Chiral quadridentate ligands based on amino acids: template syntheses and properties of the free ligands and their transition-metal complexes

Balla, József; Bernhardt, Paul V.; Buglyó, Péter; Comba, Peter; Hambley, Trevor W.; Schmidlin, Reto; Stebler, Sandra; Várnagy, Katalin

doi:10.1039/dt9930001143

Cited by 27 publications

(27 citation statements)

References 24 publications

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“…Potentially, cis and trans isomers may exist, and weak axial co-ordination of the nitro group during cyclisation has been proposed as responsible for directing the stereochemistry dominantly to the anti isomer in the case of reactions around copper(), 24 and is supported by molecular mechanics calculations. 31 The greater tendency towards square-planar character generally found for gold(), where axial interactions are not anticipated, would limit this behaviour.…”

Section: Resultsmentioning

confidence: 99%

Gold(III) template synthesis of a pendant-arm macrocycle

Rossignoli¹,

Bernhardt²,

Lawrance³

et al. 1997

J. Chem. Soc., Dalton Trans.

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Section: Resultsmentioning

confidence: 99%

Gold(III) template synthesis of a pendant-arm macrocycle

Rossignoli¹,

Bernhardt²,

Lawrance³

et al. 1997

J. Chem. Soc., Dalton Trans.

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“…Yield: 4.18 g (57%). 1 The solids NTA (0.27 g, 1.41 mmol), and DCC (1.05 g, 5.10 mmol. 3.6 equiv) were placed in a flask equipped with a magnetic stirrer bar under nitrogen.…”

Section: Methodsmentioning

confidence: 99%

“…[1][2][3][4] Free amino acids and derivatives thereof have also been used extensively as ligands and chiral auxiliaries in a variety of asymmetric syntheses; this field has been reviewed. [5][6][7] For example, chiral amino acids have been incorporated into phosphine and phosphite ligands for asymmetric catalysis.…”

mentioning

confidence: 99%

Synthesis of Dianionic and Trianionic Chiral, Chelating Ligands Based on Amino Acids

et al. 2008

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Abstract:The synthesis of two new families of amino acid-containing chiral ligands, based on methyliminodiacetic acid and nitrilotriacetic acid cores, has been accomplished using a simple protection, solution phase amide coupling and deprotection strategy. The amino acids glycine, leucine, aspartic acid and phenylalanine were used to demonstrate the versatility of the synthetic route, and that no epimerisation occurs. Thus, the tridentate ligands bear C 3 symmetry, while the bidentate ligands have C 1 symmetry.

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“…b-Amino acids are known as intermediates in different biological transformations involving oligometals [1,2]. However, not many results have been reported which refer to the complexes containing these acids as ligands.…”

Section: Introductionmentioning

confidence: 99%

Protonation behaviour of N,N′-piperazine-dipropionic acid

Mateescu

Wikete²,

Costişor

et al. 2005

Comptes Rendus. Chimie

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The overall protonation constants of N,N′-piperazine-dipropionic acid (PDPA) were calculated with SUPERQUAD and PSE-QUAD computer programs, at 25 and 37°C and an ionic strength of 0.1 mol dm -3 (KCl). There is a good agreement between the values calculated with the two programs. The obtained values were checked by a simulation titration curve and by the protonation (observed and calculated) curves for C L = 2.0716 mmol dm -3 at 25°C. A two-step deprotonation mechanism is proposed. In the first step the deprotonation occurs to the carboxyl group and in the second step it is the nitrogen atom of the piperazine ring which undergoes deprotonation. To cite this article: C.

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Chiral quadridentate ligands based on amino acids: template syntheses and properties of the free ligands and their transition-metal complexes

Cited by 27 publications

References 24 publications

Gold(III) template synthesis of a pendant-arm macrocycle

Gold(III) template synthesis of a pendant-arm macrocycle

Synthesis of Dianionic and Trianionic Chiral, Chelating Ligands Based on Amino Acids

Protonation behaviour of N,N′-piperazine-dipropionic acid

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