Abstract
Reaction of [PdCl2(PPh3)2] with imidazolidine-2-thione {SC3H4(NH)2}in the presence of triethylamine involved activation of N–H bonds and formed an unusual oxo-bridged dianion, (SC3H4N2–O–N2C3H4S) 2− coordinated to Pd II in Pd{κ 3–S, O, S–(SC3H4N2–O–N2C3H4S)}(PPh3)] ⋅CH3CN 1, which has been studied using elemental analysis, IR, NMR, X-ray crystallography and ESI-mass studies.
Similar content being viewed by others
References
Raper E S 1996 Complexes of heterocyclic thionates.1. Complexes of monodentate and chelating ligands Coord. Chem. Rev. 153 199
Raper E S 1997 Complexes of heterocyclic thionates. Part 2. Complexes of bridging ligands Coord. Chem. Rev. 165 475
Garcia-Vazquez J A, Romero J and Sousa A 1999 Electrochemical synthesis of metallic complexes of bidentate thiolates containing nitrogen as an additional donor atom Coord. Chem. Rev. 193–195 691
Nakatsu Y, Nakamura Y, Matsumoto K and Ooi S 1992 Synthesis and solution behavior of mononuclear palladium(II) and platinum(II) complexes containing pyridine-2-thiolate as a ligand. Crystal structure of chloro (pyridine-2thiolato)(triphenylphosphine)palladium(II) Inorg. Chim. Acta 196 81
Lobana T S, Verma R, Hundal G and Castineiras A 2000 Metal-heterocyclic thione interactions-12. Heterocyclic-2-thiolates platinum(II)/ palladium(II): the crystal structures of first examples of cis-[M(η 1-S-pyridine-2-thiolato)2(L–L)] {M = Pt, Pd, L–L = 1, 2-bis(diphenyl phosphino)ethane, M = Pt, L–L = 1,2-bis(diphenylphosphino)ethene}complexes containing pendant pyridyl groups Polyhedron 19 899
Galan R F, Manzano B R, Otero A, Poujaud N and Kubicki M 1999 Synthesis and characterization of new allyl palladium complexes with thionate ligands; X-ray molecular structures of [Pd3(η 3–C4H7)3 {pm(Me)2S}2](CF3 SO 3) and [Pd{ pm(Me)2S}2], η 3–C4H7 = η 3–2–MeC3H4, pm(Me)2S = Pyridine-4,6-dimethyl-2-thionate J. Organomet. Chem. 579 321
Padilla E M, Yamamoto J W and Jensen C M 1990 Isolation of palladium(lI) quinoline-2-thione (HqnS) and quinoline-2-thiolate (qnS) complexes: Crystal structures of Pd(HqnS)(PMe3)Cl2, [Pd(HqnS)2(PMe3)Cl][Cl] and vic-Pd2(μ, N−S η 2–qnS)2(η 1–qnS)2(PMe3 )2 Inorg. Chim. Acta 174 209
Lobana T S, Sultana R, Hundal G and Castineiras A 2009 Synthesis and crystal structures of polynuclear complexes of Cu I with 1-methyl-1, 3-imidazoline-2-thione Polyhedron 28 1573
Lobana T S, Kaur P J, Castineiras A, Turner P and Failes T W 2008 Synthesis, crystal and molecular structures of isomorphic N, S-bridged [Cu2(μ 2–I)2(PPh3)2 (μ 2–N,S–pymSH)] Dimer and S-bonded [CuX(η 1–S–pymSH)(PPh3)2] monomers (X = Cl, Br) Struct. Chem. 19 727
Lobana T S, Renu S., Hunda G and Butcher R J 2006 Synthesis of 1D {Cu6(μ 3–SC3H6N2)4(μ–SC3H6N2)2(μ–I)2 I 4}n and 3D {Cu2(μ–SC3H6N2)2(μ–SCN)2}n polymers with 1, 3-imidazolidine-2-thione: Bond isomerism in polymers Inorg. Chem. 45 9402
Lobana T S, Rohit S. and Butcher R J 2008 Pyridine-2-thione (pySH) derivatives of silver(I): Synthesis and crystal structures of dinuclear [Ag2 X 2(μ–S–pySH)2(PPh3)2] complexes (X = Cl, Br) Polyhedron 27 1375
Lobana T S and Castineiras A 2002 Metal-heterocyclic thione interactions. 13. Pyridine-2-thione derivatives of copper(I): Crystal structure of dinuclear [bromo (pyridine-2-thione)(tri-p-tolylphosphine)copper(I)]2complex Polyhedron 21 1603
Butler L M, Creighton J R, Oughtred R E and Raper E S 1983 Preparation, characterisation and crystal structure of dichloro tetrakis-(1-methylimidazoline-2(3H)-thione)palladium(II) dehydrate Inorg. Chim. Acta 75 149
Lobana T S, Kaur P J, Hundal G, Butcher R J and Castineiras A 2008 Variable bonding modes of pyrimidine-2-thione in PdII/PtII complexes [M(η 2–N, S–pymS)(η 1–S–pymS)(PPh3)] and [M(η 1–S–pymS)2 (L–L)] (L–L = dppm, dppe) Z. Anorg. Allg. Chem. 634 747
Nakatsu Y, Nakamura Y, Matsumoto K and Ooi S 1992 Synthesis and solution behavior of mononuclear palladium(II) and platinum(II) complexes containing pyridine-2-thiolate as a ligand. Crystal structure of chloro (pyridine-2-thiolato)-(triphenylphosphine)palladium(II) Inorg. Chim. Acta 196 81
Umakoshi K, Kinoshita I and Ooi S 1987 Dinuclear palladium(II) complex of pyridine-2-thiol Inorg. Chim. Acta 127 L41
Umakoshi K, Ichimura A, Kinoshita I and Ooi S 1990 The dinuclear palladium(II) complex of pyridine-2-thiol. Synthesis, structure, and electrochemistry Inorg. Chem. 29 4005
Mendia A, Cerrada E, Arnaiz F J and Languna M 2006 Pyridine-2-thionate as a versatile ligand in Pd(II) and Pt(II) chemistry: The presence of three different co-ordination modes in [Pd2(μ 2– S, N–C5H4SN)(κ 2– μ 2–S–C5H4SN)(κ 2–dppm)(S–C5H4SN)2] Dalton Trans. 609
Brendler E, Wachtler E, Heine T, Zhechkov L, Langer T, Pottgen R, Hill A F and Wagler J 2011 Stannlyene or metallastanna(IV)octane: A matter of formalism Angew Chem. Int. Eng. Ed. 50 4696
Pons J, García-Antón J, Solans X, Font-Bardia M and Ros J 2008 Trans-dichloridobis(triphenylphosphine) palladium(II) Acta Cryst. E 64 m621
Altomare A, Cascarano G, Giacovazzo C and Guagliardi A 1993 Completion and refinement of crsytal structures with SIR 92 J. Appl. Crystallogr. 26 343
Sheldrick G M 2008 A short history of SHELX Acta Cryst. A 64 112
Acknowledgements
One of us (AKB) thanks the – Indian Academy of Sciences (Bangalore), National Academy of Sciences (Allahabad) and Indian National Science Academy (New Delhi) for a Summer Fellowship. Financial assistance from the Council of Scientific and Industrial Research (CSIR), New Delhi, in the form of Emeritus Scientist Grant [21(0904)/12-EMR-II] to T.S. Lobana, is gratefully acknowledged.
Author information
Authors and Affiliations
Corresponding author
Additional information
Supplementary Information (SI)
Crystallographic data (excluding structure factors) for the structure in this paper have been deposited with the Cambridge Crystallographic Data Centre, CCDC, 12 Union Road, Cambridge CB21EZ, UK. Copies of the data can be obtained free of charge on quoting the depository numbers CCDC number: 784651 or 1 (Fax: + 44-1223-336-033; E-Mail: deposit@ccdc.cam.ac.uk, http://www.cam.ac.uk).
Rights and permissions
About this article
Cite this article
MEHRA, V., BAINS, A.K., HUNDAL, G. et al. Transformation of 1,3-imidazolidine-2-thione (SC3H6N2) into (SC3H4N2–O–N2C3H4S)2− dianion chelated in [Pd{κ 3–S, O, S–(SC3H4N2–O–N2C3H4S)}(PPh3)]⋅CH3CN. J Chem Sci 129, 359–363 (2017). https://doi.org/10.1007/s12039-017-1242-1
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12039-017-1242-1