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Organophosphines in PtPCOX (X = N, Cl, S), PtPCNX (X = Cl, S, Br, I, As) and PtPCClX (X = S, I, As) derivatives: structural aspects

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Abstract

In this review are classified and analyzed structural parameters of almost 90 monomeric organoplatinum complexes with inner coordination spheres consisting of PtPCOX (X = N, Cl, S), PtPCNX (X = Cl, S, Br, I, As) and PtPCClX (X = S, I, As). These complexes crystallized in three crystal systems: orthorhombic (× 11), triclinic (× 32) and monoclinic (× 45). Distorted square planar arrangements about the Pt(II) atoms are provided by mono-, heterobi- and heterotridentate donor ligands. The chelating ligands create a wide variety of four-, five- and six-membered metallocyclic rings and the effects of both steric and electronic factors influence the L–Pt–L bite angles. There are wide variations in the trans-positions of the donor ligands. Two examples are classified as distortion isomers.

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Abbreviations

bipe:

1,1-Bis(iminophosphoranyl)ethanide

\( {\text{Bu}}_{2}^{{t}} {\text{PCH}}_{2} {\text{C}}_{ 5} {\text{H}}_{4} {\text{N}} \) :

2-(Di-tert-butylphosphinomethyl)pyridine

C5H7OS:

Monothioacetylacetonate

C6H10NO:

1,4-Dimethyl-3-oxo-3-azapenta-1,3-dien-1-yl

C7H12N:

1-(Dimethylamino)-3-methyl-but-2-enyl

C7H4O2S:

Thiosalicylate

C8H10N:

2-(1-Aminoethyl)phenyl

C9H10NO:

2-(((2-Hydroxyethyl)imino)methyl)phenyl

C9H6NS:

2-(2-(2-Pyridyl)thien-3-yl

C9H7N3SCl2 :

2-(1-((Amino(sulfido)methylene)hydrazono)ethyl)-4,5-dichloro-phenyl

C9H9N2O7 :

3,4,5-Trimethoxy-2,6-dinitrophenyl

C9H9N3S:

(2-((Amino(sulfido)methylene)hydrazono)methyl)-5-methylphenyl

C10H11N3S:

4-Methylacetophenone thiosemicarbazone

C10H14N:

2-(1-(Dimethylamino)methyl)phenyl

C10H7N2 :

2,2′-Bipyrid-3-yl

C10H9OS:

3-Mercapto-1-phenylbut-2-en-1-onate

C11H16NO:

2-((Dimethylamino)methyl)-6-(methoxymethyl)phenyl

C11H7FN:

5-Fluoro-2-(pyridin-2-yl)phenyl

C11H8N:

2-Phenylpyridinate

C12H20F6OP:

1,1-Bis(trifluoromethyl)-2-(di-t-butylphosphino)ethanolate

C12H20NSi:

2-(Dimethylaminomethyl)-5-(trimethylsilyl)phenyl

C13H8N2Br:

5-Bromo-2-(imidazo[1,2-a]pyridin-2-yl)phenyl

C14H14N2S:

1-Methyl-3-((phenylsulfanyl)methyl)benzimidazol-2-ylidene

C14H16N:

1-(1-Dimethylamino)ethyl)-2-naphthyl

C14H19PS:

5-Phenyl-1-thia-5-phosphacyclooctane

C14H24NP:

2-(Di-t-butylphosphinomethyl)pyridine

C14H8F6N:

2-(3,5-Bis(trifluoromethyl)phenyl-4-methylpyridine

C14H8N:

Benzo(h)quinolinate

C15H13ClN:

(2-(((4-Chlorobenzyl)imino)methyl)phenyl)methyl

C15H13NCl:

(2-(((4-Chlorobenzyl)imino)methyl)phenyl)methyl

C15H14N:

(2-((Benzylimino)methyl)phenyl)methyl

C15H14N* :

2-((Benzylimino)methyl)-3-methylphenyl

C15H15FN:

2-(6-(4-Fluorophenyl)pyridin-2-yl)-2-methylpropyl

C15H20NO4 :

5-(Ethylmalonyloxymethyl)-2-dimethylaminomethylphenyl

C16H13F6OP:

1,1-Bis(trifluoromethyl)-2-(diphenylphosphino)ethanolate

C16H16NOP:

2-((Diphenylphosphanyl)methyl)-4,5-dihydro-1,3-oxazole

C17H12N2O:

1-((5-Methyl-2-oxidiphenyl)diazenyl)-2-naphthyl

C17H18N2Cl:

3-Chloro-2-(2-dimethylaminoethyliminomethyl)biphenyl

C18H20N:

3,5-Dimethyl-2-((((2-methylbenzyl)imino)methyl)phenyl)methyl

C19H33NP:

(2-(2-Dimethylamino)ethyl)-6-(di-terc-butylphosphinomethyl)phenyl

C20H10ClF5N5 :

2-(((4-Chlorobenzyl)imino)methyl)-2′,3′,4′,5′,6′-pentafluoro-biphenyl-3-yl

C21H16F2N:

2-(((2,6-Difluorobenzylidene)amino)methyl)-4′-methylbiphenyl-3-yl

C21H16NCl2 :

3′-Chloro-2′-((4-chlorobenzyl)iminomethyl)–4-methyl-2-biphenyl

C21H17ClN:

5-Chloro-2-((((4′-methylbiphenyl-2-l)methyl)imino) methyl)phenyl

C22H20N:

3-Methyl-2-((((4′-methylbiphenyl-2-yl)methyl)imino) methyl)phenyl

C23H26O3P2 :

Diethyloxy(diphenylphosphino(phenyl)methyl)phosphonate

C24H24N:

3,5-Dimethyl-2-(((4′-methylbiphenyl-2-yl)methylimino)methyl)-benzyl

C29H29NP:

(2-(1-Dimethylamino)ethyl)-6-(2-(diphenylphosphino)-2-phenylvinyl)phenyl

C30H26AsOP:

(1α,4α,5α-)-4-(Diphenylarsino)-5-(diphenylphosphino)-7-oxabicyclo(2.2.1)hept-2-ene

C30H34N2P2 :

Ph2P(CH2)2P(Ph)2CHCH2NHNMe2

C40H36N2P2 :

{N(p-tolyl)=P(Ph2)}2CH2

mcpt:

[3-(Methylcarbamoyl)perhydropyrimidine.1-yl]methylimino-methanethiolate

2,6-Me2C5H3N:

2,6-Dimethylpyridine

NC10H9 :

2-Phenylpyridine

NC11H12 :

2-(4-Methylphenyl)pyridine

P(η 3-C6H12N3):

1,3,5-Triaza-7-phosphatricyclo[3.3.1.13,7]decane

(PhO)2POC6H4 :

2-((Diphenoxyphosphino)oxy)phenyl

Ph2P(C9H10N2O2):

2-(2-(Diphenylphosphino)phenyl)-4-isopropyl-1,3-oxazoline

Ph2P(CH2)2NMe2 :

Diphenyl(2-dimethylaminoethyl)phosphine

Ph2P(N2C7H4ClS):

6-Chloro-2-(diphenylphosphinamino)benzothiazole

Ph2P(N2C7H5):

1-(Diphenylphosphino)-7-azaindole

Ph2PC13H13N2 :

N-Benzyl-N-(diphenylphosphinomethyl)pyridin-2-amine

Ph2PC15H14N:

(1-Phenylethyl)-N-(2-diphenylphosphinobenzylidene)amine

Ph2PC22H23N2O:

2-(2-(Diphenylphosphino)phenylene)-4-(2-hydroxyphenyl)-7,8-dimethyl-2,3-dihydro-1H-1,5-benzodiazepine

Ph2PC7H7O:

2-(Diphenylphosphinato)phenoxymethyl

Ph2PCH2(C3H4NO):

(2-Oxazolin-2-ylmethyl)diphenylphosphine

\( { \Pr }_{2}^{{i}} {\text{PC}}_{11} {\text{H}}_{12} {\text{N}} \) :

2-(Dimethylamino)-1-(diisopropylphosphino)-3H-indine

tpitm:

(Thiophosphoranyl)(iminophospharanyl)methyl

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Acknowledgements

This work was supported by the Projects VEGA 1/0873/15, KEGA 022UK-4/2015, APVV-15-0585.

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Authors and Affiliations

  1. Department of Pharmaceutical Analysis and Nuclear Pharmacy, Faculty of Pharmacy, Comenius University in Bratislava, Odbojárov 10, 832 32, Bratislava, Slovak Republic

    Milan Melník & Peter Mikuš

  2. Toxicological and Antidoping Center, Faculty of Pharmacy, Comenius University in Bratislava, Odbojárov 10, 832 32, Bratislava, Slovak Republic

    Peter Mikuš

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Correspondence to Milan Melník.

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Melník, M., Mikuš, P. Organophosphines in PtPCOX (X = N, Cl, S), PtPCNX (X = Cl, S, Br, I, As) and PtPCClX (X = S, I, As) derivatives: structural aspects. Transit Met Chem 43, 367–376 (2018). https://doi.org/10.1007/s11243-018-0223-7

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