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Variable combinations of organophosphines in PtP3X derivatives: Structural aspects

  • Milan Melník EMAIL logo and Peter Mikuš
Published/Copyright: January 19, 2021
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Main Group Metal Chemistry
From the journal Main Group Metal Chemistry Volume 44 Issue 1

Abstract

This review covers over fifty Pt (II) complexes of the compositions PtP3X (X = H, OL, NL, BL, Cl, SL, Br, or I). These complexes crystallized in three crystal classes: monoclinic (23 examples) triclinic (17 examples) and orthorhombic (11 examples). The PtP3Cl is most common with 23 examples. There are variable combinations of organophosphines monodentate – P; bidentate- P,P; P,N; P,B; and tridentate – P,P,P; P,O,P; P,N,P; and P,S,P. The structural parameters (Pt–L, L–Pt–L) are analyzed and discussed with an attention to the distortion of a square-planar geometry about the Pt (II) atoms as well as of trans-influence. The sums of Pt–L (x4) bond distances growing with covalent radius of the X-atoms.

Keywords: structure; organophosphines; PtP3X; trans-influence

1 Introduction

The high affinity of the platinum(II) ion for phosphorous enables it to bind effectivity to organophosphines. There are numerous published structural studies on platinum complexes which were classified and analyzed (Holloway and Melník, 2002, 2003, 2004). Research activity on this field is always very active. Organophosphines as a soft P-donor ligands are very useful for building wide variety of platinum complexes. Recently, we classified and analyzed structural data of monomeric organoplatinum complexes with PtP3C inner coordination sphere (Melník and Mikuš, 2017). Another review covers structural data of monomeric platinum(II) coordination complexes with an inner coordination spheres. PtP4, PtP3X (X = H, F, O, N, Cl, S, Br, or I) and PtP2X2 (X = H, F, O, N, CN, or B) in which P-donor ligands are monodentate organomonophosphines (Melník and Mikuš, 2015).

The aim of this survey is to correlate the structural parameters available, for PtP3X (X = H, OL, NL, BL, Cl, SL, Br, or I) derivatives with variable combinations of organophosphines. The data are comparing and discuss with PtP3X in which P-donor ligands are only monodentate organomonophosphines.

2 PtP3X derivatives

There are over fifty examples, in which the inner coordination spheres about the Pt (II) atoms of the composition PtP3X are formed by variable combinations of organophosphines and X atoms.

2.1 PtP3H type

There are five examples of this type. In orthorhombic dark red [Pt(η2-P7)(PPh3)(H)][K(2,2,2-cryptate)]2 (Charles et al., 1996), the chelating P7 ligand creates four-membered metallocyclic ring with the value of P1–Pt–P2 bite angle of 78.2(4)° (P1PP2). The mean value of the remaining cis-P–Pt–P bond angles is 98.0°, and trans-P1–Pt–P3 bond angle is 174.5°. The Pt–P bond distances are: 2.42(1) Å (Pt–P2, trans to H), 2.40(1) Å (Pt–P1), and 2.23(1) Å (Pt–PPh3).

In another three examples two monoclinic [Pt{η2-Et2P(CH2)2PEt2}{P(BH3)Ph2}(H)] (at 150 K) (Jaska et al., 2003), [Pt{η2-(cy-hexyl)2P(CH2)2P(cy-hexyl)2}{P(BH3)Ph2} (H)] (at 150 K) (Jaska et al., 2005) and orthorhombic [Pt{η2-(η2-C6H12)P(C6H4)P(η2-C6H12)}{P(C15H23)Ph}(H)] (at 238 K) (Kovacik et al., 2000), each chelating-P1,P2 ligand creates five-membered metallocyclic ring with the values of P1–Pt–P2 bite angles of 86.0° and 87.1° (Jaska et al., 2003), 87.1° (Jaska et al., 2005), and 86.9° (Kovacik et al., 2000) (P1C2P2). The monodentate P3R3 with hydride completed a distorted square-planar geometry about Pt(II) atoms. The remaining L–Pt–L bond angles open in the sequence: (mean values): 82.7(±0.5)° (P3–Pt–H) < 91.0(±1.9)° (P1–Pt–H) < 100.0(±3.2)° (P2–Pt–P3) < 171.8((±2.6)° (P2–Pt–H). The Pt–L distance elongate in the sequence (mean values): 1.65(±0.6) Å (Pt–H) < 2.251(±0.02) Å (Pt–P1) < 2.302(±0.01) Å (Pt–P2, trans to H) < 2.328(±0.01) Å (Pt–P3).

In triclinic [Pt{η2-Ph2P(C20H12)PPh2}(PMe3)(H)]BF4 (Figure 1) (Campbell and Gagne, 2007), the chelating P1P2 ligand creates seven membered metallocyclic ring with the value of P1–Pt–P2 bite angle of 97.9° (P1C4P2). The P3Me3 with hydride completed inner coordination sphere about Pt(II) atom. The remaining L–Pt–L bond angles open in the sequence: 66.1° (P3–Pt–H) < 101.8° (P1–Pt–H) < 171.4° (P2–Pt–H). The Pt–L bond distance elongate in the sequence: 1.63 Å (Pt–H) < 2.113 Å (Pt–P1) < 2.306 Å (Pt–P2, trans to H) < 2.322 Å (Pt–P3).

Figure 1 Structure of [Pt{η2-Ph2P(C20H12)PPh2}(PMe3)(H)]+ (Campbell and Gagne, 2007).
Figure 1

Structure of [Pt{η2-Ph2P(C20H12)PPh2}(PMe3)(H)]+ (Campbell and Gagne, 2007).

2.2 PtP3O type

There are three examples of this type. In triclinic [Pt{η3-Ph2P(CH2)2P(Ph)(CH2)2PPh2}(ONO2)](NO3) (Fernandez et al., 2001) and monoclinic [Pt{η3-Ph2P(CH2)2P(Ph)(CH2)2PPh2} {OS(=O)2CF3}](O3SCF3) (Annibale et al., 2000) the tridentate P1,P2,P3-donor ligand creates a pair of five-membered metallocyclic rings with the common P2 atom of the type P1C2P2C2P3, with the mean value of P1–Pt–P2/P2–Pt–P3 angles of 84.3(±1.7)°. The mean value of the remaining L–Pt–L bond angles are: 166.0(±1.4)° (P1–Pt–P3), 95.3(±4.8)° (P1–Pt–O/P3–Pt–O), and 173.7(±2.1)° (P2–Pt–O). The mean value of Pt–L bond distance elongate in the sequence: 2.109(±0.7) Å (Pt–O) < 2.196(±0.011) Å (Pt–P2, trans to O) < 2.318(±0.006) Å (Pt–P1,3, trans to P).

In monoclinic [Pt{η3-Ph2P(C15H12O)PPh2}{PPh2(C5H4N)}] (O3SCF3)2·0.5H2O (at 150 K) (Figure 2) (Lenero et al., 2013) tridentate-P1, O1, P2 donor ligand creates a pair of five-membered metallocycles with common O1 atom of the P1C2O1C2P2 type, with the mean value of P1–Pt–O1/O1–Pt–P2 angles of 81.6(±0.7)°. The values of the remaining L–Pt–L bond angles are: 98.5(±1.7)° (P1–Pt–P3/P2–Pt–P3), 162.2° (P1–Pt–P2), and 174.8° (O1–Pt–P3). The Pt–L bond distance elongate in the sequence: 2.189 Å (Pt–O) < 2.239 Å (Pt–P3, trans to O) < 2.305(±0.07) Å (Pt–P1, Pt–P2).

Figure 2 Structure of [Pt{η3-Ph2P(C15H12O)PPh2}{P(C5H4N)(Ph)2}]2+ (Lenero et al., 2013).
Figure 2

Structure of [Pt{η3-Ph2P(C15H12O)PPh2}{P(C5H4N)(Ph)2}]2+ (Lenero et al., 2013).

2.3 PtP3N type

There are four examples of this type. In triclinic [Pt{η3-(η1-C28H45)P(=CH(C5H3N)CH=)P(η1-C28H45)}(PPh3)]2CH2Cl2 (at 103 K) (Takeuchi et al., 2016) tridentate P1,N1,P2-donor ligand creates a pair of five-membered metallocycles with common N1 atom of the P1C2N1C2P2 type, with the mean value of P1–Pt–N1/N1–Pt–P2 bond angles of 81.0(±0.5)°. The values of the remaining L–Pt–L bond angles are: 98.2(±2.1)° (P1–Pt–P3R3, P2–Pt–P3), 158.7° (P1–Pt–P2), and 173.0°(N1–Pt–P3). The Pt–L bond distance elongate in the sequence: 2.082 Å (Pt–N) < 2.270 Å (Pt–P3, trans to N) < 2.313(±0.012) Å (Pt–P1, Pt–P2).

In monoclinic [Pt{η2-Ph2P(C4H4NO)PPh2-P1,P2} {η2-Ph2P(C4H4NO)PPh2-P3,N}]·CH2Cl2 (at 173 K) (Figure 3) (Zhang et al., 2011) a distorted square-planar arrangement about the Pt(II) atom is build up by two chelating ligands one homo- via P1,P2 – and another one hetero – via P3,N atoms. The former creates four–membered metallocycle with the value of P1–Pt–P2 bite angle of 71.0° (P1CP2) and the latter forms five–membered metallocycle with the value of P3–Pt–N bite angle of 80.9° (P3C2N). The remaining L–Pt–L bond angles open in the order: 102.8° (P2–Pt–N) < 105.2° (P1–Pt–P3) < 173.4° (P1–Pt–N) < 176.0° (P2–Pt–P3). The Pt–L bond distance elongate in sequence: 2.047 Å (Pt–N) < 2.270 Å (Pt–P1, trans to N) < 2.230 Å (Pt–P2) < 2.322 Å (Pt–P3).

Figure 3 Structure of [Pt{η2-Ph2P(C4H4NO)PPh2-P1,P2} {η2-Ph2P(C4H4NO)PPh2-P3,N}] (Zhang et al., 2011).
Figure 3

Structure of [Pt{η2-Ph2P(C4H4NO)PPh2-P1,P2} {η2-Ph2P(C4H4NO)PPh2-P3,N}] (Zhang et al., 2011).

In remaining two examples, triclinic [Pt{η2-Ph2P (C12H8O)PPh2-P1,P2}{η2-Ph2P(C5H4N)-P3,N}](O3SCF3)2·3CH2Cl2 (at 150 K), and monoclinic [Pt{η2-Ph2P(C14H12OSi)PPh2-P1P2} {η2-Ph2P(C5H4N)-P3,N}](O3SCF3)·CH2Cl2 (at 180 K) (Lenero et al., 2013) a distorted square-planar arrangement about each Pt(II) atom is build up by homo-chelating ligand via P1,P2- donor atoms and hetero-chelating ligand via P3,N donor atoms. Each homo-chelating ligand creates eight-membered metallocycle (P1C2O1C2P2) and hetero-chelating creates four-membered metallocycle (P3CN). The mean values of the respective metallocycles are: 94.4(±2.0)° (P1–Pt–P2) and 69.1(±0.1)° (P3–Pt–N). The remaining L–Pt–L bond angles open in the sequence (mean values): 94.4(±2.1)° (P3–Pt–N) < 99.3(±0.1)° (P1–Pt–P2) < 161.1(±3.8)° (P1–Pt–P3) < 168.3(±0.2)° (P2–Pt–N). The Pt–L bond distance elongate in the sequence (mean values): 2.111(±0.1) Å (Pt–N) < 2.272(±0.007) Å (Pt–P2, trans to N) < 2.336(±0.017) Å (Pt–P1, Pt–P3).

2.4 PtP3B type

Two triclinic complexes are of this type. Both complexes: [Pt{η2-But2PB(C6F5)2}(PPh3)2] (at 193 K) and [Pt{η2-(cyhexyl)2PB(C6F5)2}(PPh3)2] (at 193 K) (Figure 4) (Amgoune et al., 2012) are isostructural. The inner coordination sphere about each platinum atom is build up by heterobidentate donor ligand via P,B donor atoms and two monodentate PPh3 ligands completed distorted tetrahedral geometry (PtP3B). Each heterobidentate ligand creates three membered metallocyclic ring with mean P1–Pt–B bite angles of 49.6(±0.4)° (P1B). The remaining L–Pt–L bond angles open in the sequence (mean values): 101.4(±0.5)° (P2–Pt–P3) < 101.6(±1.5)° (P3–Pt–B) < 109.0(±0.1)° (P1–Pt–P2) < 148.0(±1.5) (P1–Pt–P3) < 156.5(±2.5)° (P2–Pt–B). The Pt–L bond distance elongate in the sequence (mean values): 2.262(±0.028) Å (Pt–B) < 2.310(±0.012) Å (Pt–P1) < 2.319(±0.023) Å (Pt–P3) < 2.356(±0.018) Å (Pt–P2, trans to B).

Figure 4 Structure of [Pt{η2-(cy-hexyl)2PB(C6F5)2}(PPh3)2] (Amgoune et al., 2012).
Figure 4

Structure of [Pt{η2-(cy-hexyl)2PB(C6F5)2}(PPh3)2] (Amgoune et al., 2012).

2.5 PtP3Cl type

In two colorless one triclinic [Pt{η2-Ph2PN(CH)PPh2} {P(Me)2Ph}Cl]Cl and orthorhombic [Pt{η2-Ph2PN(H)PPh2} (PBut3)Cl]Cl (Bhattacharyja et al., 1993) a distorted square-planar environment about each Pt(II) atom is build up by chelating P1,P2- donor ligand, with P3R3 donor ligand and chlorine. The chelating ligand creates four-membered metallocycle with the mean value of P1–Pt–P2 bite angle of 69.8(±0.2)° (P1NP2). The mean values of remaining cis-L–Pt–L bond angles are: 102.8(±1.1)° (P–Pt–P) and 93.6(±5.3)° (P3–Pt–Cl). The Pt–L bond distance elongate in the sequence (mean values): 2.228(±0.001) Å (Pt–P2, trans to Cl) < 2.305(±0.008) Å (Pt–P1) < 2.331(±0.001) Å (Pt–P3) < 2.351(±0.005) Å (Pt–Cl).

In two monoclinic [Pt{η2-Ph2P(CH2)PPh2}{P(cyclenH2} Cl](BF4)2·MeCN (Khasnis et al., 1992), [Pt{η2-tpbp) (PEt3)Cl] (Caliman, 1998) and triclinic [Pt{η2-Ph2P(CH2) PPh2}{P(C18H9)Ph2}Cl]CF3SO3·CH2Cl2 (Hu et al., 2009) each chelating –P1,P2 ligand creates four-membered metallocyclic ring with the mean value of P1–Pt–P2 bite angle of 71.5(±0.4)° (P1CP2). The remaining L–Pt–L bond angles are: 97.8(±2.4)° (P–Pt–P),168.2(±0.1)° (P–Pt–P), 95.1(±2.0)° (P–Pt–Cl), and 166.3(±1.8)° (P–Pt–Cl). The Pt–L bond distance elongate in the sequence (mean values): 2.255(±0.008) Å (Pt–P2, trans to Cl) < 2.315(±0.016) Å (Pt–P1) < 2.319(±0.003) Å (Pt–P3) < 2.360(±0.02) Å (Pt–Cl).

In monoclinic [Pt{η2-ButP1(PBut)2PP2But}{P3(Me)2Ph}Cl] (at 223 K) (Figure 5) (Gomez-Ruiz et al., 2007), the chelating ligand creates four-membered metallocyclic ring with the value of P1–Pt–P2 bite angle of 79.9°(P1PP2). The values of the remaining cis-L–Pt–L bond angles open in the sequence: 85.9° (P3–Pt–Cl) < 96.8° (P1–Pt–Cl) < 97.7° (P1–Pt–P3), and trans-P2–Pt–Cl bond angle is 175.3°. The Pt–L bond distance elongate in the sequence: 2.301 Å (Pt–P2, trans to Cl) < 2.309 Å (Pt–P1) < 2.327 Å (Pt–P3) < 2.415 Å (Pt–Cl).

Figure 5 Structure of [Pt{η2-ButP1(PBut)2PP2But}{P3(Me)2Ph}Cl] (Gomez-Ruiz et al., 2007).
Figure 5

Structure of [Pt{η2-ButP1(PBut)2PP2But}{P3(Me)2Ph}Cl] (Gomez-Ruiz et al., 2007).

There are six examples: triclinic [Pt{η2-(Me)(Ph) P(C6H4){P(Ph)(Me)}{(P(H)(Me)(Ph)}Cl]PF6·CH2Cl2 (Bader et al., 1992, 1995), monoclinic [Pt{η2-(η2-(C6H12)P(C6H4) P(η2-C6H12)}{P(=O)(Me)(C15H23)}Cl]·0.5toluene (at 208 K), orthorhombic [Pt{η2-(η2-C6H12)P(C6H4)P(η2-C6H12)}{P(Me) (C15H23)}Cl]·C6D6 (at 100 K), and orthorhombic [Pt{η2-(η2-C6H12)P(C6H4)P(η2-C6H12)}{P(H)(C15H23)}Cl](BPh4)·CH2Cl2 (at 208 K) (Scriban et al., 2006), orthorhombic [Pt{η2-Ph2P(C4H8)PPh2}(P(Me)Ph2}Cl]PF6 (Gugger et al., 1993), and triclinic [Pt{η2-Ph2P(C2B9H10)PPh2}(PPh3)Cl]·2CH2Cl2·H2O (Zhang et al., 2006), in which each chelating –P1, P2 donor ligand creates five-membered metallocyclic ring with the mean value of P1–Pt–P2 bite angle of 86.2(±0.9)° (P1C2P2). The values of the remaining L–Pt–L bond angles open in the sequence (mean values): 87.5(±2.7)° (P1–Pt–Cl) < 92.4(±3.0)° (P3–Pt–Cl) < 94.3(±4.7)° (P2–Pt–P3) < 172.9(±6.8)° (P1–Pt–P3) < 173.2(±1.5)° (P2–Pt–Cl). The Pt–L bond distance elongate in the sequence (mean values): 2.230(±0.023) Å (Pt–P2, trans to Cl) < 2.286(±0.017) Å (Pt–P1) < 2.345(±0.032) Å (Pt–P3) < 2.360(±0.015) Å (Pt–Cl).

In monoclinic [Pt{η2-Me2P(OB(F2)O)PMe2}(PEt3)Cl] (Roundhill and Roundhill, 1982) a distorted square-planar geometry about Pt (II) atom is build up by chelating – P1,P2 donor ligand, monodentate PEt3 and Cl atom. The chelating ligand creates six–membered metallocyclic ring with the value of P1–Pt–P2 bite angle of 92.4° (P1OBOP2). The values of the remaining L–Pt–L bond angles are: 94.4° (P2–Pt–P3), 86.6(±0.8)° (P1–Pt–Cl; P3–Pt–Cl), 172.5° (P1–Pt–P3), and 178.6° (P2–Pt–Cl). The Pt–L bond distance elongate in the sequence: 2.194(5) Å (Pt–P2, trans to Cl) < 2.263(6) Å (Pt–P1) < 2.338 (6) Å (Pt–Cl) < 2.340(6) Å (Pt–P3).

In another monoclinic [Pt{η2-Ph2P(C20H12)PPh2}(PMe3) Cl]BF4 (Campbell and Gagne, 2007), the chelating-P1,P2-donor ligand creates seven-membered metallocycle ring with P1–Pt–P2 bite angle of 92.3° (P1C4P2). The remaining L–Pt–L bond angles open in the sequence: 87.5° (P3–Pt–Cl) < 88.9° (P1–Pt–Cl) < 97.8° (P2–Pt–P3) < 161.0° (P1–Pt–P3) < 164.4° (P2–Pt–Cl). The Pt–L bond distance elongate in the sequence: 2.245 Å (Pt–P2, trans to Cl) < 2.323 Å (Pt–P3) < 2.359 Å (Pt–Cl).

There are seven examples: monoclinic [Pt{η3-Ph2P(CH2)2P(Ph)(CH2)2PPh2}Cl] [Sn(Ph)2Cl4] and triclinic [Pt{η3-Ph2P(CH2)2P(Ph)(CH2)2PPh2}Cl][SnPh2Cl3] (Garcia-Seijo et al., 2001), monoclinic [Pt{η3-Ph2P(CH2)2 P(Ph)(CH2)2PPh2}Cl](CuCl2)- (Fernandez et al., 2005), monoclinic [Pt{η3-(cy-hexyl)2P(CH2)2P{(CH2CH2P(=O) (cy-hexyl)2(CH2)2P(cy-hexyl)2}Cl]·0.5CH2Cl2·4H2O (Reickborn et al., 2009), monoclinic [Pt{η3-Pri2P(C6H4) P(C6H4)P Pri2}Cl] (at 100 K) (Mazzeo et al., 2011), and monoclinic [Pt{η3-Ph2P(C26H23OP)P(Ph)(CH26H23OP)PPh2} Cl]PF6·4MeOH (at 160 K) (Clegg and Elsegood, 2017) in which each tridentate ligand creates a pair of five–membered metallocycles (P1C2P2C2P3); with common P2 atom. The mean value of the (P1–Pt–P2/P2–Pt–P3) bite angles is 85.4(±1.5)°. The remaining L–Pt–L bond angles open in the sequence (mean values): 93.9(±1.3)° (P1–Pt–Cl) < 95.1(±0.8)° (P3–Pt–Cl) < 167.2(±2.3)° (P1–Pt–P3) < 176.0(±1.7)° (P2–Pt–Cl). The Pt–L bond distance elongate in the order (mean values): 2.210(±0.002) Å (Pt–P2, trans to Cl) < 2.310(±0.009) Å (Pt–P1) ~2.310(±0.011) Å (Pt–P3) < 2.357(±0.008) Å (Pt–Cl).

In orthorhombic [Pt{η3-Ph2P(CH2)3P(Ph)(CH2)3PPh2} Cl]ClO4 (at 145 K) (Klint et al., 2004) and triclinic [Pt{η3-Pri2P(C11H8)P(Pri)(C11H8)PPri2}Cl]Cl.CH2Cl2 (Ray et al., 2013), tridentate P1,P2,P3 donor ligand creates a pair of six–membered metallocyclic rings with common P2 atom and Cl completed a distorted square-planar geometry about Pt(II) atom. The mean values of P1–Pt–P2/P2–Pt–P3 bite angles is 92.5(±0.9)° (P1C3P2C3P3). The remaining L–Pt–L bond angles open in the sequence: 86.8° (P3–Pt–Cl) < 88.0° (P1–Pt–Cl) < 171.6° (P1–Pt–P3) < 179.4° (P2–Pt–Cl). The Pt–L bond distance elongate in the sequence: 2.239 Å (Pt–P2, trans to Cl) < 2.302 Å (Pt–P1) < 2.313 Å (Pt–P3) < 2.365 Å (Pt–Cl).

In monoclinic [Pt{η3-Ph2P(C6H4)(C2H4N2P(Cl) (C6H4)2PPh2}Cl]PF6 (at 120 K) (Day et al., 2011), and monoclinic [Pt{η3-Ph2 P(C6 H4){N(CH2)2 N}P(C6 H4)2 P P h2 }Cl]PF6 (at 120 K) (Pan et al., 2012a), tridentate P1,P2,P3- donor ligand creates a pair of six-membered metallocyclic rings with common P2 atom (P1C2NP2NC2P3) with Cl build up a distorted square-planar geometry about Pt(II) atom. The mean value of P1C2NP2/P2NC2P3 bite angles is 89.2(±1.6)°. The remaining L–Pt–L bond angles open in the sequence: 88.6° (P3–Pt–Cl) < 92.7° (P1–Pt–Cl) < 174.7° (P1–Pt–P3) < 179.4° (P2–Pt–Cl). The bond distance elongate in the sequence: 2.155 Å (Pt–P2, trans to Cl) < 2.298 Å (Pt–P1) < 2.302 Å (Pt–P3) < 2.334 Å (Pt–Cl).

2.6 PtP3S type

There are seven examples of this type. In yellow triclinic [Pt{η2-Ph2P(CH2)PPh2}{η2-Ph2PN(Et)C=(NEt)S}] (Okeya et al., 1992) two bidentate donor ligands, one homo-(P1,P2) and another one hetero-(P3, S) build up a distorted square-planar geometry about platinum atom. The homobidentate creates a four-membered metallocyclic ring with the value of P1–Pt–P2 bite angle of 71.4° (P1CP2) and hetero-creates five-membered with the value of P3–Pt–S bite angle of 85.7° (P3NCS). The remaining L–Pt–L bond angles open in the sequence: 96.8° (P1–Pt–S) < 108.6° (P2–Pt–P3) < 164.8° (P2–Pt–S) < 177.20° (P1–Pt–P3). The Pt–L bond distance elongate in the sequence: 2.269 Å (Pt–P2, trans to S) < 2.291 Å (Pt–S) < 2.303 Å (Pt–P1) < 2.309 Å (Pt–P3).

In yellow three monoclinic [Pt{η3-Ph2P(CH2)2P(Ph) (CH2)2PPh2}{η1-Et2NCS2}] (Colton et al., 1993), monoclinic [Pt{η3-Ph2P(CH2)2P(Ph)(CH2)2PPh2}(SPh)]CF3SO3, [Pt{η3-Ph2P(CH2)2P(Ph)(CH2)2PPh2}(SC6HF4)]CF3SO3, and triclinic [Pt{η3-Ph2P(CH2)2P(Ph)(CH2)2PPh2}(SC6F4(CF3))]CF3SO3 (Cervantes et al., 2015), each tridentate -P1,P2,P3- donor ligand creates a pair of five-membered metallocycles with common P2 atom (P1C2P2C2P3) with the mean value of P1–Pt–P2/P2Pt–P3 bite angles of 85.0(±0.6)°. The mean value of cis-P–Pt–S bond angles is 92.7(±3.1)°. The Pt–L bond distance elongate in sequence: 2.233 Å (Pt–P2, trans to S) < 2.287 Å (Pt–P1) < 2.396 Å (Pt–S).

In triclinic [Pt{η3-Ph2P(C6H4)S(=O)(C6H4)PPh2} (PPh3)]·0.5CH2Cl2 (at 100 K) (Figure 6) (Suess and Peters, 2012) and orthorhombic [Pt{η3-Ph2P(CH2)2S(CH2)2PPh2} PPh3)](ClO4)2.Me2CO (at 120 K) (Andreasen et al., 2002), tridentate –P1–S1–P2–donor ligand creates a pair of five–membered metallocycles with common S1 atom (P1C2S1C2P2). The mean value of P1C2S1/S1C2P2 bite angles is 89.0(±0.3)°. The Pt–L bond distance elongate in the sequence: 2.271 Å (Pt–P1) < 2.276 Å (Pt–P2) < 2.281 Å (Pt–P3, trans to S) < 2.313 Å (Pt–S).

Figure 6 Structure of [Pt{η3-Ph2P(C6H4)S(=O)(C6H4)PPh2}(PPh3)] (Suess and Peters, 2012).
Figure 6

Structure of [Pt{η3-Ph2P(C6H4)S(=O)(C6H4)PPh2}(PPh3)] (Suess and Peters, 2012).

2.7 PtP3Br type

Yellow triclinic [Pt{η2-But2PP=P But2}(PPh3)Br] (at 243 K) (Figure 7) (Kovacs et al., 1997) is only example of this type. The chelating –P1,P2–donor ligand with P3Ph3 and Br anion build up a distorted square-planar geometry about Pt atom. The chelating ligand forms three membered metallocycle with the value of P1–Pt–P2 bite angle of 55.1° (P1P2). The Pt–L bond distance elongate in the sequence: 2.231 Å (Pt–P1, trans to Br) < 2.297 Å (Pt–P2) < 2.405 Å (Pt–P3) < 2.410 Å (Pt–Br). The mean value of cis-P–Pt–Br bond angles is 96.1(±5.3)°.

Figure 7 Structure of [Pt{η2-But2PP=P But2}(PPh3)Br] (Kovacs et al., 1997).
Figure 7

Structure of [Pt{η2-But2PP=P But2}(PPh3)Br] (Kovacs et al., 1997).

2.8 PtP3I type

There are three examples of this type. In yellow orthorhombic [Pt{η2-(η2-C6H12)P(C6H4)P(η2-C6H12)}{P(Me) (C15H23)}I] (at 203 K) (Scriban et al., 2006) the chelating –P1,P2 donor ligand creates five-membered metallocyclic ring with value of P1–Pt–P2 bite angle of 86.1° (P1C2P2). The Pt–L bond distance elongate in the sequence: 2.231 Å (Pt–P2, trans to I) < 2.291 Å (Pt–P1) < 2.393 Å (Pt–P3) < 2.640 Å (Pt–I). The value of cis-P2–Pt–P3bond angle is 94.9°, trans-P1–Pt–P3 bond angle is 169.0° and trans–P2–Pt–I is 172.0°.

In orthorhombic [Pt{η3-Ph2P(CH2)2P(Ph)(CH2)2PPh2} I]·0.2CHCl3·0.5H2O (at 220 K) (Parsons et al., 2004) tridentate –P1,P2,P3 donor ligand creates a pair of five-membered metallocyclic rings with the common P2 atom (P1C2P2C2P3) with the value of P1–Pt–P2/P2–Pt–P3 bite angle of 84.9°. The values of Pt–L bond distances are: 2.249 Å (P2, trans to I) < 2.309 Å (P1, P3) and 2.64 Å (I).

In monoclinic [Pt{η3-Ph2P(C6H4){N(CH2)2N}P(Me) (C6H4)PPh2}I]PF6·CH2Cl2 (at 120 K) (Figure 8) (Pan et al., 2012b). As can be seen the tridentate –P1,P2,P3–donor ligand creates a pair of six-membered metallocyclic rings with the common P2 atom (P1C2NP2N C2P3). The mean value of P1–Pt–P2/P2–Pt–P3 bite angles is 87.2(±2.1)°. The values of remaining L–Pt–L bond angles are: 92.8° (P1,3–Pt–I), 173.5° (P1–Pt–P3), and 175.0° (P2–Pt–I). The Pt–L bond distance elongate in the sequence: 2.227 Å (Pt–P2, trans to I) < 2.312 Å (Pt–P3) < 2.322 Å (Pt–P1) < 2.638 Å (Pt–I).

Figure 8 Structure of [Pt{η3-Ph2P(C6H4){N(CH2)2N}P(Me)(C6H4)PPh2}I]+ (Pan et al., 2012b).
Figure 8

Structure of [Pt{η3-Ph2P(C6H4){N(CH2)2N}P(Me)(C6H4)PPh2}I]+ (Pan et al., 2012b).

3 Conclusions

This review includes over fifty monomeric Pt(II) coordination complexes with composition of PtP3X (X = H, OL, NL, BL, Cl, SL, Br, or I). These complexes crystallized in three crystal classes: monoclinic (23 examples), triclinic (17 examples), and orthorhombic (11 examples). On the basis of variable combination of donor ligands which build up PtP3X, can be divided into the five sub-groups.

To each sub-group the bond distance (mean values) with sums of Pt–L(x4) bond distances are:

I. Pt(η2-P1,P2L)(P3L)X:

PtP3H: 2.253 Å (Pt–P1); 2.326 Å (Pt–P2, trans to H); 2.310 Å (Pt–P3); 1.65 Å (Pt–H); Σ 8.54 Å (Campbell and Gagne, 2007; Charles et al., 1996; Jaska et al., 2003, 2005; Kovacik et al., 2000).

PtP3Cl: 2.290 Å (Pt–P1); 2.226 Å (Pt–P2, trans to Cl); 2.334 Å (Pt–P3); 2.357 Å (Pt–Cl); Σ 9.21 Å (Bader et al., 1992, 1995; Bhattacharyja et al., 1993; Caliman, 1998; Campbell and Gagne, 2007; Gomez-Ruiz et al., 2007; Gugger et al., 1993; Hu et al., 2009; Khasnis et al., 1992; Roundhill and Roundhill 1982; Scriban et al., 2006; Zhang et al., 2006).

PtP3Br: 2.291 Å (Pt–P1); 2.231 Å (Pt–P2, trans to Br); 2.405 Å (Pt–P3); 2.510 Å (Pt–Br); Σ 9.44 Å (Kovacs et al., 1997).

PtP3I: 2.290 Å (Pt–P1); 2.300 Å (Pt–P2, trans to I); 2.393 Å (Pt–P3); 2.640 Å (Pt–I); Σ 9.56 Å (Scriban et al., 2006).

II. Pt(η2-P1,P2L)(η2-P3,X):

PtP3N: 2.324 Å (Pt–P1); 2.271 Å (Pt–P2, trans to N); 2.340 Å (Pt–P3); 2.079 Å (Pt–N); Σ 9.01 Å. (Lenero et al., 2013; Zhang et al., 2011).

PtP3S: 2.309 Å (Pt–P1); 2.303 Å (Pt–P2, trans to S); 2.269 Å (Pt–P3); 2.291 Å (Pt–S); Σ 9.17 Å (Okeya et al., 1992).

III. Pt(η3-P1,P2,P3L)X:

PtP3O: 2.322 Å (Pt–P1); 2.196 Å (Pt–P2, trans to O); 2.315 Å (Pt–P3); 2.109 Å (Pt–O); Σ 8.94 Å (Annibale et al., 2000; Fernandez et al., 2001).

PtP3Cl: 2.300 Å (Pt–P1); 2.197 Å (Pt–P2, trans to Cl); 2.307 Å (Pt–P3); 2.349 Å (Pt–Cl); Σ 9.15 Å (Clegg and Elsegood, 2017; Day et al., 2011; Fernandez et al., 2005; Klint et al., 2004; Mazzeo et al., 2011; Pan et al., 2012a; Ray et al., 2013; Reickborn et al., 2009).

PtP3S: 2.292 Å (Pt–P1); 2.233 Å (Pt–P2, trans to S); 2.293 Å (Pt–P3); 2.393 Å (Pt–S); Σ 9.21 Å (Cervantes et al., 2015; Colton et al., 1993).

PtP3I: 2.312 Å (Pt–P1); 2.227 Å (Pt–P2, trans to I); 2.322 Å (Pt–P3); 2.638 Å (Pt–I); Σ 9.50 Å (Pan et al., 2012b; Parsons et al., 2004).

IV. Pt(η3-P1,X1,P2)(P3L):

PtP3O1: 2.297 Å (Pt–P1); 2.312 Å (Pt–P2); 2.239 Å (Pt–P3, trans to O); 2.189 Å (Pt–O); Σ 9.04 Å (Lenero et al., 2013).

PtP3N1: 2.309 Å (Pt–P1); 2.325 Å (Pt–P2); 2.270 Å (Pt–P3, trans to N); 2.082 Å (Pt–N); Σ 8.98 Å (Takeuchi et al., 2016).

PtP3S1: 2.271 Å (Pt–P1); 2.276 Å (Pt–P2); 2.281 Å (Pt–P3, trans to S); 2.313 Å (Pt–S); Σ 9.14 Å (Andreasen et al., 2002; Suess and Peters, 2012).

V. Pt(η2-P1, BL)(PPh3)2:

PP3B: 2.310 Å (Pt–P1); 2.354 Å (Pt–P2, trans to B); 2.340 Å (Pt–P3); 2.262 Å (Pt–B); Σ 9.27 Å (Amgoune et al., 2012).

The Pt–P (rans to X) bond distance elongate in the sequence (total mean values): 2.212 Å (X=Cl) < 2.218 Å (OL) < 2.231 Å (Br) < 2.264 Å (I) < 2.270 Å (NL) < 2.272 Å (SL) < 2.326 Å (H); which corresponds quite well with trans influence of the respective X- donor atoms. The total mean values of Pt–P (bis and tridentate) and Pt–PR3 (monodentate) bond distances (mutually trans) are: 2.288 and 2.326 Å. The Pt–X (trans to P) bond distance elongate in the sequence (total mean values): 1.65 Å (X=H) < 2.086 Å (NL) < 2.150 Å (OL) < 2.262 Å (BL) < 2.332 Å (SL) < 2.353 Å (Cl) < 2.510 Å (Br) < 2.639 Å (I). The sum of Pt–L(x4) bond distances growing in the sequence: 8.54 Å (PtP3H) < 8.97 Å (PtP3O) < 9.00 Å (PtP3N) < 9.17 Å (PtP3S) < 9.19 Å (PP3Cl) < 9.27 Å (PtP3B) < 9.44 Å (PtP3Br) < 9.52 Å (PtP3I); which corresponds quite well with covalent radii of X atoms, except S and B atoms.

The chelating ligands create wide varieties of the metallocyclic rings: three- PB, PP; four- PCN, PCP, PPP; five- PC2N, PC2O, PC2P, PC2S; six- PC3P, POBOP; seven-PC4P; and eight-PC2OC2P, membered. There are at least two contributing factors to the size of chelate bond angles both ligand based. One is the steric constraints imposed on the ligand and the other is the need to accommodate bidenticity there appropriate. The L–Pt–L chelate bond angles open in the sequence (mean values): 49.6° (PB) < 55.1° (PP) < 69.1° (PCN) < 71.2° (PCP) < 78.2° (PPP) < 81.0° (PC2N) < 81.7° (PC2O) < 86.3° (PC2P) < 89.0° (PC2S) < 92.4° (POBOP) < 92.5° (PC3P) < 94.4° (PC2OC2P) < 95.1° (PC4P).

In transition metal complexes, the oxidation state plays a leading role in the geometry formed and platinum is no exception. In four coordinate Pt(II) prefer a square planar geometry. The utility of a simple metric to assess molecule shape and degree of distortion as well as exemplified best the τ4 parameter for a square-planar geometry by equation introduced by (Yang et al., 2007):

(1) τ4=360-(α+β)141for tetrahedral, andτ4=360-(α+β)360for square planar

The values of τ4 range from 0.00 for the perfect square-planar geometry to 1.00 for a perfect tetrahedral geometry, since 360-2(109.5) = 141.

The total mean values of τ4 for the respective complexes with the PtP3X chromophores, growing in the sequence: 0.040 (PtP3H) < 0.042 (PtP3I) < 0.045 (PtP3Br) < 0.049 (PtP3Cl) < 0.050 (PtP3S) < 0.056 (PtP3O) < 0.065 (PtP3N) < 0.15 (PtP3B). The distortion of the square-planar geometry increases in the given sequence there is a cooperative effect between a degree of distortion and trans influence o X atom/ligand, when trans-influence of the respective X weakness degree of distortion increases.

During the collection and organization of the data has become evident that some original papers are lacking important information such as atom coordinates and analysis of intermolecular distances. In view of these limitations we believe that such review as this can continue to serve a useful function by centralizing available material and delineating areas worthy of further investigation.

Acknowledgements

This work was supported by the projects VEGA 1/0463/18, KEGA 027UK-4/2020, and APVV-15-0585.

Abbreviations:

But2PB(C6F5)2

bis(pentafluorophenyl)boryl(di-t-butyl)phosphine

ButP(PBut)2PPBut

(2,3,4-tri-t-butyl-1-(t-butylphosphido) cyklotetraphosphan-2-yl)

(cy-hexyl)2P(CH2)2P (cy-hexyl)2

1,2-bis(dicyclohexylphosphine) ethane

(cy-hexyl)2P(CH2)2P {(CH2CH2P(=O) (cy-hexyl)2(CH2)2P (cy-hexyl)2

((2-(dicyclohexyl-phosphanoyl)ethyl)bis(2-(dicyclohexylphosphanyl)ethyl) phosphene

(cy-hexyl)2PB(C6F5)2

(bis(pentafluorophenyl)boryl) (dicyclohexyl)phosphine

(η1-C28H45) P(=CH(C5H3N)=CH) P(η1-C28H45)

(2,6-bis{[(1,1,3,3,5,5,7,7-octaethyl-1,2,3,4,5,6,7-hexahydro-3-indacen4-yl)phosphanylidene] methyl}pyridine)

(η2-C6H12)P(1,2-C6H4)P (η2-C6H12)

1,2-bis(2,5-dimethylphophatano) benzene

(η2-C6H12)P(C6H4)P (η2-C6H12)

1,2-bis(2,5-dimethylphosphanyl) benzene

Et2P(CH2)2PEt2

1,2-bis(diethylphosphiono) ethane

(Me)(Ph)P(C6H4){P(Ph) (Me)

1,2-bis(methylphenylphosphino) benzene

Me2P(OB(F2)OPMe2

bis(dimethylphosphino) difluoroborate

P(=O)(Me)(C15H23)

methyl(2,4,6-tri-isopropylphenyl)oxophosphanyl

P(BH3)Ph2

boryl(diphenyl)phosphine

P(C15H23)Ph

phenyl(2,4,6-tri-isopropylphenyl)phosphide

P(C18H9)Ph2

1-(diphenylphosphino)pyrene

P(Me)(C15H23)

methyl(2,4,6-tri-isoprophylphenyl)phosphide

P(Me)2Ph

dimethylphenylphosphine

PBut3

tri-t-butylphosphine

Ph2P(C12H8O)PPh2

oxybis(2,1-phenylene) bis(diphenylphosphine)

Ph2P(C14H12OSi)PPh2

(10,10-dimethyl-1,4-phenoxasiline-4,6-diyl)bis diphenylphosphine)

Ph2P(C15H12O)PPh2

bis(diphenylphosphine) (9,9dimethyl-9H-xanthene-4, 5-diyl)

Ph2P(C20H12)PPh2

bis(diphenylphosphine) binaphthalene-2,2-etiyl

Ph2P(C26H23OP)P(Ph) (C26H23OP)PPh2

({(phenylphospanediyl) bis[1-(diphenyl-phosphanyl) ethane-2,1-diyl]}-bis[diphenyl-phosphane oxide])

Ph2P(C2B9H10)PPh2

7,8-bis(diphenylphosphino)-7,8-dicarbamido-undecaborate

Ph2P(C4H4NO)PPh2

bis(2-bis(diphenylphosphino) methylidene)-1,3-oxazolidinido

Ph2P(C5H4N)

2-(diphenylphosphino)pyridine

Ph2P(C6H4){N(CH2)2N} P(C6H4)2PPh2

(1,3-bis(2-(diphenylphosphino) phenyl)-1,3,2-diazaphospholidine)

Ph2P(C6H4){N(CH2)2N} P(Me)(C6H4)PPh2

(1,3-bis(2-(diphenylphosphino) phenyl)-2-methyl-1,3,2-diazaphospholidine)

Ph2P(C6H4)S(=O)(C6H4) PPh2

(sulfinyldi-2,1-phenylene)bis (diphenylphosphine)

Ph2P(CH2)2P(Ph) (CH2)2PPh2

bis(2-diphenylphosphinoethyl) phenylphosphine

Ph2P(CH2)3P(Ph) (CH2)3PPh2

bis(3-diphenylphos phinopropyl)phenylphosphine

Ph2PN(H)PPh2

bis(diphenylphosphino)amine

PMe3

trimethylphosphine

PPh3

triphenylphosphine

Pri2P(C11H8)P(Pri)(C11H8) PPri2

((isopropylphosphinediyl) bis(1,2-di-hydro-6,5-diyl)bis(-isopropylphosphine))

Pri2P(C6H4)P(C6H4)PPri2

((phosphinediyl)di-2,1-phenylene)-bis(di-isopropylphosphinato)

SC6F4(CF3)

2,3,5,6-tetrafluoro-4-(trifluoro methyl)benzenethiolate

SC6HF4

2,3,5,6-tetrafluorobenzenethiolate

SPh

benzenethiolate

tpbp

1,3,5-triphosphabicyklo[2.1.0]-pentin-2-ene

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Received: 2020-08-28
Accepted: 2020-10-20
Published Online: 2021-01-19

© 2021 Milan Melník et al., published by De Gruyter

This work is licensed under the Creative Commons Attribution 4.0 International License.

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https://doi.org/10.1515/mgmc-2021-0003
Keywords for this article
structure; organophosphines; PtP3X; trans-influence
Creative Commons
BY 4.0

Articles in the same Issue

  1. Research Articles
  2. A novel approach for the production of zinc borate (4ZnO·B2O3·H2O) using a single-step hydrothermal method
  3. Fabrication, characterization, and photocatalytic performance of ternary cadmium chalcogenides CdIn2S4 and Cd7.23Zn2.77S10-ZnS thin films
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