Coordination compounds of chelating ligands containing imidazole groups. Synthesis and characterization of copper(I) and copper(II) complexes of N,N,N',N'-tetrakis[(2-benzimidazolyl)methyl]-1,2-ethanediamine and the x-ray structure of an [N,N,N',N'-tetrakis[(2-benzimidazolyl)methyl]-1,2-ethanediamine]copper(II) cation

Birker, P. J. M. W. L.; Hendriks, H. M. J.; Reedijk, J.; Verschoor, G. C.

doi:10.1021/ic50222a010

Cited by 38 publications

(8 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This coordination mode is rare in copper(II) complexes with tri- and polydentate amine ligands. A comparable situation was described by Reedijk et al for a sterically hindered copper complex of the hexadentate EDTB (EDTB = N , N , N ‘, N ‘-tetrakis[(2-benzimidazolyl)methyl]-1,2-ethanediamine) 6 Ball and stick plot of the calculated structure of [(Ac-bpa)CuCl 2 ].…”

Section: Calculated Structuressupporting

confidence: 70%

The Activation of Tertiary Carboxamides in Metal Complexes: An Experimental and Theoretical Study on the Methanolysis of Acylated Bispicolylamine Copper(II) Complexes

et al. 2004

View full text Add to dashboard Cite

It is a well-established concept that the C-N bond cleavage of carboxamide functions is facilitated by the coordination of a metal ion to the carbonyl oxygen atom. In contrast, the alternative C-N bond activation by coordination of a neutral tertiary carboxamide nitrogen atom has not been studied. We present the first results on the effect of nitrogen pyramidalization in N-coordinated metal complexes on the methanolysis of tertiary carboxamide groups. An analysis of the reactions products obtained from the methanol cleavage of [(N-Acyl-bpa)Cu]2+ (bpa = N,N-bispicolylamine) complexes is presented together with experimental and high-level theoretically calculated structures. The strong effect of different anions on the amide pyramidalization and subsequent C-N-bond cleavage is evaluated. We show that dichloro complexes [(N-Acyl-bpa)CuCl2] have much less activated amide groups than the corresponding triflate species. They should therefore be less reactive. However, [(N-Acyl-bpa)CuCl2] complexes dissociate in solution to give cationic monochloro complexes [(N-Acyl-bpa)Cu(S)Cl]+ (S = solvent molecule). Theoretical calculations show that the amide pyramidalization in the monochloro complexes is equal to that in the corresponding CF3SO3- salts. Consequently, chloro and triflato complexes are cleaved with similar rates and efficiencies. Parallels to and differences in the reactivity of purely organic distorted amides are discussed.

show abstract

Section: Calculated Structuressupporting

confidence: 70%

The Activation of Tertiary Carboxamides in Metal Complexes: An Experimental and Theoretical Study on the Methanolysis of Acylated Bispicolylamine Copper(II) Complexes

et al. 2004

View full text Add to dashboard Cite

show abstract

“…Ligand Synthesis. Tris-benzimidazole ligand (BimH) 3 and analogues H(BimH) 2 and (BimH) 2 C 2 (BimH) 2 were obtained by condensation of 1,2-phenylenediamine with the corresponding tri-, di-, and tetracarboxylic acid in boiling ethylene glycol. A similar condensation reaction between 1,2-aminothiophenol and nitrilotriacetonitrile or iminodiacetonitrile was used to synthesize benzothiazole ligands (Bth) 3 and (H)(Bth) 2 .…”

Section: Methodsmentioning

confidence: 99%

Benzimidazole and Related Ligands for Cu-Catalyzed Azide−Alkyne Cycloaddition

et al. 2007

View full text Add to dashboard Cite

Tris(2-benzimidazolylmethyl)amines have been found to be superior accelerating ligands for the copper(I)-catalyzed azide-alkyne cycloaddition reaction. Candidates bearing different benzimidazole N-substituents as well as benzothiazole and pyridyl ligand arms were evaluated by absolute rate measurements under relatively dilute conditions by aliquot quenching kinetics and by relative rate measurements under concentrated conditions by reaction calorimetry. Benzimidazole-based ligands with pendant alkylcarboxylate arms proved to be advantageous in the latter case. The catalyst system was shown to involve more than one active species, providing a complex response to changes in pH and buffer salts and the persistence of high catalytic rate in the presence of high concentrations of coordinating ligands. The water-soluble ligand (BimC4A)3 was found to be especially convenient for the rapid and high-yielding synthesis of several functionalized triazoles with 0.01-0.5 mol % Cu.

show abstract

“…Previous studies showed that DNA microarrays can be prepared easily and cost-effectively by combining μCP with copper-free click chemistry to immobilize DNA strands on glass substrates . In the current work, a SPAAC protocol ,− was adopted for the immobilization of PA ( 1 ) ink onto an azide substrate, as it dispels the need for copper(I) catalysis as required in conventional copper-catalyzed Huisgen [3 + 2] azide–alkyne cycloaddition (CuAAC). , We avoided utilizing CuAAC chemistry because PAs incorporate imidazole units, which have known affinity for copper ions . The core sequence of PA ( 1 ) was chosen as a paradigm for this study by virtue of its high binding affinity for the target DNA sequence 5′-WWGGWCW-3′ (where W = A/T) .…”

Section: Resultsmentioning

confidence: 99%

Sequence-Selective Detection of Double-Stranded DNA Sequences Using Pyrrole–Imidazole Polyamide Microarrays

et al. 2013

View full text Add to dashboard Cite

We describe a microarray format that can detect double-stranded DNA sequences with a high degree of sequence selectivity. Cyclooctyne-derivatized pyrrole-imidazole polyamides were immobilized on azide-modified glass substrates using microcontact printing and a strain-promoted azide-alkyne cycloaddition (SPAAC) reaction. These polyamide-immobilized substrates selectively detected a seven-base-pair binding site incorporated within a double-stranded oligodeoxyribonucleotide sequence even in the presence of an excess of a sequence with a single-base-pair mismatch.

show abstract

Abstract: Durch Reaktion des Liganden mit entsprechenden Cu‐Salzen werden die Komplexe (I)‐(III) erhalten (keine Ausb.‐Angaben), die elektronenabsorptions‐ und ESR‐spektroskopisch charakterisiert werden.

Cited by 38 publications

References 1 publication

The Activation of Tertiary Carboxamides in Metal Complexes: An Experimental and Theoretical Study on the Methanolysis of Acylated Bispicolylamine Copper(II) Complexes

The Activation of Tertiary Carboxamides in Metal Complexes: An Experimental and Theoretical Study on the Methanolysis of Acylated Bispicolylamine Copper(II) Complexes

Benzimidazole and Related Ligands for Cu-Catalyzed Azide−Alkyne Cycloaddition

Sequence-Selective Detection of Double-Stranded DNA Sequences Using Pyrrole–Imidazole Polyamide Microarrays

Contact Info

Product

Resources

About