Crystal structures of two ammine-glycine derivatives of divalent platinum: Cis-dichloroammineglycineplatinum (II) [PtNH3 (NH2CH2COOH)-Cl2] and cis-chloroammineglycinatoplatinum (II) [PtNH3 (NH2CH2COO)Cl]

Байдина, И. А.; Podberezskaya, N. V.; Krylova, L. F.; Борисов, С. В.; Bakakin, V. V.

doi:10.1007/bf00754173

Cited by 3 publications

(4 citation statements)

References 3 publications

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“…In the metallacycles, the angles around the Pd centers in both 11 and 13 are within the 78.73(9)–79.36(8)° range, being slightly smaller than those previously observed in the mononuclear palladium and platinum five-membered chelates [Pd(phen){ C (O)NPhC(O) N Ph}] (80.14 Å), [PdI{ C NC 6 H 3 (2,6-Me 2 )}{ C (C 6 H 4 (2- N H 2 ))NC 6 H 3 (2,6-Me 2 )}] (82.89 Å), ci s-[PtCl(NH 3 )( N H 2 CH 2 CO O )] (81.56 Å), and [PtCl(PPh 3 )( N Me 2 CH 2 NMe 2 C H 2 )](Cl) (82.30 Å) …”

Section: Resultsmentioning

confidence: 63%

“…[PdI{Ct NC 6 H 3 (2,6-Me 2 )}{C(C 6 H 4 (2-NH 2 ))dNC 6 H 3 (2,6-Me 2 )}](82.89 Å),55 cis-[PtCl(NH 3 )(NH 2 CH 2 COO)] (81.56 Å),56 and [PtCl(PPh 3 )(NMe 2 CH 2 NMe 2 CH 2 )](Cl) (82.30 Å) 57. Among the PdÀC distances, Pd1ÀC6 (in 11) and Pd1ÀC3 (in 13) [1.988(2) Å] are slightly longer than (while Pd2ÀC24 1.977(2) Å for 11 and Pd2ÀC4 1.975(2) Å for 13 are equal to) those reported for the relevant palladium complexes cis-[PdCl 2 -{C(OMe)dN(H)Me} 2 ] (1.953À1.972 Å)48 and cis-[PdCl 2 {C-(dNHCy)NHNHC(dNHCy)} 2 ] (1.958À1.964 Å) 49.…”

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confidence: 99%

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Novel Reactivity Mode of Metal Diaminocarbenes: Palladium(II)-Mediated Coupling between Acyclic Diaminocarbenes and Isonitriles Leading to Dinuclear Species

Tskhovrebov¹,

Luzyanin²,

Dolgushin³

et al. 2011

Organometallics

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Metal-mediated coupling between equimolar amounts of cis-[PdCl2(CNR1)2] [R1 = 2,6-Me2C6H3 (Xyl) 1, 2-Cl,6-Me-C6H3 2, cyclohexyl (Cy) 3] and H2NC5H3R2N [R2 = H, 2-aminopyridine 4; R2 = NH2, 2,6-diaminopyridine 5] proceeds smoothly for 12 h at 20–25 °C and leads to the diaminocarbene species [PdCl{C(NHC5H3R2 N)N(H)R1}(CNR1)]Cl (6–9). In the reaction of 2 with 5 (1:1 molar ratio), corresponding carbene 10 was detected only by high-resolution ESI+-MS in a mixture with other yet unidentified products. Addition of each of 6–8 to starting 1 or 2 (1:1 molar ratio) in the presence of excess solid K2CO3 in CHCl3 and heating of the reaction mixture for 12 h at 40 °C led to a novel type of dinuclear complexes, 11 (75% isolated yield) and 13 (65%). Similar dinuclear complexes 12 and 14, formed by addition of 7 or 10 to 2, were identified by high-resolution ESI+-MS in the mixture with other species (e.g., 7 and 10). Generation of 11–14 proceeds via a cascade reaction including addition of the amino group of a 2-aminopyridine to the metal-activated isonitrile, ring-closure, and coupling of the derived acyclic diaminocarbene complex with the yet unreacted starting material. Complexes 6–9, 11, and 13 were fully characterized by elemental analyses (C, H, N), high-resolution ESI+-MS, IR, and 1H and 13C{1H} NMR spectroscopies, while 10, 12, and 14 were identified by ESI+-MS. In addition, the structures of five complexes [6, 6a (the latter is a neutral species derived from the deprotonation of 6), 9, 11, and 13] were elucidated by single-crystal X-ray diffraction.

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Section: Resultsmentioning

confidence: 63%

mentioning

confidence: 99%

Novel Reactivity Mode of Metal Diaminocarbenes: Palladium(II)-Mediated Coupling between Acyclic Diaminocarbenes and Isonitriles Leading to Dinuclear Species

Tskhovrebov¹,

Luzyanin²,

Dolgushin³

et al. 2011

Organometallics

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“…The unreacted isonitrile is in the trans position to the carbene carbon atom of { C (NC(C 6 R 1 R 2 R 3 R 4 CO N ))N(H)R}, which acts as a bidentate ligand, forming the five-membered chelate ring. In the metallacycle, the angles N(1)−Pd(1)−C(9) and N(1)−Pt(1)−C(9) are 77.55(18)° and 78.09(10)°, being slightly smaller than that previously observed in the related palladium and platinum five-membered chelates [Pd(phen){ C (O)NPhC(O) N Ph}] (80.14 Å), [PdI{ C NC 6 H 3 (2,6-Me 2 )}{ C (C 6 H 4 (2- N H 2 ))NC 6 H 3 (2,6-Me 2 )}] (82.89 Å), ci s-[PtCl(NH 3 )( N H 2 CH 2 CO O )] (81.56 Å), or [PtCl(PPh 3 )( N Me 2 CH 2 NMe 2 C H 2 )](Cl) (82.30 Å) . The carbene ligands in both 10 and 27 are in the E -configuration, and the Pd−C carbene [Pd(1)−C(9) 2.001(3) Å] distance in 10 is slightly longer, while the Pt−C carbene [Pt(1)−C(9) 2.002(5) Å] in 27 is equal within 3σ to those reported for the related palladium and platinum carbene complexes cis -[PdCl 2 { C (OMe)N(H)Me} 2 ] (1.953−1.972 Å), cis -[PdCl 2 { C (NHCy)NHNH C (NHCy)} 2 ] (1.958−1.964 Å), [Pt{η 2 -( S , S ′)-S 2 CC(C(O)Me)}(CNBu t ){C(NEt 2 )(NHBu t )}] [2.053(2) Å], and cis -[PtCl 2 { C NC 6 H 3 (2,6-Me 2 )}{ C (NH 2 )N(H)C 6 H 3 (2,6-Me 2 )}] [1.983(7) Å] .…”

Section: Resultsmentioning

confidence: 64%

“…The latter ligand forms a five-membered metallacycle, with the N(1)−Pt(1)−C(9) angle [78.2(2)°] slightly smaller than in previously characterized relevant platinum five-membered chelates, e.g. [PtCl 2 (2,2′-bpy)] (79.06−80.80 Å), ci s-[PtCl(NH 3 )( N H 2 CH 2 CO O )] (81.56 Å), or [PtCl( N Me 2 CH 2 NMe 2 C H 2 )(PPh 3 )](Cl) (82.30 Å) . The carbene ligand is in the Z -configuration, and both Pt−C carbene [Pt(1)−C(9) 1.999(6) Å] and C carbene −N [C(9)−N(3) 1.322(7) Å] distances are in good agreement with those previously observed in the related platinum carbene complexes [PtCl{ C NC 6 H 3 (2,6-Me 2 )}{ C (NH 2 )N(H)C 6 H 3 (2,6-Me 2 )}(Ph 2 CNH)](Cl) [1.995(6) and 1.330(8) Å] and [PtCl 2 { C NC 6 H 3 (2,6-Me 2 )}{ C (NH 2 )N(H)C 6 H 3 (2,6-Me 2 )}] [1.983(7) and 1.295(8) Å] .…”

Section: Resultsmentioning

confidence: 98%

Coupling between 3-Iminoisoindolin-1-ones and Complexed Isonitriles as a Metal-Mediated Route to a Novel Type of Palladium and Platinum Iminocarbene Species

et al. 2008

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The reaction between isonitrile in cis-[MCl2(CNR)2] [M = Pd, R = Cy 1, Bu t 2, C6H3(2,6-Me2) 3; M = Pt, R = Cy 4, Bu t 5, C6H3(2,6-Me2) 6] and various unsubstituted or substituted iminoisoindolin-1-ones HNCC6R1R2R3R4CONH [R1−R4 = H 7; R1, R3, R4 = H, R2 = Me/R1, R2, R4 = H, R3 = Me 8 (isomeric mixture); R1, R4 = H, R2, R3 = Cl 9] proceeds under reflux conditions in CHCl3 for 2 h. The subsequent workup provides complexes [MCl{C(NC(C6R1R2R3R4CON))N(H)R}(CNR)] (M = Pd, 10−18; M = Pt, 19−27), bearing a novel type of carbene ligands, which were isolated in good (80−85% for the PdII complexes) to moderate (60−65% for the PtII species) yields. The addition of the iminoisoindolin-1-one to isonitriles is metal-mediated and has a general character. The reaction of cis-[PtCl2(CNC6H4OMe-4)2] (28) with 7 affords a mixture of PtII-containing species including the monoadduct [PtCl{C(NC(C6H4CON))N(H)C6H4OMe-4}(CNC6H4OMe-4)] (29), the unusual binuclear compound [Pt2{C(NC(C6H4CON))N(H)C6H4OMe-4}2(CNC6H4OMe-4)2(μ-HNCC6H4CON)](Cl) (30) with a bridging monodeprotonated 3-iminoisoindolin-1-one, and [Pt(C6H4CONCNH){C(NC(C6H4CON))N(H)C6H4OMe-4}(CNC6H4OMe-4)] (31), the latter resulting from the replacement of the chloro ligand in 29 by the deprotonated iminoisoindolin-1-one. Complexes 10−27 were characterized by elemental analyses (C, H, N), ESI+-MS, IR, and 1D (1H, 13C{1H}) and 2D (1H,1H-COSY, 1H,13C-HMQC/1H,13C-HSQC, 1H,13C-HMBC) NMR spectroscopies, while 29−31 by ESI+-MS, IR, and 1H NMR. In addition, the structures of three carbene complexes (10, 27, and 30) were elucidated by single-crystal X-ray diffraction analysis.

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Three new platinum(II)—dipeptide complexes

Shi

Hambley

Freeman

1999

Journal of Inorganic Biochemistry

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Crystal structures of two ammine-glycine derivatives of divalent platinum: Cis-dichloroammineglycineplatinum (II) [PtNH3 (NH2CH2COOH)-Cl2] and cis-chloroammineglycinatoplatinum (II) [PtNH3 (NH2CH2COO)Cl]

Cited by 3 publications

References 3 publications

Novel Reactivity Mode of Metal Diaminocarbenes: Palladium(II)-Mediated Coupling between Acyclic Diaminocarbenes and Isonitriles Leading to Dinuclear Species

Novel Reactivity Mode of Metal Diaminocarbenes: Palladium(II)-Mediated Coupling between Acyclic Diaminocarbenes and Isonitriles Leading to Dinuclear Species

Coupling between 3-Iminoisoindolin-1-ones and Complexed Isonitriles as a Metal-Mediated Route to a Novel Type of Palladium and Platinum Iminocarbene Species

Three new platinum(II)—dipeptide complexes

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