Dithiocarbamate Complexes of Platinum Group Metals: Structural Aspects and Applications
Abstract
:1. Introduction
2. Methods
3. Results
3.1. Solid-State Structures
3.1.1. Ruthenium
3.1.2. Rhodium
3.1.3. Palladium
3.1.4. Osmium
3.1.5. Iridium
3.1.6. Platinum
3.2. Nuclear Magnetic Resonance (NMR) Studies
3.2.1. 1H NMR
- (i)
- Decrease down a Group,
- (ii)
- Increase across a Period,
- (iii)
- Increase with the oxidation state of the metal ion.
Barrier to C–N Bond Rotation
3.2.2. 13C NMR
3.2.3. 195Pt NMR
3.3. Applications
3.3.1. Biological Applications
Complex a | IC50/μM b | Ref. | |||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
LU | MCF7 | Heap-1c1c7 | PC-3 | MDA-MB-231 | HepG2/CTR | HepG2/SB3 | HeLa | HL60 | Daudi | LoVo | A549 | HTB-81 | MRC-5 | ||
β-[Ru2(L57)5]Cl | - | - | - | - | - | 0.62(0.08) | 0.59(0.01) | 0.45(0.02) | - | - | - | - | - | - | [180] |
β-[Ru2(L63)5]Cl | - | - | - | - | - | 0.66(0.01) | 0.75(0.02) | 0.46(0.04) | - | - | - | - | - | - | [180] |
β-[Ru2(L60)5]Cl | - | - | - | - | - | 9.2(2) | >10 | 3.95(0.07) | - | - | - | - | - | - | [180] |
β-[Ru2(L61)5]Cl | - | - | - | - | - | 1.28(0.05) | 0.90(0.02) | 0.27(0.01) | - | - | - | - | - | - | [180] |
[PPh3Ru(η1-ClL)(CO)(L57)] | - | - | - | - | ≈25 | - | - | - | - | - | - | - | - | - | [56] |
[PPh2(p-tolyl)Pd(L69)Cl] | 25.03(6.4) | 26.9(4.1) | 22.6(3.0) | 18.4(2.8) | 19.4(1.1) | - | - | - | - | - | - | - | - | - | [110] |
3.72 | 6.20 | 5.46 | [109] | ||||||||||||
[P(p-tolyl)3Pd(L69)Cl] | 32.9(1.8) | 25.2(0.1) | 36.9(5.1) | 38.4(1.2) | 29.5(2.0) | - | - | - | - | - | - | - | - | - | [110] |
5.18 | 5.29 | 5.76 | [109] | ||||||||||||
[PPh2(p-tolyl)Pd(L76)Cl] | 5.6(0.4) | 0.01(0.005) | 0.1(0.2) | 1.3(2.2) | 2.8(1.2) | - | - | - | - | - | - | - | - | - | [110] |
[P(p-tolyl)3Pd(L76)Cl] | 2.9(0.1) | 2.21(3.5) | 12.2(1.9) | 15.0(3.9) | 7.1(1.9) | - | - | - | - | - | - | - | - | - | [110] |
[PPh2(p-tolyl)Pd(L78)Cl] | 10.57(2.4) | 2.4(1.0) | 10(3) | 33.6(2.9) | 5.4(4.1) | - | - | - | - | - | - | - | - | - | [110] |
[P(p-tolyl)3Pd(L78)Cl] | 10(2.4) | 3.02(0.3) | 2.8(0.4) | 3.9(0.024) | 7.0(3.6) | - | - | - | - | - | - | - | - | - | [110] |
[PPh2(p-tolyl)Pd(L67)Cl] | - | 4.51 | - | 5.11 | - | - | - | - | - | - | - | 4.83 | - | - | [109] |
[P(p-tolyl)3Pd(L67)Cl] | - | 4.12 | - | 7.12 | - | - | - | - | - | - | - | 7.21 | - | - | [109] |
[PPh2(CH2Ph)Pd(L24)Cl] | - | - | - | - | - | - | - | - | - | - | - | - | 3.67 | - | [114] |
[PPh2(tert-But)Pd(L31)Cl] | - | - | - | - | - | - | - | - | - | - | - | - | 9.52 | - | [115] |
[PPh2(CH2Ph)Pd(L28)Cl] | - | - | - | - | - | - | - | - | - | - | - | - | 4.57 | - | [115] |
[PPh2(Cl)Pd(L28)Cl] | - | - | - | - | - | - | - | - | - | - | - | - | 21.7 | - | [115] |
[PPh3Pd(L26)Cl] | - | - | - | - | - | - | - | - | - | - | - | - | 2.12 | - | [115] |
[PPh2(tert-But)Pd(L38)Cl] | - | - | - | - | - | - | - | - | - | - | - | - | - | 36.7(2.9) | [117] |
[PPh2(nPr)Pd(L26)Cl] | - | - | - | - | - | - | - | - | - | - | - | - | - | >100 | [117] |
[PPh3Pd(L36)Cl] | - | - | - | - | - | - | - | - | - | - | - | - | - | 71.5(13.1) | [117] |
[PPh3Pd(L35)Cl] | - | - | - | - | - | - | - | - | - | - | - | - | - | >100 | [117] |
[PPh3Pd(L37)Cl] | - | - | - | - | - | - | - | - | - | - | - | - | - | 81.6(13.1) | [117] |
[PPh2(p-tolyl)Pd(L36)Cl] | - | - | - | - | - | - | - | - | - | - | - | - | - | 22.8(2.4) | [117] |
[PPh2(p-tolyl)Pd(L35)Cl] | - | - | - | - | - | - | - | - | - | - | - | - | - | >100 | [117] |
[PPh2(p-tolyl)Pd(L38)Cl] | - | - | - | - | - | - | - | - | - | - | - | - | - | 30.8(2.6) | [117] |
[PPh2(CH2Ph)Pd(L38)Cl] | - | - | - | - | - | - | - | - | - | - | - | - | - | >100 | [117] |
[PPh3Pd(L38)Cl] | - | - | - | - | - | - | - | - | - | - | - | - | - | 65.3(12.5) | [117] |
[Pd(3-pic)(L20)Cl] | - | - | - | - | - | - | - | >100 | >100 | >100 | >100 | - | - | - | [198] |
[Pd(2-pic)(L20)Cl] | - | - | - | - | - | - | - | 69.54(0.31) | 59.62(0.54) | 97.12(1.93) | 53.24(1.52) | - | - | - | [198] |
[Pt(3-pic)(L20)Cl] | - | - | - | - | - | - | - | 98.90(2.33) | >100 | >100 | >100 | - | - | - | [198] |
[Pt(2-pic)(L20)Cl] | - | - | - | - | - | - | - | 9.32(1.22) | 39.12(1.33) | 45.22(1.21) | 25.32(2.02) | - | - | - | [198] |
3.3.2. Other Applications
4. Conclusions
Author Contributions
Funding
Conflicts of Interest
Abbreviations
bmi | 1-benzyl-3-methyl-imidazole |
bpy | 2,2′-bipyridine |
btfmppy | 2-(2,4-bis(trifluoromethyl)-phenyl)pyridine |
buppy | 2-(4′-tert-butylphenyl)pyridine) |
bzq | benzo(h)quinoline |
C≡CBMIDA | C≡CB(O2CCH2)2NMe |
cyclam | 1,4,8,11-tetraazacyclotetradecane |
depe | 1,2-bis(diethylphosphino)ethane |
dmbp | 4,4′-dimethyl-2,2′-bipyridine |
dmso | dimethylsulfoxide |
dpci | 3, 4-diphenylcinnoline |
dpp | 4,6-diphenyl pyrimidine |
dppb | 1,4-bis(diphenylphosphino)butane |
dppe | 1,2-bis(diphenylphosphino)ethane |
dppf | 1,1′-bis(diphenylphosphino)ferrocene |
dppm | 1,1-bis(diphenylphosphino)methane |
dppp | 1,3-bis(diphenylphosphino)propane |
fcdpm | 5-Ferrocenyl dipyrromethene |
mtz | 5-methyltetrazole |
pba | 4-(2-pyridyl)benzaldehyde |
pbt | 2-phenylbenzothiazole |
p-cymene | 1-isopropyl-4-methylbenzene |
phpy | 2-phenylpyridine |
phpz | n-phenylpyrazole |
pmea | 2-metallated 3-perylmethylen-4′-ethylaniline |
ppy | 2-phenylpyridine |
pqz | 4-phenylquinazoline |
ptbt | 2-(p-tolyl)benzothiazole |
pyr | pyrimidine |
tfmbpy | 2′,6′-bis(trifluoromethyl)-2,4′-bipyridine |
tfmpiq | 1-(4-(trifluoromethyl)phenyl)-isoquinoline |
tfmppy | 2-(4-(trifluoromethyl)phenyl)pyridine |
tfmpqz | 4-(4-(trifluoromethyl)phenyl)quinazoline |
tmeda | N,N,N′,N′-Tetramethylethane-1,2-diamine |
Tp* | HB(3,5-dimethylpyrazol-1-yl)3 |
tptz | 2,4,6-tris(2-pyridyl)pyrazine-N,N′,N″ |
X | 3-(((4-chlorophenyl)imino)methyl)-2-hydroxy-5-methylphenyl |
X1 | η3, η3–2,7-dimethylocta-1,6-dien-3,8-diyl |
X2 | 1,2-bis(2-phenylethynylmethylene)cyclohexane |
X3 | |
X4 | 2,5-di-p-tolyl-1,3,4-oxadiazole |
X5 | 3-perylenylmethylen-4′-ethylaniline |
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−S2CNRR′ | ||
---|---|---|
Ligand | R | R′ |
L1 | H | H |
L2 | H | Me |
L3 | H | Et |
L4 | H | Ph |
L5 | H | p-tolyl |
L6 | H | C6H4Et-p |
L7 | H | C6H4Cl-p |
L8 | Me | Me |
L9 | Me | CH2C≡CH |
L10 | Me | CH2CH=CH2 |
L11 | Me | n-Bu |
L12 | Me | n-Hex |
L13 | Me | CH2Ph |
L14 | Me | Ph |
L15 | Me | Cy |
L16 | Me | CH2CH(OMe)2 |
L17 | Me | CH2COO− |
L18 | Me | CH2COOH |
L19 | Me | CH2COOMe |
L20 | Me | CH2COOEt |
L21 | Me | CH2COO-t-Bu |
L22 | Me | CH2CH2OC(=O)CH=CHCOOEt |
L23 | Me | 2-methyl-1,3-dioxolane |
L24 | Et | Et |
L25 | Et | CH2CH2OH |
L26 | CH2CH2OMe | CH2CH2OMe |
L27 | CH2CH=CH2 | CH2CH=CH2 |
L28 | n-Pr | n-Pr |
L29 | i-Pr | i-Pr |
L30 | (CH2)3NMe2 | (CH2)3NMe2 |
L31 | n-Bu | n-Bu |
L32 | n-Bu | CH2Ph |
L33 | n-Bu | Ph |
L34 | CH2(i-Pr) | CH2(i-Pr) |
L35 | n-Hex | n-Hex |
L36 | n-Dec | n-Dec |
L37 | CH2CH(Me)(Et) | CH2CH(Me)(Et) |
L38 | CH2CH(Et)(n-Bu) | CH2CH(Et)(n-Bu) |
L39 | CH2Ph | CH2Ph |
L40 | CH2Ph | CH2C6H4OMe-3 |
L41 | CH2Ph | CH2C5H4N-3 |
L42 | CH2Ph | CH2C4H3NMe |
L43 | CH2Ph | CH2C5H4FeCp |
L44 | (CH2)2PPh2 | (CH2)2PPh2 |
L45 | C5H4N-2 | C5H4N-2 |
L46 | Ph | Ph |
L47 | Cy | Cy |
L48 | p-tolyl | p-tolyl |
L49 | C6H4CF3-p | C6H4CF3-p |
L50 | C6H4(t-Bu)-p | C6H4(t-Bu)-p |
L51 | CH2COO− | CH2COO− |
L52 | CH2COOH | CH2COOH |
L53 | CH2COOH | CH2COO− |
L54 | CH2C4H3O | CH2C4H3O |
L55 | CH2C6H4OH-o | p-tolyl |
L56 | CH2C(=O)N(H)(CH2)3CH3 | CH2C(=O)N(H)(CH2)3CH3 |
Crystal | Formulation | REFCODE | Donor Set | Ref. |
---|---|---|---|---|
1 | Ru(L8)3 | OCOVUZ | S6 | [25] |
2 | Ru(L20)3 | OCOWEK | S6 | [25] |
3 | [Ru(L57)3], CHCl3 | OCOWAG | S6 | [25] |
4 | [Ru2(L8)5]BF4, CHCl3, CH3CN | REDCEK | S6 | [32] |
5 | [Ru2(L8)5]{[Mo6O19]0.5}, CH3COCH3 | YUJFOZ | S6 | [33] |
6 | Ru(L8)2((CH3)2SO)2 | REDBUZ | cis-O2S4 | [32] |
7 | Ru(L57)2((CH3)2SO)2 | REDCAG | cis-O2S4 | [32] |
8 | (dppb)Ru(L24)2 | EBESOW | cis-P2S4 | [34] |
9 | [(dppb)Ru(L63)2], CH2Cl2 | PAZWOD | cis-P2S4 | [35] |
10 | (dppb)Ru(L79)2 | EBESIQ | cis-P2S4 | [34] |
11 | [Ru(bpy)2(L8)]PF6, 0.75((CH3CH2)2O) | DANDOM | N4S2 | [36] |
12 | [Ru(bpy)2(L56)]PF6 | WOHLAH | N4S2 | [37] |
13 | [Ru(cyclam)(L24)]BPh4, 0.16(CH2Cl2) | BUPMEF | N4S2 | [38] |
14 | [(dppm)2Ru(L9)]PF6, 0.5(CH2Cl2) | COZMIP | P4S2 | [39] |
15 | [(dppm)2Ru(L26)]PF6 | HUYPAT | P4S2 | [40] |
16 | {[(dppm)2Ru]2(L74)}[BF4]2, 3(CHCl3) | QAVHAX | P4S2 | [41] |
17 | [(dppm)2Ru(L74)Pd(PPh3)2][BF4]2, 3(CH2Cl2), (CH3CH2)2O | QONVAR | P4S2 | [42] |
18 | (PPh3)2Ru(L8)Cl2, 2(CH2Cl2) | HUPMAH | Cl2P2S2 | [43] |
19 | (PPh3)2Ru(L24)Cl2, CH2Cl2 | GUVPIX | Cl2P2S2 | [44] |
20 | (PPh3)2Ru(L29)Cl2, CH2Cl2 | GUVPOD | Cl2P2S2 | [44] |
21 | [(PPh3)Ru(tptz)(L24)]Cl, 2.5(H2O) | ABIBET | N3PS2 | [45] |
22 | (PEt3)Ru(L8)2(CO) | PEBZUS | CPS4 | [46] |
23 | (PPh3)Ru{Ge(p-tolyl)2}(L8)2(CO), CH2Cl2 | VEKKIH | CGePS3 | [47] |
24 | (PPh3)Ru(κ2(Si,N)-SiPh2NHC5H4N)(L8)(CO) | RADNIU | CNPS2Si | [48] |
25 | (PPh3)Ru(κ2(Si,N)-SiPh2OC5H4N)(L8)(CO), 2.5(C6H6) | RADNEQ | CNPS2Si | [48] |
26 | (PPh3)Ru(κ2(Si,O)-SiPh2OCCH3O)(L8)(CO), CH2Cl2 | RADNOA | CNPS2Si | [48] |
27 | Ru(B(NCH2PPh2)2C6H4)(L24)(CO) | UNAVEM | BCP2S2 | [49] |
28 | (PPh3)2Ru(H)(L7)(CO), 0.5(CH3(CH2)4CH3) | OWOKER | CHP2S2 | [50] |
29 | (PPh3)2Ru(H)(L8)(CO) | RADMUF | CHP2S2 | [48] |
30 | (PPh3)2Ru(H)(L84)(CO) | YOSJEX | CHP2S2 | [51] |
31 | (PPh3)2Ru(Si(Cl)Ph2)(L8)(CO) | RADNAM | CP2S2Si | [48] |
32 | (PPh3)2Ru(Ge(p-tolyl)3)(L24)(CO), 1.19(CH2Cl2) | VEKKAZ | CGeP2S2 | [47] |
33 | (PPh3)2Ru(C(H)=C(H)BMIDA)(L24)(CO), CH3COCH3 | HUDPON | C2P2S2 | [52] |
34 | (PPh3)2Ru(C(H)=C(H)C6H4Me-4)(L10)(CO), CH2Cl2 | COZMEL | C2P2S2 | [39] |
35 | (PPh3)2Ru(C(H)=C(H)C6H4Me-4)(L26)(CO), 0.3(CH2Cl2) | HUYPEX | C2P2S2 | [40] |
36 | (PPh3)2Ru(C(H)=C(H)C6H4Me-4)(L27)(CO), CH2Cl2 | OJEYIM | C2P2S2 | [53] |
37 | (PPh3)2Ru(C(H)=C(H)pyrenyl-1)(L84)(CO), 1.5(CH2Cl2) | YOSJIB | C2P2S2 | [51] |
38 | (PPh3)2Ru(C(C≡C(Ph)=C(H)Ph)(L84)(CO) | YOSJOH | C2P2S2 | [51] |
39 | (PPh3)2Ru(C(C≡CSiMe3)=C(H)SiMe3)(L8)(CO), unknown solvate | KOQPEO | C2P2S2 | [54] |
40 | [(PPh3)2Ru(C(C≡CPh)=C(H)Ph)(L65)(CO)]Cl, 1.25(CH2CH2OH) | DOZHOQ | C2P2S2 | [55] |
41 | (PPh3)2Ru(C≡CBMIDA)(L8)(CO) | HUDPAZ | C2P2S2 | [52] |
42 | (PPh3)2Ru(C≡CBMIDA)(L24)(CO), 0.5(CH2Cl2), unknown solvate | HUDPED | C2P2S2 | [52] |
43 | (PPh3)2Ru(X)(L24)(CO) | BOHTOK | C2P2S2 | [56] |
44 | (PPh3)2Ru(L24)(CO)Cl, 2.5(C6H6) | HUDQAA | CClP2S2 | [52] |
45 | (PPh3)2Ru(L24)(CO)Cl, CH2Cl2 | HUDQEE | CClP2S2 | [52] |
46 | (PPh3)2Ru(L24)(CO)Cl, 2(CHCl3), unknown solvate | HUDQII | CClP2S2 | [52] |
47 | (PPh3)2Ru(L24)(CO)Cl, CH3OH | HUDQOO | CClP2S2 | [52] |
48 | (PPh3)Ru(Ge(p-tolyl)3)(L24)(CO)2 | VEKKED | C2GePS2 | [47] |
49 | Ru(L22)(CO)3Cl | ROQQUM | fac-C3ClS2 | [57] |
50 | CpRu(PPh3)(L11) | YEDMEA | C3PS2 | [58] |
51 | CpRu(PPh3)(L24) | KEZVOB | C3PS2 | [59] |
52 | CpRu(PPh3)(L28) | YEDMAW | C3PS2 | [58] |
53 | CpRu(PPh3)(L57) | BUYQIW | C3PS2 | [60] |
54 | {[CpRu(L24)]2(dppf)}, CH2Cl2 | IZIBAU | C3PS2 | [61] |
55 | CpRu(L8)(CO) | QIWNES | C4S2 | [62] |
56 | [Cp*Ru(L8)2][N(S=PPh2)2], 0.5(H2O) | PARVUA | C3S4 | [63] |
57 | [Cp*Ru(L8)(L24)]Cl, 2CHCl3 | TEYTEX | C3S4 | [64] |
58 | Cp*Ru(L8)Cl2 | WEYTUQ | C3Cl2S2 | [65] |
59 | Cp*Ru(L24)Cl2 | TEYSUM | C3Cl2S2 | [64] |
60 | Cp*Ru(S2C=O)(L8) | TEYTIB | C3S4 | [64] |
61 | Cp*Ru(S2C=O)(L24) | TEYTOH | C3S4 | [64] |
62 | [Cp*Ru(PPh3)(L8)Cl]Cl, 0.5(H2O), 1.5(CH3CN) | TEYTUN | C3ClPS2 | [64] |
63 | [Cp*Ru(PMe3)(L8)Cl]BPh4 | TEYVAV | C3ClPS2 | [64] |
64 | [Cp*Ru(L8)Cl]2[SbCl6]2 | WEYVEC | C3Cl2S2 | [65] |
65 | [Cp*Ru(L8)(CH3CN)2][PF6]2, 2CH3CN | WEYVAY | C3N2S2 | [65] |
66 | Cp*Ru(L8)(CO) | TEYVID | C4S2 | [64] |
67 | [(PPh3)2Ru(C(NMe2)OC(NMe2)=S)(L8)]ClO4 | HUPMEL | CP2S3 | [43] |
68 | [(PPh3)2Ru(C(NMe2)SC(NMe2)=S)(L8)]ClO4, 2(CH2Cl2) | HUPLUA | CP2S3 | [43] |
69 | Ru(X1)(L8)Cl | IQUFEG | C4ClS2 | [66] |
70 | Ru(X1)(L29)Cl | IQUFIK | C4ClS2 | [66] |
71 | [Ru(X1)(L8)(CH3CN)]PF6 | IQUFOQ | C4NS2 | [66] |
72 | (p-cymene)Ru(L79)Cl | PEKVIN | C3ClS2 | [67] |
Crystal | Formulation | REFCODE | Donor Set | Ref. |
---|---|---|---|---|
73 | Tp*Rh(η2-L24)(η1-L24) | BILHIO | N3S3 | [68] |
74 | [Rh(H){κ3-P,Si,P′-SiPh(NCH2PPh2)2C6H4}(L24)], 0.5(C6H6) | WODHOO | HP2S2Si | [69] |
75 | Rh(phpy)2(L24) | EMOKAU | C2N2S2 | [70] |
76 | Rh(phpy)2(L66) | XOCFUS | C2N2S2 | [71] |
77 | (PMe3)2Rh(X2)(L24) | KUPVOH | C2P2S2 | [72] |
Crystal | Formulation | REFCODE | Donor Set | Ref. |
---|---|---|---|---|
78 | Pd(L4)2 | YIRSIE | S4 | [73] |
79 | Pd(L8)2 | OMUJEN01 * | S4 | [74,75,76] |
80 | Pd(L11)2 | ODOYAI | S4 | [77] |
81 | Pd(L13)2 | LIGSAW | S4 | [78] |
82 | Pd(L15)2 | ZOJVAX | S4 | [79] |
83 | Pd(L16)2 | FUHXEN | S4 | [80] |
84 | Pd(L24)2 | DETCPD02 | S4 | [81] |
85 | Pd(L25)2 | FEVCER | S4 | [82] |
86 | Pd(L30)2 | QOWXUW | S4 | [83] |
87 | Pd(L33)2 | EMOKOI | S4 | [84] |
88 | Pd(L35)2 | ZOJTUP | S4 | [79] |
89 | Pd(L39)2 | LIGSEA | S4 | [78] |
90 | Pd(L39)2, C5H5N | ZOJTID | S4 | [79] |
91 | Pd(L39)2, 2Cr(C6H6)2, 2(C60) | CEBCES | S4 | [85] |
92 | Pd(L41)2 | HOMXEO | S4 | [86] |
93 | Pd(L42)2 | LUKTES | S4 | [87] |
94 | Pd(L47)2, C5H5N | ZOJTOJ | S4 | [79] |
95 | Pd(L57)2 | UBIFUI | S4 | [88] |
96 | Pd(L63)2 | XAZZOO | S4 | [89] |
97 | Pd(L64)2 | JESJUN | S4 | [90] |
98 | [Pd(L66)2], 3H2O | BEZKAU | S4 | [91] |
99 | Pd2(L86)2 | KENYIN | S4 | [92] |
100 | Pd2(L86)2, CHCl3 | KENYOT | S4 | [92] |
101 | Pd2(L87)2, 2(CH3OH) | IXIWAN | S4 | [93] |
102 | [Pd2(L44)2]Cl2, 1.5(CH3OH), 2(H2O) | IGUBAP | P2S2 | [94] |
103 | (fcdpm)Pd(L24) | YEFVOW | N2S2 | [95] |
104 | (fcdpm)Pd(L29) | YEFVUC | N2S2 | [95] |
105 | (fcdpm)Pd(L43) | VIZJOF | N2S2 | [96] |
106 | [Pd(dmbp)(L75)][PF6]2 | XEDWOV | N2S2 | [97] |
107 | [Pd(bpy)(L75)][PF6]2, CH3CN | XEDWUB | N2S2 | [97] |
108 | [(dppe)Pd(L57)]Cl, 1.33(H2O), CHCl3 | DIFQIU | P2S2 | [26] |
109 | [(dppp)Pd(L24)]BF4, 2(CHCl3) | WUMQEB | P2S2 | [98] |
110 | [(dppf)Pd(L57)]PF6, CH2Cl2 | DOZKOV | P2S2 | [99] |
111 | {[(PPh3)2Pd]2(L74)}[PF6]2, (CH3CH2)2O | KEKKAP | P2S2 | [100] |
112 | {[(PPh3)2Pd]2(L74)}[PF6]2, (CH3CH2)2O | KEKKET | P2S2 | [100] |
113 | {[(PPh3)2Pd]2(L85)}[PF6]2, (CH3CH2)2O | KEKKIX | P2S2 | [100] |
114 | {[(dppf)Pd]2(L74)}[BF4]2, 2.6(CH2Cl2) | RUDLEI | P2S2 | [101] |
115 | {[(dppf)Pd]2(L85)}[PF6]2, CH2Cl2, CH3CH2OH | ISEWIN | P2S2 | [102] |
116 | (PPh3)Pd(L31)Cl | RASYAN | ClPS2 | [103] |
117 | (PPh3)Pd(L32)Cl | NAJVEC | ClPS2 | [104] |
118 | (PPh3)Pd(L47)Cl | KIJROL | ClPS2 | [105] |
119 | (PPh3)Pd(L57)Cl, 0.5(CHCl3) | DICXOE | ClPS2 | [26] |
120 | (PPh3)Pd(L64)Cl | SAYZOI | ClPS2 | [106] |
121 | (PPh3)Pd(L68)Cl, 0.5(CHCl3) | NAJNOE | ClPS2 | [104] |
122 | (PPh3)Pd(L81)Cl | BULBAM | ClPS2 | [107] |
123 | [P(o-tolyl)3]Pd(L81)Cl | BUKZUD * | ClPS2 | [107,108] |
124 | [P(p-tolyl)3]Pd(L39)Cl | VANWAL | ClPS2 | [109] |
125 | [P(p-tolyl)3]Pd(L69)Cl | ROHJUW | ClPS2 | [110] |
126 | [P(p-tolyl)3]Pd(L71)Cl, CHCl3 | UNOYAZ | ClPS2 | [111] |
127 | [P(p-tolyl)3]Pd(L76)Cl | ROHKAD | ClPS2 | [110] |
128 | [P(C6H4Cl-p)3]Pd(L69)Cl | ADUHAL | ClPS2 | [112] |
129 | [P(C6H4Cl-p)3]Pd(L72)Cl | MEHHIT | ClPS2 | [113] |
130 | [P(C6H4Cl-p)3]Pd(L77)Cl | QEKTAE | ClPS2 | [114] |
131 | [P(C6H4F-p)]Pd(L69)Cl | ADUGOY | ClPS2 | [112] |
132 | [P(C6H4F-p)]Pd(L71)Cl | ADUGUE | ClPS2 | [112] |
133 | [P(C6H4F-p)]Pd(L72)Cl | MEHHEP | ClPS2 | [113] |
134 | [P(C6H4F-p)]Pd(L77)Cl} 0.5(CH3COCH3) | QEKSUX | ClPS2 | [114] |
135 | [PPh2(o-tolyl)]Pd(L71)Cl | GIQGUK | ClPS2 | [115] |
136 | [PPh2(p-tolyl)]Pd(L31)Cl | RASYER | ClPS2 | [103] |
137 | [PPh2(p-tolyl)]Pd(L39)Cl | VANVUE | ClPS2 | [109] |
138 | [PPh2(p-tolyl)]Pd(L67)Cl | VANVOY | ClPS2 | [109] |
139 | [PPh2(p-tolyl)]Pd(L69)Cl | ROHJOQ | ClPS2 | [110] |
140 | [PPh2(p-tolyl)]Pd(L71)Cl | UNOYON | ClPS2 | [111] |
141 | [PPh2(C6H4OMe-o)]Pd(L24)Cl, H2O | RAFLER | ClPS2 | [116] |
142 | [PPh2(nPr)]Pd(L26)Cl | EHOBOU | ClPS2 | [117] |
143 | [PPh2(tBu)]Pd(L38)Cl | EHOBUA | ClPS2 | [117] |
144 | [PPh2(CH2Ph)]Pd(L8)Cl | RAFLAN | ClPS2 | [116] |
145 | [PPh2(CH2Ph)]Pd(L24)Cl | GIQHAR | ClPS2 | [115] |
146 | [(PPh3)Pd(L68)(SCN)], 0.5(CH2Cl2) | NAJNIY | PS3 | [104] |
147 | [tBu(Ph)POH][tBu(Ph)P(=O)]Pd(L24) | SAGBIM | P2S2 | [118] |
148 | Cu{[tBu(PhP)(O)]Pd(L24)}2 | SAFZUV | P2S2 | [118] |
149 | Pd(phpz)(L24) | UMEBEU | CNS2 | [119] |
150 | Pd(phpy)(L63) | JUPNIT | CNS2 | [120] |
151 | Pd(C^N)(L24) | OVEPOV | CNS2 | [121] |
152 | Pd(X3)(L24), CH3(CH2)4CH3, 0.5(CH2Cl2) | FOHYEH | CNS2 | [122] |
153 | Pd(κ2-C,N-CH2SiPh2(CH2NC5H10))(L24) | EZEXIQ | CNS2 | [123] |
154 | (PPh3)Pd(pyr)(L57) | UQANEG | CPS2 | [124] |
155 | Pd(η3-C4H7)(L8) | ODOXOV | C2S2 | [77] |
156 | Pd(η3-C4H7)(L28) | ODOYEM | C2S2 | [77] |
Crystal | Formulation | REFCODE | Donor Set | Ref. |
---|---|---|---|---|
157 | Os(L8)2(CO)2 | KAZHIE | C2S4 | [130] |
158 | (PPh3)2Os(SiCl3)(L8)(CO), 2(CH2Cl2) | NEKGOA | CP2S2Si | [125] |
159 | (PPh3)2Os(SiMeCl2)(L8)(CO), 2(CH2Cl2) | NEKGIU | CP2S2Si | [125] |
160 | (PPh3)2Os(SiMe2Cl)(L8)(CO), CH2Cl2 | FIXRAG | CP2S2Si | [126] |
161 | (PPh3)2Os(SiMe2OH)(L8)(CO), x(CH3(CH2)5CH3) | FIXREK | CP2S2Si | [126] |
162 | (PPh3)2Os(SiMe2OSiMe3)(L8)(CO) | FIXROU | CP2S2Si | [126] |
163 | (PPh3)2Os(SiOH3)(L8)(CO) | FIXRIO | CP2S2Si | [126] |
164 | (PPh3)2Os(SnCl3)(L8)(CO), CHCl3 | QEWPAK | CP2S2Sn | [127] |
165 | (PPh3)2Os(SnF3)(L8)(CO), 2(CH2Cl2) | QEWPEO | CP2S2Sn | [127] |
166 | (PPh3)2Os(SnH3)(L8)(CO), C6H6 | QEWNUC | CP2S2Sn | [127] |
167 | (PPh3)2Os(SnHMe2)(L8)(CO), C6H6 | QEWPUE | CP2S2Sn | [127] |
168 | (PPh3)2Os(SnMeF2)(L8)(CO), CH2Cl2 | QEWPOY | CP2S2Sn | [127] |
169 | (PPh3)2Os(SnMe2Cl)(L8)(CO), C6H6 | TAXYOH | CP2S2Sn | [128] |
170 | (PPh3)2Os(SnMe2SnPh3)(L8)(CO), 2(CH2Cl2) | PENLIE | CP2S2Sn | [129] |
171 | (PPh3)Os(SnMe2C6H4PPh2)(L8)(CO) | TAXYUN | CP2S2Sn | [128] |
172 | (PPh3)Os(SnMeClC6H4PPh2)(L8)(CO) | TAXZAU | CP2S2Sn | [128] |
173 | Os3(L8)2(CO)10 | KUJFED | C3OsS2 | [131] |
174 | [Os4(L8)2(CO)12(CO2)(S)], 2(CH2Cl2) | KUJFIH | C3OS2, C3S3 | [131] |
175 | Os3(H)(L8)(CO)9 | KUJFUT | C3Os2S/C3HOs2S | [131] |
176 | Os3(H)(L24)(CO)9 | SATGUQ | C3Os2S/C3HOs2S | [132] |
Crystal | Formulation | REFCODE | Donor Set | Ref. |
---|---|---|---|---|
177 | Ir(ppy)2(L24) | WIHPUZ | C2N2S2 | [133] |
178 | Ir(buppy)2(L24) | MADKAE | C2N2S2 | [134] |
179 | Ir(pba)2(L24) | QOFTEN | C2N2S2 | [135] |
180 | Ir(tfmppy)2(L29) | FODDUA | C2N2S2 | [136] |
181 | Ir(btfmppy)2(L29) | FODDOU | C2N2S2 | [136] |
182 | Ir(tfmbpy)2(L29) | FODFAI | C2N2S2 | [136] |
183 | Ir(tfmpiq)2(L29) | HOFCUD | C2N2S2 | [137] |
184 | Ir(tfmpiq)2(L46), unknown solvate | HOFDAK | C2N2S2 | [137] |
185 | Ir(tfmpiq)2(L83), unknown solvate | HOFDEO | C2N2S2 | [137] |
186 | Ir(pqz)2(L82) | ZUQLUU | C2N2S2 | [27] |
187 | Ir(tfmpqz)2(L29) | LIYWUO | C2N2S2 | [138] |
188 | Ir(tfmpqz)2(L46) | CUMGUP | C2N2S2 | [139] |
189 | Ir(tfmpqz)2(L48) | CUMGOJ | C2N2S2 | [139] |
190 | Ir(tfmpqz)2(L49) | CUMHOK | C2N2S2 | [139] |
191 | Ir(tfmpqz)2(L50) | VIWDAJ | C2N2S2 | [140] |
192 | Ir(tfmpqz)2(L82) | LIYWOI | C2N2S2 | [138] |
193 | Ir(tfmpqz)2(L83) | VIWCUC | C2N2S2 | [140] |
194 | Ir(dpp)2(L24), CH2Cl2, unknown solvate | IQAFEN | C2N2S2 | [141] |
195 | Ir(dpci)2(L82), CH2Cl2, 1.5(H2O) | VITHEN | C2N2S2 | [142] |
196 | Ir(pbt)2(L24) | IXOJEM * | C2N2S2 | [143,144] |
197 | Ir(ptbt)2(L24) | WOTQUU | C2N2S2 | [145] |
198 | Ir(X4)2(L24), 0.5(H2O) | WEKROU * | C2N2S2 | [146,147] |
199 | (PPh3)2Ir(C5H5SMe)(L24) | ANOKAQ | C2P2S2 | [148] |
200 | [(PPh3)2Ir(C5H4SMe)(L24)]PF6 | ANOJUJ | C2P2S2 | [148] |
201 | [(PPh3)2Ir(C5H3Me-3SMe)(L24)]PF6, ClCH2CH2Cl | ANOKEU | C2P2S2 | [148] |
202 | [(PPh3)2Ir(C5H3OEt-3SMe)(L24)]PF6 | ANOKIY | C2P2S2 | [148] |
203 | [Cp*Ir(L24)(CO)]CF3SO3 | GEVGUK | C4S2 | [149] |
204 | [Cp*Ir(L24)]2[ClO4]2 | WIHNIL | C3S3 | [150] |
205 | Cp*Ir(mtz)(L8), 5-methyltetrazole | NOJPUY | C3NS2 | [151] |
206 | [{Cp*Ir(L8)}2(mtz)]PF6 | NOJQAF | C3NS2 | [151] |
207 | Cp*Ir(SH)(PMe3)(L5), CH2Cl2 | SIKPUY | C3PS2 | [152] |
208 | Cp*Ir(H)(PMe3)(L5) | SIKQEJ | C3HPS | [152] |
209 | [Cp*Ir(PPh3)(L24)]3[Cp*Ir(PPh3)(L25)(NCH3)][I]4 | OYUJEY | C3NPS | [153] |
Crystal | Formulation | REFCODE | Donor Set | Ref. |
---|---|---|---|---|
210 | Pt(L4)2 | YIRSOK | S4 | [73] |
211 | Pt(L6)2 | YIRXEF | S4 | [73] |
212 | Pt(L8)2 | TEDRIG * | S4 | [75,76] |
213 | Pt(L16)2 | FUHXIR | S4 | [80] |
214 | Pt(L27)2 | TUCMAH | S4 | [154] |
215 | Pt(L29)2 | LOWJEP | S4 | [155] |
216 | [Pt(L31)2], C60 | MOKNOR | S4 | [156] |
217 | Pt(L33)2 | EMOKUO | S4 | [84] |
218 | Pt(L34)2 | ZOJHUE | S4 | [155,157] |
219 | [Pt(L39)2], C6H5CN | ZOJJAM | S4 | [157] |
220 | Pt(L41)2 | LASPIH | S4 | [158] |
221 | Pt(L45)2 | UHOGIJ | S4 | [159] |
222 | Pt(L52)2 | MOHNUU | S4 | [160] |
223 | [Pt(L52)2], 6((CH3)2SO) | GUCQAZ | S4 | [161] |
224 | Pt(L54)2 | HOMXAK | S4 | [86] |
225 | Pt(L55)2, unknown solvate | GUMCEZ | S4 | [162] |
226 | Pt(L70)2 | WIFVUF | S4 | [163] |
227 | Pt(L80)2 | CAJWOC | S4 | [164] |
228 | Pt(L62)2 | GEZHEA | S3N | [165] |
229 | [Zn(H2O)4Pt(L17)2]n, 4(H2O) | GUCQED | S4 | [161] |
230 | [Zn(H2O)4Pt(L58)2]n, 2(H2O) | GUCQIH | S4 | [161] |
231 | {Zn(H2O)3Pt(L53)2]n, 3(H2O) | GUCQUT | S4 | [161] |
232 | {[Zn(H2O)4]2Pt(L51)2}n, 6(H2O) | GUCQON | S4 | [161] |
233 | [Pt(L57)Cl]5, 2(ClCH2CH2Cl) | HACCAR | ClS3 | [166] |
234 | (PPh3)Pt(η1-L57)(η2-L57), 2(CH2Cl2), 0.25(CH3(CH2)3CH3) | DIFQOA | PS3 | [26] |
235 | {[(PEt3)2Pt]2(L74)}(PF6)2, unknown solvate | RUDLAE | P2S2 | [101] |
236 | {[(PPh3)2Pt]2(L74)}(PF6)2 | RUDKUX | P2S2 | [101] |
237 | Pt(L57)(Cl)((CH3)2SO) | NASDAO | ClS3 | [167] |
238 | (PEt3)Pt(L24)Cl | TOWNUR | ClPS2 | [168] |
239 | (PPh3)Pt(L57)Cl, 0.5(CH2Cl2) | HACBUK | ClPS2 | [166] |
240 | [P(C6H4Cl-p)3]Pt(L73)Cl | AZIDAQ | ClPS2 | [169] |
241 | [P(C6H4F-p)3]Pt(L73)Cl | AZIDEU | ClPS2 | [169] |
242 | [P(C6H4F-p)3]Pt(L78)Cl | AZICUJ | ClPS2 | [169] |
243 | [P(p-tolyl)3]Pt(L76)Cl | RIZNEW | ClPS2 | [170] |
244 | Pt(bmi)(L24)I | AHADAR | CIS2 | [171] |
245 | Pt(bzq)(L8) | EQONOO | CNS2 | [172] |
246 | Pt(bzq)(L57) | EQONII | CNS2 | [172] |
247 | Pt(X5)(L24) | PUPHUF | CNS2 | [173] |
248 | [Pt(L24)]2(bpy), CH2Cl2 | RIZBUA | CNS2 | [174] |
249 | (PEt3)Pt(L24)(CH2(iPr)) | HUWGIR | CPS2 | [175] |
250 | Pt(PPh3)(L24)C≡W(CO)2(Tp*) | JUQRAR | CPS2 | [176] |
251 | Pt(bzq)(L8)(PPh2)2Pt(C6F5)2, 2(CH2Cl2) | QUFXAT | CNP2S2 | [177] |
252 | {Ag[Pt(bzq)(L57)]2}n, n(ClO4), n(CH3CN) | EQOPEG | AgCNS2 | [172] |
Metal Ion | Mean Shift, ppm | Sample Standard Deviation, ppm |
---|---|---|
Ru(II) | 3.20 | 0.50 |
Ru(III) | 3.63 | 0.37 |
Os(II) | 2.47 | 0.63 |
Rh(III) | 3.63 | 0.37 |
Ir(III) | 3.29 | 0.44 |
Pd(II) | 3.82 | 0.61 |
Pt(II) | 3.83 | 0.50 |
Pt(IV) | 3.51 | 0.26 |
Complex | δ, ppm | Ref. |
---|---|---|
[Ru(L8)3] | 28.85 | [25] |
28.70 | [32] | |
[Ru(L57)3] | 45.03, 36.28 | [25] |
44.40, 36.00 | [32] | |
[Ru(L19)3] | 26.80, 26.70, 21.83, 14.63 | [25] |
[Ru(L20)3] | 26.70, 26.23, 21.92, 14.55 | [25] |
[Ru(L21)3] | 26.82, 26.43, 21.32, 14.40 | [25] |
α-[Ru2(L8)5]Cl | 3.55, 3.52, 3.50, 3.20, 2.99 | [25] |
3.62, 3.46, 3.47, 3.17, 2.93 | [32] | |
β-[Ru2(L8)5]Cl | 3.55, 3.54, 3.51, 3.20, 3.19 | [32] |
α-[Ru2(L57)5]Cl | 4.05–3.37 | [25] |
4.25–3.15 | [32] | |
β-[Ru2(L57)5]Cl | 3.98–3.40 | [32] |
α-[Ru2(L19)5]Cl | 4.60–4.00, 3.48–3.14 | [25] |
β-[Ru2(L20)5]Cl | 5.14–4.45, 3.71–3.04 | [25] |
α-[Ru2(L21)5]Cl | 4.72–4.01, 3.64–2.62 | [25] |
Complex | ΔG, kJ mol−1 | ν(C–N), cm−1 | Ref. |
---|---|---|---|
[Ru(CO)2(L8)2] | 78 ± 1 | Not reported | [182] |
[Ru(CO)(PEt3)(L8)2] | 74 ± 1 and 71 ± 1 | Not reported | [46] |
[Os(CO)2(L8)2] | 74.2 ± 0.5 | Not reported | [130] |
[{PtMe3(L1)}2] | 71.43 ± 0.14 | 1609 | [178] |
[{PtMe3(L8)}2] | 81.54 ± 0.19 | 1530 | [178] |
[{PtMe3(L24)}2] | 82.89 ± 0.56 | 1516 | [178] |
[{PtMe3(L2)}2] | 72.27 ± 0.05 | 1517 | [178] |
[{PtMe3(L3}2] | 66.36 ± 0.05 | 1518 | [178] |
[{PtMe3(L4)}2] | 65.61 ± 0.01 | 1527 | [178] |
[{PtMe3(L14)}2] | 86.54 ± 0.29 87.24 ± 0.27 87.15 ± 0.35 | 1489 | [178] |
Complex | δ, ppm a | δ, ppm b | Ref. |
---|---|---|---|
[Pt(pbt)(L24)] | 686 | - | [143] |
[Pt(L18) 2] | 626 | - | [161] |
[Pt(L59)2] | 720 | - | [161] |
Zn[Pt(L58)2] | 793 | - | [161] |
[Pt(L52)2] | 603 | - | [161] |
Zn[Pt(L53)2] | 614 | - | [161] |
Zn2[Pt(L51)2] | 678 | - | [161] |
[WPt(μ-C)(L24)(CO)2(PPh3)(Tp*)] | 694 | - | [176] |
[Pt(pmea)(L24)] | 810 | - | [173] |
[PtMeI(pmea)(L24)] | 1333 | - | [173] |
[{PtMe3(L1)}2] | 1416 | - | [178] |
[{PtMe3(L8)}2] | 1577 | - | [178] |
[{PtMe3(L24)}2] | 1564 | - | [178] |
[{PtMe3(L2)}2] | 1623, 1609, 1598, 1587 | - | [178] |
[{PtMe3(L3}2] | 1626, 1609, 1607, 1596 | - | [178] |
[{PtMe3(L4}2] | 1632, 1600, 1587, 1582 | - | [178] |
[{PtMe3(L14)}2] | 1584, 1575, 1569, 1559 | 1601 | [178] |
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Tan, Y.S.; Yeo, C.I.; Tiekink, E.R.T.; Heard, P.J. Dithiocarbamate Complexes of Platinum Group Metals: Structural Aspects and Applications. Inorganics 2021, 9, 60. https://doi.org/10.3390/inorganics9080060
Tan YS, Yeo CI, Tiekink ERT, Heard PJ. Dithiocarbamate Complexes of Platinum Group Metals: Structural Aspects and Applications. Inorganics. 2021; 9(8):60. https://doi.org/10.3390/inorganics9080060
Chicago/Turabian StyleTan, Yee Seng, Chien Ing Yeo, Edward R. T. Tiekink, and Peter J. Heard. 2021. "Dithiocarbamate Complexes of Platinum Group Metals: Structural Aspects and Applications" Inorganics 9, no. 8: 60. https://doi.org/10.3390/inorganics9080060