Synthesis and structural characterization of the [2,9-dimethyl-4,7-diaza-2,9-decanedithiolato]oxorhenium(V) complex

Chryssou, Katerina; Pelecanou, Maria; Papadopoulos, Minas; Raptopoulou, Catherine P.; Pirmettis, Ioannis; Chiotellis, E.; Stassinopoulou, C. I.

doi:10.1016/s0020-1693(97)05727-7

Cited by 10 publications

(7 citation statements)

References 23 publications

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“…In the complexes of this study, the displacement of Re site from the equatorial plane in the direction of the oxo group is approximately 0.666-0.692 Å as shown in Table 3. The sulfur distances are all fairly unexceptional ranging from 2.26 to 2.33 Å, well within the range of those previously reported [36][37][38]. Also, the Re-O alcohol distances range from 1.96 to 1.99 Å, while the Re-N imine distances range from 2.08 to 2.12 Å.…”

Section: Resultssupporting

confidence: 86%

Oxorhenium(V) complexes containing tridentate Schiff-base and monothiol coligands

Femia

Chen

Babich³

et al. 2000

Inorganica Chimica Acta

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The reaction of [n-(C(4)H(9))(4)N][ReOBr(4)(OPPh(3))] with the tridentate Schiff-base [HOC(6)H(4)C(H)NC(6)H(4)SH] allows for the isolation of [ReOBr{eta(3)-(OC(6)H(4)C(H)NC(6)H(4)S)}] (1). The reaction of [n-(C(4)H(9))(4)N][ReOBr(4)(OPPh(3))] with [HOC(6)H(4)C(H)NC(6)H(4)SH] and the appropriate benzenethiol (C(6)H(4)X-4-SH) where X=H, Br, Cl, F, and OCH(3) in methanol-acetonitrile treated with triethylamine has led to the isolation of a series of rhenium complexes of the type [ReO{eta(3)-(OC(6)H(4)C(H)NC(6)H(4)S)} (eta(1)-C(6)H(4)X-4-S)] (X=H (2), Br (3), Cl (4), F (5), and OCH(3) (6)). Likewise, under similar reaction conditions, the use of benzylmercaptan ligands of the type (C(6)H(4)X-4-CH(2)SH) where X=H, Cl, F, and OCH(3) has led to the isolation of a series of rhenium complexes of the type [ReO{eta(3)-(OC(6)H(4)C(H)NC(6)H(4)S)} (eta(1)-C(6)H(4)X-4-CH(2)S)] (X=H (7), Cl (8), F (9), and OCH(3) (10)). The incorporation of the appropriate amine functionality into the substituent R of the monodentate ligand allows for the isolation of a cationic oxorhenium(V) species, namely, [ReO{eta(3)-(OC(6)H(4)C(H)NC(6)H(4)S)} (eta(1)-C(5)H(4)NH-2-S)][Br] (11).

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Section: Resultssupporting

confidence: 86%

Oxorhenium(V) complexes containing tridentate Schiff-base and monothiol coligands

Femia

Chen

Babich³

et al. 2000

Inorganica Chimica Acta

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“…In the complexes of this study, the displacement of Re site from the equatorial plane in the direction of the monothiol group is approximately 0.0753-0.1087 Å as shown in Table 4. The Re-N amine distances range from 2.21 to 2.23 Å while the sulfur distances are all fairly unexceptional, ranging from 2.27 to 2.32 Å well within the range of those reported previously [52][53][54]. Tables 2 and 4 compare the relevant bond angles and lengths for compounds 1-7, 9 and 10, respectively.…”

Section: Resultssupporting

confidence: 70%

Synthesis and characterization of complexes of the {ReO}3+ core with SNS and S donor ligands

Femia

Chen

Maresca³

et al. 2000

Inorganica Chimica Acta

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The reaction of [ReOCl(3)(PPh(3))(2)] with N,N-bis(2-mercaptoethyl)benzylamine and 4-bromobenzenethiol allowed for the isolation of [ReO{eta(3)-(SCH(2)CH(2))(2)N(CH(2)C(6)H(5))}-(eta(1)-C(6)H(4)Br-4-S)] (1). The reaction of [ReOCl(3)(PPh(3))(2)] with [(HSCH(2)CH(2))(2)N(CH(2)C(5)H(4)N)] and the appropriate thiol in chloroform treated with triethylamine has led to the isolation of a series of neutral rhenium complexes of the type [ReO{eta(3)-(SCH(2)CH(2))(2)N(CH(2)C(5)H(4)N)}(eta(1)-C(6)H(4)X-4-S)] (X = Br (2), Cl (3), F (4), and OCH(3) (5)) and [ReO{eta(3)-(SCH(2)CH(2))(2)N(CH(2)C(5)H(4)N)}(eta(1)-C(6)H(4)OCH(3)-4-CH(2)S)] (6). Likewise, under similar reaction conditions, the use of the related tridentate ligand, [(HSCH(2)CH(2))(2)N(CH(2)CH(2)C(5)H(4)N)], has led to the isolation of a series of rhenium complexes of the type [ReO{eta(3)-(SCH(2)CH(2))(2)N(CH(2)CH(2)C(5)H(4)N)}(eta(1)-C(6)H(4)X-4-S)] (X=Br (7), Cl (8), OCH(3) (9)), as well as [ReO{eta(3)-(SCH(2)CH(2))(2)N(CH(2)CH(2)C(5)H(4)N)}(eta(1)-C(6)H(4)Cl-4-CH(2)S)].0.5CH(3)(CH(2))(4)CH(3) (10). These compounds are extensions of the '3+1' approach to the synthesis of materials with the {MO}(3+) core (M=Tc and Re), which have applications in nuclear medicine. The ligands chosen allow systematic exploration of the consequences of para-substitution on the monodentate thiolate ligand [S] and of derivatization of the substituent R on the tridentate aminodithiol ligand [SNS] of the type (HSCH(2)CH(2))(2)NR. Such modifications can influence lipophilicity, charge, size and molecular weight of the complex and consequently the biodistribution.

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“…The protonated nitrogen atom of the ligand (N2) and the oxo group occupy the axial positions of the distorted octahedron. The RedO bond lengths are in the range observed in analogous complexes 21,22,25,35 The coordination geometry about rhenium in 5b is distorted square pyramidal with the SNN donor atom set of the ligand and the aromatic thiol defining the equatorial plane and the doubly bonded oxygen in the apex. The metal lies 0.70 Å out of the equatorial plane toward the oxo group.…”

Section: Resultsmentioning

confidence: 74%

“…24 The presence of the substituent (COCH 2 R) and the simulataneous reduction of the CdO moiety on the nitrogen appear to be important in the preservation of the diazolidine ring because in its absence the LiAlH 4 reduction leads only to the open chain ligand. 25 Complex 2a. The ability of 1 to act as tetradentate ligand around the ReO(V) core and generate complexes 2 of the ReO[SNN(R)S] type, analogous to those obtained with the TcO(V) core, 6 was demonstrated with ligand 1a.…”

Section: Resultsmentioning

confidence: 99%

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New Oxorhenium(V) Complexes from the Widely Used Diaminedithiol (DADT) Ligand System

et al. 2002

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Synthesis of the 2,9-dimethyl-4,7-diaza-4-alkyl-2,9-decanedithiol (1, alkyl = morpholinylethyl in a, and alkyl = pyrrolidinylethyl in b), following a widely used synthetic scheme for diaminedithiol (DADT) ligands, led to the isolation of 1-alkyl-2-(1'-methyl-1'-sulfanylethyl)-3-(2' '-methyl-2' '-sulfanylpropyl)diazolidine (3) as the major product. Both ligands 1 and 2 gave complexes with the oxorhenium ReO(V) core. Ligand 1 gave the expected ReO[SNNS] complex (2) with the side chain on nitrogen in the syn configuration. Ligand 3 gave, in the presence of a monodentate aromatic thiol, complexes of the ReO[SNN][S][S] (4) and ReO[SNN][S] type (5), respectively, in which the diazolidine ring has rearranged to a thiazolidine ring. Crystallographic analysis showed that in 4 the coordination geometry about the metal is distorted octahedral where the equatorial plane is defined by the sulfur and one of the nitrogen atoms of the ligand and the two sulfurs of the aromatic thiols, while the axial positions are occupied by the oxygen of the ReO core and the second nitrogen of the ligand. Specifically, complex 4a crystallizes in space group P2(1)/c, a = 15.63(1) A, b = 15.28(2) A, c = 16.07(1) A, beta = 113.78(2) degrees, V = 3512(5) A(3), Z = 4. Complex 4b crystallizes in space group P2(1)/n, a = 14.560(9) A, b = 14.804(9) A, c = 19.85(1) A, beta = 90.94(2) degrees, V = 4278(1) A(3), Z = 4. In 5b, the coordination geometry is distorted square pyramidal with the SNN donor atom of the ligand and the aromatic thiol defining the equatorial plane and the doubly bonded oxygen occupying the apex of the pyramid. Complex 5b crystallizes in space group P(-)1, a = 9.387(5) A, b = 11.306(5) A, c = 14.040(6) A, alpha = 84.51(1) degrees, beta = 84.45(2) degrees, gamma = 87.17(1) degrees, V = 1475(1) A(3), Z = 2. All isolated complexes are neutral and lipophilic. Complete assignments of (1)H and (13)C NMR resonances are reported.

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Synthesis and structural characterization of the [2,9-dimethyl-4,7-diaza-2,9-decanedithiolato]oxorhenium(V) complex

Cited by 10 publications

References 23 publications

Oxorhenium(V) complexes containing tridentate Schiff-base and monothiol coligands

Oxorhenium(V) complexes containing tridentate Schiff-base and monothiol coligands

Synthesis and characterization of complexes of the {ReO}3+ core with SNS and S donor ligands

New Oxorhenium(V) Complexes from the Widely Used Diaminedithiol (DADT) Ligand System

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