Copper(II) complexes of 3,3′-annelated 2,2′-bi[1,8]naphthyridine

Draux, Madeleine; Bernal, Ivan; Lefoulon, François; Thummel, Randolph P.

doi:10.1016/s0020-1693(00)86772-9

Cited by 10 publications

(6 citation statements)

References 33 publications

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“…with a dz2 groundstate for Cu 2+. The fact that the water molecule coordinates equatorially, however, is not in accordance with the theoretical predictions of Rossi & Hoffmann (1975) for the coordination site of highly electronegative atoms and in this respect it differs from the CuNzCI20 chromophore mentioned above (Draux, Bernal, Lefoulon & Thummel, 1985). However, because our ligand is monodentate there is no steric reason to force the two N atoms into a cis orientation, and the most important origin is likely to be the intermolecular hydrogen bonding system.…”

Section: -928(5)contrasting

confidence: 59%

“…Five-coordinate CuN2BrzO chromophores reported in the literature are distorted-tetragonal: even trigonal CuNzC120 chromophores are scarce. A related trigonal compound is aquadichloro-3,3'-dimethylene-2,2'-bis(1,8-naphthyridine)copper(II) (Draux, Bernal, Lefoulon & Thummel, 1985), in which the axial donor N and O atoms are at distances of 2-005 (7) and 2-019 (6)•, respectively, and the equatorial donors are two CI atoms at 2.287 (2) and 2.291 (2), and an N atom at 2.243 (7)/1. McKenzie, 1978;Veldhuis, Driessen & Reedijk, 1986).…”

Section: -928(5)mentioning

confidence: 99%

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Structure of aquadibromobis(1,2,4-triazolo[1,5-a]pyrimidine-N3)copper(II), a one-dimensional alternating copper(II). oxygen array

Albada¹,

Graaff²,

Haasnoot³

et al. 1991

Acta Crystallogr C

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946[CuBr2(CIaHIsN3)] 2.177, gll = 2-065) and remains unchanged over the temperature range 298-4.2 K. The reflectance electronic spectrum shows, in the visible region, one broad and unresolved band centred about 12000 cm -1. These spectroscopic results are consistent with a geometry around the copper(II) ion near to trigonal bipyramidal (Reinen & Friebel, 1984; Hathaway & Billing, 1970), in good agreement with the crystal structure of the complex.

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Section: -928(5)contrasting

confidence: 59%

Section: -928(5)mentioning

confidence: 99%

Structure of aquadibromobis(1,2,4-triazolo[1,5-a]pyrimidine-N3)copper(II), a one-dimensional alternating copper(II). oxygen array

Albada¹,

Graaff²,

Haasnoot³

et al. 1991

Acta Crystallogr C

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“…Unlike the biisoquinoline ligands, most 2,2‘-bipyridine ligands, and similar derivatives, form complexes in which the aromatic rings are coplanar, to maximize orbital overlap with the metal . Despite the difficulty associated with the synthesis of enantiopure bipyridines, the use of such ligands in asymmetric catalysis has been reported. − The asymmetry of these bipyridyl ligands is almost always due to stereogenic centers remote from the metal binding site; , however, some chiral bipyridine ligands with chiral axes have been reported. ,,− Certain 3,3‘-annelated 2,2‘-bipyridines, biquinolines, and related derivatives, ,− as well as 3-substituted and 3,3‘-disubstituted 2,2‘-bipyridines, ,,,− have skewed conformations in the unbound and bound forms (Figure ). The barrier to atropisomerization in the annelated derivatives is controlled by the length and substitution pattern of the tether.…”

Section: 2 Atropisomeric Biisoquinolines and Bipyridinesmentioning

confidence: 99%

“…[263][264][265][266][267][268][269][270] The asymmetry of these bipyridyl ligands is almost always due to stereogenic centers remote from the metal binding site; 271,272 however, some chiral bipyridine ligands with chiral axes have been reported. 263,264,[272][273][274] Certain 3,3′-annelated 2,2′-bipyridines, biquinolines, and related derivatives, 263,[275][276][277][278][279][280][281][282][283][284][285][286][287][288][289][290][291] as well as 3-substituted and 3,3′-disubstituted 2,2′bipyridines, 248,257,289,[292][293][294][295] have skewed conformations in the unbound and bound forms (Figure 65). The barrier to atropisomerization in the annelated derivatives is controlled by the length and substitution pattern of the tether.…”

Section: Atropisomeric Biisoquinolines and Bipyridinesmentioning

confidence: 99%

Use of Achiral and Meso Ligands To Convey Asymmetry in Enantioselective Catalysis

2003

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1. Introduction and Scope 3297 2. The Use of Achiral Salen Ligands in Asymmetric Catalysis 3305 3. Use of Achiral Biphenol-Based Ligands in Asymmetric Catalysis 3308 3.1. Asymmetric Carbonyl−Ene Reaction 3308 3.2. Asymmetric Addition of Methyl Groups to Aldehydes 3309 3.3. Asymmetric Baeyer−Villiger Oxidation 3309 4. Atropisomeric Biphenyl-Based Phosphines and Related Ligands in Asymmetric Catalysis 3310 4.1. Asymmetric Hydrogenation Reactions Using BIPHEP-Derived Ligands 3311 4.2. Asymmetric Diels−Alder and Carbonyl−Ene Reactions with BIPHEP-Derived Ligands 3313 4.3. Interconversion of Diastereomeric Catalysts and Catalyst Precursors Containing BIPHEP Derivatives 3315 4.4. Mechanistic Aspects of Atropisomerization of BIPHEP 3317 4.5. A Potentially Useful New Class of Achiral Diphosphine Ligands (NUPHOS) 3319 4.6. Complexes of a Meso Cyclohexane-Based Diphosphine 3320 4.7. Spontaneous Resolution of an Asymmetric Catalyst Bearing a Bis(phosphole) Ligand 3320 4.8. A Metallocene Catalyst with a Biphenyl Backbone 3322 4.9. Use of Bis(diphenylphosphino)ferrocene and Related Ligands in Asymmetric Catalysis 3323 4.10. Dynamic Resolution of Bis(phospholyl)−Zr Complexes 3325 5. Examination of the Barrier to Atropisomerization in Biphenyl-Based Diamines 3326

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“…It became of interest to extend this bridging concept to other nuclei besides pyridine, and we have similarly examined analogous derivatives of 2,2‘-biquinoline, 2,2‘-bi[1,8]naphthyridine, and 2,2‘-biimidazole . In each of these cases, the chelating site involved two azaaryl rings joined by a 2,2‘- bond.…”

Section: Introductionmentioning

confidence: 99%

Cu(I) Complexes of 3,3‘-Polymethylene Bridged Derivatives of 2,2‘-Bi-1,10-Phenanthroline

Riesgo

Thummel

2003

Inorg. Chem.

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A series of 3,3'-polymethylene-2,2'-bi-1,10-phenanthrolines coordinate with Cu(I) to form dinuclear complexes [(CuL)(2)](2+). As the 3,3'-bridge is lengthened from two to four carbons, the ligand becomes more twisted about the 2,2'-bond, favoring dinuclear coordination. The distance between the two copper atoms varies from 2.92 A for the dimethylene-bridged system to 3.59 A for the tetramethylene bridge. Favorable pi-stacking interactions occur between opposing ligands and promote complex formation. Competition experiments indicate that self-recognition is important and only homoleptic complexes are observed. Under equilibrium conditions, formation of the tetramethylene-bridged complex appears to be the most favored while the dimethylene-bridged system is least favored. The intensity of the long wavelength metal-ligand charge-transfer absorption band decreases as the 3,3'-bridge is shortened. Interaction between the two copper centers is evidenced by a splitting of the oxidation wave, and this splitting increases as the Cu-Cu distance is decreased.

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Copper(II) complexes of 3,3′-annelated 2,2′-bi[1,8]naphthyridine

Cited by 10 publications

References 33 publications

Structure of aquadibromobis(1,2,4-triazolo[1,5-a]pyrimidine-N3)copper(II), a one-dimensional alternating copper(II). oxygen array

Structure of aquadibromobis(1,2,4-triazolo[1,5-a]pyrimidine-N3)copper(II), a one-dimensional alternating copper(II). oxygen array

Use of Achiral and Meso Ligands To Convey Asymmetry in Enantioselective Catalysis

Cu(I) Complexes of 3,3‘-Polymethylene Bridged Derivatives of 2,2‘-Bi-1,10-Phenanthroline

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