New Macrocyclic Ligands. XIV. Synthesis and X-Ray Structures of Potentially Pentadentate Ligands Incorporating Non-Symmetrically Arranged N4S-, N3OS-, N2O2S- and N2S2O-Heteroatoms

Baldwin, Darren S.; Bowden, BF; Duckworth, Paul A.; Lindoy, Leonard F.; McCool, Brian J.; Meehan, George V.; Vasilescu, Ioana M.; Wild, S. Bruce

doi:10.1071/ch02121

Cited by 7 publications

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“…The unsymmetrical 17-membered macrocycles 1 (SO/NNN), 2 (SO/NON), 3 (SO/NSN), 4 (SN/NNN) and 7 (ON/NNN) have been reported previously by our group 12 while the remainder of the series, 5 (SN/NON), 6 (SN/NSN), 8 (ON/NON) and 9 ON/NSN), are new and serve to complete the 'matrix' of 17membered macrocyclic ligands of this type. The preparations in each case involved a double Schiff-base condensation between the appropriate linear diamine derivative and the corresponding unsymmetrical dialdehyde precursor, followed by in situ reduction of the resulting diimine with sodium borohydride.…”

Section: Macrocycle Synthesis and Characterisationmentioning

confidence: 53%

“…The structures of 4 (SN/NNN), and 7 (ON/NNN), reported previously, also adopt quite related non-folded conformations. 12 In general, there is close agreement between bond lengths and angles of chemically equivalent bonds across all structures. 17) A ˚slightly exceeds the sum of the covalent radii 28 of octahedral Ni(II) (1.39 A ˚) and O (0.66 A ˚) however, it is comparable to the mean literature value of 2.15 A ˚for this bond type.…”

Section: Macrocycle Synthesis and Characterisationmentioning

confidence: 74%

“…7) is comprised of the 1,4,7-triazaheptane macrocyclic fragment and a chloro ligand in an equatorial fashion, while the second chloro ligand occupies an axial position in a distorted square pyramidal coordination geometry (see below). In contrast to the solid state structure of free 7, 12 the macrocyclic ring is folded in this complex and coordinates in an exo manner such that the copper ion is not contained in the macrocyclic cavity. The Cu-N bond distances are unexceptional (mean value 2.0394 A ˚).…”

Section: Macrocycle Synthesis and Characterisationmentioning

confidence: 85%

“…The macrocycle precursor dialdehydes 2-(2-(2-formylphenoxy)ethylthio)benzaldehyde, 2-(2-(2-formylphenylamino)ethylthio)benzaldehyde and 2-(2-(2-formylphenoxy)ethylamino)benzaldehyde incorporating SO-, SN-and ON-donor sequences were prepared as described previously. 12 Samples for elemental analysis were dried over silica gel in a vacuum. Crystals were used directly for the X-ray diffraction studies after removal from the crystallisation solution.…”

Section: Introductionmentioning

confidence: 99%

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Interaction of Co(ii), Ni(ii) and Cu(ii) with dibenzo-substituted macrocyclic ligands incorporating both symmetrically and unsymmetrically arranged N, O and S donors

et al. 2011

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The synthesis and characterisation of four 17-membered, dibenzo-substituted macrocyclic ligands incorporating unsymmetrical arrangements of their N 3 S 2 , N 3 O 2 and N 3 OS (two ligands) donor atoms are described; these rings complete the matrix of related macrocyclic systems incorporating both symmetric and unsymmetric donor sets reported previously. The X-ray structures of three of the new macrocycles are reported. In two of the Cu(II) structures only three of the possible five donor atoms present in the corresponding macrocyclic ligand bind to the Cu(II) site, whereas all five donors are coordinated in each of the remaining complexes. The interaction of Co(II), Ni(II) and Cu(II) with the unsymmetric macrocycle series has been investigated by potentiometric (pH) titration in 95% methanol; X-ray structures of two nickel and three copper complexes of these ligands, each exhibiting 1 : 1 (M : L) ratios, have been obtained. The results are discussed in the context of previous results for these metals with the analogous 17-membered ring systems incorporating symmetrical arrangements of their donor atoms, with emphasis being given to both the influence of the donor atom set, as well as the donor atom sequence, on the nature of the resulting complexes.

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Section: Macrocycle Synthesis and Characterisationmentioning

confidence: 53%

Section: Macrocycle Synthesis and Characterisationmentioning

confidence: 74%

Section: Macrocycle Synthesis and Characterisationmentioning

confidence: 85%

Section: Introductionmentioning

confidence: 99%

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Interaction of Co(ii), Ni(ii) and Cu(ii) with dibenzo-substituted macrocyclic ligands incorporating both symmetrically and unsymmetrically arranged N, O and S donors

et al. 2011

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“…The synthesis and characterisation of macrocycles 1-18 have been described previously (2,3). Samples for microanalysis were dried over silica gel in vacuum.…”

Section: Generalmentioning

confidence: 99%

Comparative investigation of the interaction of Zn(II), Cd(II), Ag(I) and Pb(II) with dibenzo-substituted macrocyclic ligands incorporating both symmetrically and unsymmetrically arranged N, O and S donors: synthetic, solution and X-ray studies

Vasilescu

Bourne

Clegg

et al. 2012

Supramolecular Chemistry

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Comparative investigation of the interaction of Zn(II), Cd(II), Ag(I) and Pb(II) with dibenzo-substituted macrocyclic ligands incorporating both symmetrically and unsymmetrically arranged N, O and S donors: synthetic, solution and X-ray studies, Supramolecular Chemistry, 24:8, 572-584, A comparison of the interaction of Zn(II), Cd(II), Ag(I) and Pb(II) with a matrix of 18, 17-membered, dibenzo-substituted macrocyclic ligands (1-18) incorporating nitrogen, oxygen and/or sulfur heteroatom sites that share the same carbon backbone is reported. Potentiometric log K data for complexes of these metals with 5, 6, 8 and 9 incorporating unsymmetric arrangements of their donor sets were obtained and the results compared with previously determined stability data for the remaining symmetrical and unsymmetrical ligand complexes forming the above matrix. Structure -function relationships underlying the relative magnitudes of the respective log K values are discussed, with emphasis given to the influence of both the donor atom set and the donor atom sequence on the nature of the resulting complexes. The X-ray structures of [CdL(NO 3 )] (NO 3 )·CH 3 CH 2 OH (L ¼ 4, SN 4 donor set), [CdL(NO 3 ) 2 ]·CH 3 OH (L ¼ 7, ON 4 donor set), [AgL]PF 6 (L ¼ 4, SN 4 donor set) and [AgL]PF 6 (L ¼ 9, OSN 3 donor set) are presented along with that of the metal-free diprotonated nitrate salt (LH 2 )(NO 3 ) 2 (L ¼ 6, S 2 N 3 donor set).

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Metallkomplexe mit N₂O₂S₂‐Koordinationssphäre. Synthese und Charakterisierung der Cobalt(II)‐, Nickel(II)‐ und Kupfer(II)‐Komplexe eines 15‐ und eines 16‐gliedrigen N, N′‐bis(2‐hydroxyethyl)‐funktionalisierten makrocyclischen Liganden

Mattes

Mühlenbrock

Leeners

et al. 2004

Zeitschrift anorg allge chemie

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Die makrocyclischen Liganden 6, 10‐Bis(2‐hydro‐xyethyl)‐7, 8, 9, 11, 17, 18‐hexahydro‐dibenzo‐[e, n][1, 4, 8, 12]‐dithiadiaza‐cyclopentadecin (1) (L1) und 5, 13‐Bis(2‐hydroxyethyl)‐7, 8, 9, 10, 16, 17, 18, 19, 20‐nonahydro‐dibenzo‐[g, o][1, 9, 5, 13]‐dithiadiaza‐cyclohexadecin (L4) sowie ihre Nickel(II)‐, Cobalt(II)‐ und Kupfer(II)‐Komplexe wurden hergestellt und durch Röntgenstrukturanalysen charakterisiert. In allen Komplexen haben die Metallionen eine oktaedrische N2O2S2‐Koordinationssphäre. Durch Faltung der Liganden um die N···M···S‐Achse bzw. um die N···M···N′‐Achse resultiert eine all‐cis‐Konfiguration für die Komplexe von L1 und eine trans‐N2‐cis‐O2‐cis‐S2‐Konfiguration für die Komplexe von L4. Der Cobalt(II)‐Komplex [CoL1(‐H)CoL1](ClO4)3 (2) ist dimer. Die Verknüpfung erfolgt über eine kurze Wasserstoffbrückenbindung der Länge 2.402(12)Å. Die Kupfer(II)‐Komplexe von L1 und L4 unterscheiden sich im Hinblick auf die Jahn‐Teller‐Verzerrung.

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New Macrocyclic Ligands. XIV. Synthesis and X-Ray Structures of Potentially Pentadentate Ligands Incorporating Non-Symmetrically Arranged N4S-, N3OS-, N2O2S- and N2S2O-Heteroatoms

Cited by 7 publications

References 1 publication

Interaction of Co(ii), Ni(ii) and Cu(ii) with dibenzo-substituted macrocyclic ligands incorporating both symmetrically and unsymmetrically arranged N, O and S donors

Interaction of Co(ii), Ni(ii) and Cu(ii) with dibenzo-substituted macrocyclic ligands incorporating both symmetrically and unsymmetrically arranged N, O and S donors

Comparative investigation of the interaction of Zn(II), Cd(II), Ag(I) and Pb(II) with dibenzo-substituted macrocyclic ligands incorporating both symmetrically and unsymmetrically arranged N, O and S donors: synthetic, solution and X-ray studies

Metallkomplexe mit N₂O₂S₂‐Koordinationssphäre. Synthese und Charakterisierung der Cobalt(II)‐, Nickel(II)‐ und Kupfer(II)‐Komplexe eines 15‐ und eines 16‐gliedrigen N, N′‐bis(2‐hydroxyethyl)‐funktionalisierten makrocyclischen Liganden

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New Macrocyclic Ligands. XIV. Synthesis and X-Ray Structures of Potentially Pentadentate Ligands Incorporating Non-Symmetrically Arranged N4S-, N3OS-, N2O2S- and N2S2O-Heteroatoms

Cited by 7 publications

References 1 publication

Interaction of Co(ii), Ni(ii) and Cu(ii) with dibenzo-substituted macrocyclic ligands incorporating both symmetrically and unsymmetrically arranged N, O and S donors

Interaction of Co(ii), Ni(ii) and Cu(ii) with dibenzo-substituted macrocyclic ligands incorporating both symmetrically and unsymmetrically arranged N, O and S donors

Comparative investigation of the interaction of Zn(II), Cd(II), Ag(I) and Pb(II) with dibenzo-substituted macrocyclic ligands incorporating both symmetrically and unsymmetrically arranged N, O and S donors: synthetic, solution and X-ray studies

Metallkomplexe mit N2O2S2‐Koordinationssphäre. Synthese und Charakterisierung der Cobalt(II)‐, Nickel(II)‐ und Kupfer(II)‐Komplexe eines 15‐ und eines 16‐gliedrigen N, N′‐bis(2‐hydroxyethyl)‐funktionalisierten makrocyclischen Liganden

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About

Metallkomplexe mit N₂O₂S₂‐Koordinationssphäre. Synthese und Charakterisierung der Cobalt(II)‐, Nickel(II)‐ und Kupfer(II)‐Komplexe eines 15‐ und eines 16‐gliedrigen N, N′‐bis(2‐hydroxyethyl)‐funktionalisierten makrocyclischen Liganden