II) complex showed comparable cytotoxic activity with carboplatin against A549/ATCC, HT-29, and LNcap cell lines. Nevertheless the complexes with COOH-substituted ligands histidine may be good starting materials to synthesize targeting platinum complexes since they could be easily linked to suitable carrier molecules via esterification.

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Section: Resultsmentioning

confidence: 99%

Synthesis, Characterization and Cytotoxicity of Dihalogeno-platinum(II) Complexes with L-Histidine Ligand

Xie

Liu

et al. 2009

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Only a few reactions were reported in which the cis products [16,17] or even mixtures of cis and trans oxidative addition product were formed [18,19]. Due to the unexpected dependence of the diastereoselectivity on the oxidative addition of RI (MeI versus EtI), a broader variety of organyl halides was reacted with diacetylplatinum(II) complexes (3).…”

Section: Synthesismentioning

confidence: 99%

Reactivity of diacetylplatinum(II) complexes: oxidative addition of alkyl halides and crystal structures of acetyl platinum(IV) complexes

Werner

Bruhn

Steinborn

2008

Transition Met Chem

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Diacetylplatinum(II) complexes [Pt(COMe) 2 -(N^N)] (N^N = bpy, 3a; 4,4 0 -t-Bu 2 -bpy, 3b) were found to undergo oxidative addition reactions with organyl halides. The reaction of 3a with methyl iodide and propargyl bromide led to the formation of the cis addition products (OC-6-34)-[Pt(COMe) 2 (R)X(bpy)] (R = Me, X = I, 4a; CH 2 C:CH, X = Br, 4k). Analogous reactions of 3a with ethyl iodide, benzyl bromide, and substituted benzyl bromides, 3-(bromomethyl)pyridine, 2-(bromomethyl)thiophene, allyl bromide, and cyclohex-2-enyl bromide led to exclusive formation of the trans addition products (OC-6-43)-[Pt(COMe) 2 (R)X(bpy)] (X = I, R = Et, 4b; X = Br, R = CH 2 C 6 H 5 , 4c; CH 2 C 6 H 4 (o-Br), 4d; CH 2 C 6 H 4 (p-COOH), 4e; CH 2 -3-py (3-pyridylmethyl), 4f; CH 2 -2-tp (2-thiophenylmethyl), 4g; CH 2 CH=CH 2 , 4h; c-hex-2-enyl (cyclohex-2-enyl), 4i). All complexes 4 were characterized by microanalysis, 1 H and 13 C NMR and IR spectroscopy. Additionally, complexes 4a, 4f, and 4g were characterized by single-crystal X-ray diffraction analyses. Reactions of 3a and 3b with o-, m-and p-bis(bromomethyl)benzene, respectively, led to the formation of dinuclear platinum(IV) complexes [{Pt(COMe) 2 Br(N^N)} 2 {l-(CH 2 ) 2 C 6 H 4 }] (5). These complexes were characterized by microanalysis, IR spectroscopy, and depending on their solubility by 1 H and 13 C NMR spectroscopy, too. A single-crystal X-ray diffraction analysis of complex [{Pt(COMe) 2 Br(bpy)} 2 {l-m-(CH 2 ) 2 C 6 H 4 }] (5b) confirmed its dinuclear composition. The solid-state structures of 4a, 4f, 4g, and 5b are discussed in terms of C-HÁÁÁO and O-HÁÁÁO hydrogen bonds as well as p-p stacking between aromatic rings.

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“…These complexes have a long history and can be easily prepared by the oxidative addition of alkyl or aryl halides to platinum(II) complexes, respectively [1][2][3]. The oxidative addition has also been used as a useful method in the formation of oligomers, polymers and dendrimers [1].…”

Section: Introductionmentioning

confidence: 99%

“…The platinum(II) complex [PtMe 2 (bu 2 bpy)] (bu 2 bpy = 4,4 0 -di-tert-butyl-2,2 0 -bipyridine) (1) reacted with 1,2-dibromotetrachloroethane in a 2:1 mole ratio of Pt(II): (CBrCl 2 ) 2 to afford trans-[PtMe 2 BrCl(bu 2 bpy)] (2) and [PtCl 2 (bu 2 bpy)] (3). The 1 H NMR spectroscopy shows that the Pt-Me bond cleavage is mainly involved after a fast oxidative addition reaction.…”

Section: Introductionmentioning

confidence: 99%

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Unexpected formation of dihaloplatinum(II) and platinum(IV) complexes in the reaction of [PtMe2(bu2bpy)] with 1,2-dibromotetrachloroethane: Crystal structure of trans-[PtMe2BrCl(bu2bpy)]

Momeni

Hosseini

Röminger

2009

Inorganic Chemistry Communications

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Hydrogen-halide versus alkyl-halide oxidative addition in dimethyl platinum(II) complexes: Crystal structure of [PtBr2(bpy)]

Cited by 30 publications

References 25 publications

Synthesis, Characterization and Cytotoxicity of Dihalogeno-platinum(II) Complexes with L-Histidine Ligand

Synthesis, Characterization and Cytotoxicity of Dihalogeno-platinum(II) Complexes with L-Histidine Ligand

Reactivity of diacetylplatinum(II) complexes: oxidative addition of alkyl halides and crystal structures of acetyl platinum(IV) complexes

Unexpected formation of dihaloplatinum(II) and platinum(IV) complexes in the reaction of [PtMe2(bu2bpy)] with 1,2-dibromotetrachloroethane: Crystal structure of trans-[PtMe2BrCl(bu2bpy)]

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