Deprotonation-Induced Enantioselective Aggregation and Deprotonation-Induced Ligand Rearrangement of Copper(II) Complexes Yield 1D Homochiral and Heterochiral Chains and a Cyclic Tetramer, Respectively

Shii, Yoshiki; Motoda, Yuri; Matsuo, T.; Kai, Fumiaki; Nakashima, Toshio; Tuchagues, J. P.; Matsumoto, Naohide

doi:10.1021/ic9813260

Cited by 65 publications

(32 citation statements)

References 32 publications

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“…Another interesting example of the aggregation of helical species was reported by Matsumoto et al He described a fascinating model for the assembly of the homochiral structure 36,37. The initial building block is a mononuclear CuL 26 complex containing two imidazole groups.…”

Section: Aggregation Of Oligonuclear Helicates – Chirality Translamentioning

confidence: 98%

“…In the presence of an equimolar ratio of base, one of the two imidazole groups loses a proton and functions as a hydrogen‐bond acceptor to connect with the neighboring protonated imidazole as a donor. For this to occur, the hydrogen bond between the imidazole group and the deprotonated imidazolate group in the two neighboring molecules is asymmetric, and the helicates are linked into a one‐dimensional helical chain with the chirality of the initial unit being translated from one to the other, and then extending to the whole helical chain 36. Similarly, the cobalt(III) complex with achiral tripodal‐type ligands consisting of three imidazole groups induces the chiralities of the C and A enantiomers,37 The hemideprotonated species [Co(H 1.5 L 27 )] 1.5+ functions as a self‐complementary chiral building block, generating equal numbers of protonated and deprotonated molecules by an acid–base reaction to form an extended 2D homochiral layer consisting of hexanuclear structures with trigonal void units (Figure 12).…”

Section: Aggregation Of Oligonuclear Helicates – Chirality Translamentioning

confidence: 99%

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Chirality Transfer through Helical Motifs in Coordination Compounds

Zhao

Guo

et al. 2007

Eur J Inorg Chem

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Helicates obtained by self‐assembly have initiated a revolution from classical coordination chemistry to extensive supramolecular concepts. The design of helicates will be described, and the structural features that are necessary for chirality transfer, as well as the extension of chirality from one‐dimensional to three‐dimensional chiral polymers in complicated chiral architectures will also be addressed. Chiralassembly by using achiral components has been given considerable attention in this review paper. The understanding of the essential processes and mechanisms in the chiral assembly on the basis of helicate supramolecular structures is a fundamental study in a variety of disciplines ranging from biology to materials science.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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Section: Aggregation Of Oligonuclear Helicates – Chirality Translamentioning

confidence: 98%

Section: Aggregation Of Oligonuclear Helicates – Chirality Translamentioning

confidence: 99%

Chirality Transfer through Helical Motifs in Coordination Compounds

Zhao

Guo

et al. 2007

Eur J Inorg Chem

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“…Metal complexes of Schiff bases have been extensively studied, and copper(II) complexes play a major role in both synthetic and structural research [1][2][3]. Schiff base metal complexes are one of the most important stereochemical models in transition metal coordination chemistry with their easy preparation and structural variation [4][5][6].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of dichloro ((N-(N ',N '- dimethylammonio) ethyl) - 2,4 - dichlorosalicylaldiminato-N ,O) copper(II) ,Cu(C11H14Cl2N2O) Cl2

Ma¹,

Wu²,

She³

et al. 2006

Zeitschrift Für Kristallographie - New Crystal Structures

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C11H14CI4CUN2O, orthorhombic, P2i2i2i (no. 19), a = 7.737(2) Ä, b = 10.131(2) Ä, c = 20.229(3) A, V = 1585.6 Ä 3 , Ζ = 4, Rp(F) = 0.040, wR^F*) = 0.079, Τ = 298 Κ. DiscussionMetal complexes of Schiff bases have been extensively studied, and copper(II) complexes play a major role in both synthetic and structural research [1][2][3]. Schiff base metal complexes are one of the most important stereochemical models in transition metal coordination chemistry with their easy preparation and structural variation [4][5][6]. As an extension of our work on the structural characterization of Schiff base complexes [7], a new mononuclear copper(II) complex is reported. The Cu n ion in the title complex is four-coordinated by one Ο and one imine Ν atom of the Schiff base, and by two terminal CI atoms, giving a tetrahedral environment. All the bond lengths related to the Cu center are comparable to the corresponding values observed in other Schiff base copper(II) complexes [8][9][10]. Source of material Reagents and solvents used were of commercially available quality. A^-Dimethylethane-1,2-diamine (44.3 mg, 0.5 mmol), 3,5-dichloro-2-hydroxybenzaldehyde (95.3 mg, 0.5 mmol), and CuCl 2 · 2H2O (85.2 mg, 0.5 mmol) were stirred and refluxed in ethanol at about 351 Κ for 1 h. Then the mixture was cooled to room temperature and filtered. Prismatic crystals suitable for Xray structural determination were formed by slow evaporation of the solvent from the filtrate after about a week. Elemental analysis: found -C, 33.23 %; H, 3.45 %; N, 7.17 %; calc. forC n Hi 4 Cl4CuN20-C, 33.40 %; H, 3.57%; N, 7.08 %.

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Section: Discussionmentioning

confidence: 99%

Crystal structure of dichloro((N-(N′,N′-dimethylammonio)ethyl)- 2,4-dichlorosalicylaldiminato-N,O)copper(II), Cu(C11H14Cl2N2O)Cl2

She

et al. 2006

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialReagents and solvents used were of commercially available quality. N,N-Dimethylethane-1,2-diamine (44.3 mg, 0.5 mmol), 3,5-dichloro-2-hydroxybenzaldehyde (95.3 mg, 0.5 mmol), and CuCl 2 · 2H2O (85.2 mg, 0.5 mmol) were stirred and refluxed in ethanol at about 351 K for 1 h. Then the mixture was cooled to room temperature and filtered. Prismatic crystals suitable for Xray structural determination were formed by slow evaporation of the solvent from the filtrate after about a week. Elemental analysis: found C, 33.23 %; H, 3.45 %; N, 7.17 %; calc. for C 11H14Cl4CuN2O C, 33.40 %; H, 3.57 %; N, 7.08 %. Experimental detailsAtom H2 was located in a Fourier difference map and refined isotropically, with the NH distance restrained to 0.90(1) Å. All other H atoms were positioned geometrically and constrained as riding atoms, with CH distances of 0.93 Å 0.97 Å and U iso(H) set to 1.2 or 1.5Ueq(C) of the parent atom. DiscussionMetal complexes of Schiff bases have been extensively studied, and copper(II) complexes play a major role in both synthetic and structural research [1][2][3]. Schiff base metal complexes are one of the most important stereochemical models in transition metal coordination chemistry with their easy preparation and structural variation [4][5][6]. As an extension of our work on the structural characterization of Schiff base complexes [7], a new mononuclear copper(II) complex is reported.The Cu II ion in the title complex is four-coordinated by one O and one imine N atom of the Schiff base, and by two terminal Cl atoms, giving a tetrahedral environment. All the bond lengths related to the Cu center are comparable to the corresponding values observed in other Schiff base copper(II) complexes [8][9][10].

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Deprotonation-Induced Enantioselective Aggregation and Deprotonation-Induced Ligand Rearrangement of Copper(II) Complexes Yield 1D Homochiral and Heterochiral Chains and a Cyclic Tetramer, Respectively

Cited by 65 publications

References 32 publications

Chirality Transfer through Helical Motifs in Coordination Compounds

Chirality Transfer through Helical Motifs in Coordination Compounds

Crystal structure of dichloro ((N-(N ',N '- dimethylammonio) ethyl) - 2,4 - dichlorosalicylaldiminato-N ,O) copper(II) ,Cu(C11H14Cl2N2O) Cl2

Crystal structure of dichloro((N-(N′,N′-dimethylammonio)ethyl)- 2,4-dichlorosalicylaldiminato-N,O)copper(II), Cu(C11H14Cl2N2O)Cl2

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