Influence of metal and ligand types on stacking interactions of phenyl rings with square-planar transition metal complexes
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In order to find out whether metal type influences the stacking interactions of phenyl rings in square-planar complexes, geometrical parameters for Cu, Ni, Pd and Pt complexes, with and without chelate rings, were analyzed and compared. By searching the Cambridge Structural Database, 220 structures with Cu complexes, 211 with Ni complexes, 285 with Pd complexes, and 220 with Pt complexes were found. The results show that the chelate ring has a tendency to make the stacking interaction with the phenyl ring independent of metal type in the chelate ring. However, there are some differences among metals for complexes without a chelate ring. There are a number of structures containing Pd and Pt complexes, without chelate rings, that have short carbon-metal distances and parallel orientations of the phenyl ring with respect to the coordination plane. It was found that some of these complexes have a common fragment, CN, as a part of the ligands. This indicates that the CN supports stacking interactions of square planar complexes with the phenyl ring. [...]
1 - 3 - 2007
1 - 3 - 2007
- Department of Chemistry, University of Belgrade, 11000, Belgrade, Serbia and Montenegro
- Laboratory of Theoretical Physics and Condensed Matter Physics, ‘Vinča’ Institute of Nuclear Sciences, 11001, Belgrade, Serbia and Montenegro
- Department of Chemistry, University of Belgrade, 11000, Belgrade, Serbia and Montenegro, email@example.com
-  K. Shibasaki, A. Fujii, N. Mikami and S. Tsuzuki: “Magnitude of the CH/π Interaction in the Gas Phase: Experimental and Theoretical Determination of the Accurate Interaction Energy in Benzene-methane”, J. Phys. Chem. A, Vol. 110, (2006), pp. 4397–4404. http://dx.doi.org/10.1021/jp0605909[Crossref]
-  Y. Li and C.M. Yang: “A Tryptophan-Containing Open-Chain Framework for Tuning a High Selectivity for Ca2+ and 13C NMR Observation of a Ca2+-Indole Interaction in Aqueous Solution”, J. Am. Chem. Soc., Vol. 127, (2005), pp. 3527–3530. http://dx.doi.org/10.1021/ja046517i[Crossref]
-  M. Nishio: “CH/π hydrogen bonds in crystals”, Cryst. Eng. Comm., Vol. 6, (2004), p. 130. [Crossref]
-  M. Nishio, M. Hirota and Y. Umezava: The CH/π Interaction, Evidence, Nature, and Conesequence, Wiley-VCH, New York, (1998).
-  E.V. Pletneva, A.T. Laederach, D.B. Fulton and N.M. Kostic: “The role of cation-π interactions in biomolecular association. Design of peptides favoring interactions between cationic and aromatic amino acid side chains”, J. Am. Chem. Soc., Vol. 123, (2001), pp. 6232–6245. http://dx.doi.org/10.1021/ja010401u[Crossref]
-  T.P. Burhardt, N.O. Juranić, S. Macura and K. Ajtai: “Cation-π interaction in a folded polypeptide”, Biopolymers, Vol. 63, (2002), pp. 261–272. http://dx.doi.org/10.1002/bip.10070[Crossref]
-  S. Yanagisawa, K. Sato, M. Kikuchi, T. Kohzuma and C. Dennison: “Introduction of a π - π Interaction at the Active Site of a Cupredoxin: Characterization of the Met16Phe Pseudoazurin Mutant”, Biochemistry, Vol. 42, (2003), pp. 6853–6862. http://dx.doi.org/10.1021/bi030030p[Crossref]
-  E. A. Meyer, R. K. Castellano, F. Diederich: “Interactions with aromatic rings in chemical and biological recognition”, Angew. Chem. Int. Ed., Vol. 42, (2003), pp. 1210–1250. http://dx.doi.org/10.1002/anie.200390319[Crossref]
-  O. Yamauchi, A. Odani and M. Takani: “Metal-amino acid chemistry. Weak interactions and related functions of side chain groups”, J. Chem. Soc. Dalton Trans., (2002), pp. 3411–3421. [Crossref]
-  W. Schmitt, C.E. Anson, J.P. Hill and A.K. Powell: “Cation-π Binding of an Alkali Metal Ion by Pendant α,α-Dimethylbenzyl Groups within a Dinuclear Iron(III) Structural Unit”, J. Am. Chem. Soc., Vol. 125, (2003), pp. 11142–11143. http://dx.doi.org/10.1021/ja029409+[Crossref]
-  T. Lovell, F. Himo, W.G. Han and L. Noodleman: “Density functional methods applied to metalloenzymes”, Coord. Chem. Rev., Vol. 238, (2003), pp. 211–232. http://dx.doi.org/10.1016/S0010-8545(02)00331-4[Crossref]
-  W.L. Zhu, X.J. Tan, J.H. Shen, X.M. Luo, F. Chen, P.C. Mok, R.Y. Ji, K.X. Chen and H.L. Jiang: “Differentiation of Cation-π Bonding from Cation-π Intermolecular Interactions: A Quantum Chemistry Study Using Density-Functional Theory and Morokuma Decomposition Methods”, J. Phys. Chem. A., Vol. 107, (2003), pp. 2296–2303. http://dx.doi.org/10.1021/jp0270598[Crossref]
-  T.D. Vaden and J. M. Lisy: “Characterization of hydrated Na+(phenol) and K+(phenol) complexes using infrared spectroscopy”, J. Chem. Phys.A., Vol. 120, (2004), pp. 721–730.
-  S.D. Zarić: “Metal ligand-aromatic cation-π interactions”, Eur. J. Inorg. Chem., (2003), pp. 2197–2209.
-  S.D. Zarić, D. Popović and E.W. Knapp: “Metal ligand aromatic cation-π interactions in metalloproteins: ligands coordinated to metal interact with aromatic residues”, Chem. Eur. J., Vol. 6, (2000), pp. 3935–3942. http://dx.doi.org/10.1002/1521-3765(20001103)6:21<3935::AID-CHEM3935>3.0.CO;2-J[Crossref]
-  S.D. Zarić: “Cation-π interaction with transition-metal complex as cation”, Chem. Phys. Lett., Vol. 311, (1999), pp. 77–80. http://dx.doi.org/10.1016/S0009-2614(99)00805-2[Crossref]
-  M. Milčić and S.D. Zarić: “Intramolecular metal ligand aromatic cation-π interactions in crystal structures of transition metal complexes”, Eur. J. Inorg. Chem., (2001), pp. 2143–2150.
-  M.K. Milčić, Z.D. Tomić and S.D. Zaric: “Very strong metal ligand aromatic cation-π interactions in transition metal complexes: intermolecular interaction in tetraphenylborate salts”, Inorg. Chim. Acta, Vol. 357, (2004), pp. 4327–4329. http://dx.doi.org/10.1016/j.ica.2004.06.019[Crossref]
-  M.K. Milčić, V.B. Medaković, D.N. Sredojević, N.O. Juranić and S.D. Zarić: “Electron delocalization mediates the metal-dependent capacity for CH/π interactions of acetylacetonato chelates”, Inorg. Chem., Vol. 45, (2006), pp. 4755–4763. http://dx.doi.org/10.1021/ic051926g[Crossref]
-  H. Tsubaki, S. Tohyama, K. Koike, H. Saitoh and O. Ishitani: “Effect of intramolecular π-π and CH-π interactions between ligands on structure, electrochemical and spectroscopic properties of fac-[Re(bpy) (CO)3(PR3)] + (bpy = 2,2’-bipyridine; PR3 = trialkyl or triarylphosphines)”, Dalton Trans., Vol. 2, (2005), pp. 385–395.
-  H. Kumita, T. Kato, K. Jitsukawa, H. Einaga and H. Masuda: “Characterization of an NH-π Interaction in Co(III) Ternary Complexes with Aromatic Amino Acids”, Inorg. Chem., Vol. 40, (2001), pp. 3936–3942. http://dx.doi.org/10.1021/ic000990p[Crossref]
-  H. Suezawa, T. Yoshida, Y. Umezawa, S. Tsuboyama and M. Nishio: “CH/π interactions implicated in the crystal structure of transition metal compounds-a database study”, Eur. J. Inorg. Chem., (2002), pp. 3148–3155.
-  G.A. Bogdanović, A.S. Biré and S.D. Zarić: “Evidence based on crystal structures and calculations of a C-H...π interaction between an organic moiety and a chelate ring in transition metal complexes”, Eur. J. Inorg. Chem., (2002), pp. 1599–1602.
-  V.B. Medaković, M.K. Milčić, G.A. Bogdanović and S.D. Zarić: “C-H...π interactions in the metal-porphyrin complexes with chelate ring as the H acceptor”, J. Inorg. Biochemistry., Vol. 98, (2004), pp. 1867–1873. http://dx.doi.org/10.1016/j.jinorgbio.2004.08.012[Crossref]
-  V. Philip, V. Suni, M.R.P. Kurup and M. Nethaji: “Structural and spectral studies of nickel(II) complexes of di-2-pyridyl ketone N4,N4-(butane-1,4-diyl)thiosemicarbazone”, Polyhedron., Vol. 23, (2004), pp. 1225–1233. http://dx.doi.org/10.1016/j.poly.2004.02.004[Crossref]
-  Z.D. Tomić, S.B. Novaković and S.D. Zarić: “Intermolecular interactions between chelate rings and phenyl rings in square-planar copper(II) complexes”, Eur. J. Inorg. Chem., (2004), pp. 2215–2218.
-  Z.D. Tomić, D.N. Sredojević and S.D. Zarić: “Stacking interactions between chelate and phenyl ring in square-planar transition metal complexes”, Crystal Growth & Design., Vol 6, (2005), pp. 29–31.
-  A. Castineiras, A.G. Sicilia-Zafra, J.M. Gonzáles-Pérez, D. Choquesillo-Lazarte and J. Niclós-Gutiérrez: “Intramolecular ”Aryl-metal chelate ring” π,π-interactions as structural evidence for metalloaromaticity in (aromatic alpha,alpha’-diimine)-copper(II) chelates: molecular and crystal structure of aqua(1,10-phenanthroline)(2-benzylmalonato)copper(II) three-hydrate”, Inorg. Chem., Vol. 41, (2002), pp. 6956–6958. http://dx.doi.org/10.1021/ic026004h[Crossref]
-  E. Craven, C. Zhang, C. Janiak, G. Rheinwald and H. Lang: “Synthesis, structure and solution chemistry of (5,5’-dimethyl-2,2’-bipyridine) (IDA)copper(II) and structural comparison with aqua(IDA)(1,10-phenanthroline)copper(II) (IDA = iminodiacetato)”, Zeitsch. Anorg. Allgem. Chem., Vol. 629, (2003), pp. 2282–2290. http://dx.doi.org/10.1002/zaac.200300223[Crossref]
-  U. Mukhopadhyay, D. Choquesillo-Lazarte, J. Niclós-Gutiérrez and I. Bernal: “A critical look on the nature of the intra-molecular interligand π,π-stacking interaction in mixed-ligand copper(II) complexes of aromatic side-chain amino acidates and α,α’-diimines”, Cryst. Eng. Comm., Vol. 6, (2004), pp. 627–632. [Crossref]
-  H. Masui: “Metalloaromaticity”, Coord. Chem. Rev., Vol. 219–221, (2001), pp. 957–992. http://dx.doi.org/10.1016/S0010-8545(01)00389-7[Crossref]
-  F.H. Allen: ”The Cambridge Structural Database: a quarter of a million crystal structures and rising”, Acta Crystallogr. B, Vol. 58, (2002), pp. 380–388. http://dx.doi.org/10.1107/S0108768102003890[Crossref]
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