Structures and stabilities of metal(II) (Co(II), Ni(II), Cu(II), Zn(II), Pd(II), Cd(II)) compounds of N-protected amino acids

Corradi, A. Bonamartini

doi:10.1016/0010-8545(92)80020-r

Cited by 35 publications

(4 citation statements)

References 124 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The value of the latter angle suggests that the lone pair is stereochemically active in the direction opposite to that of the Pb−O5 bond. Bond distances and angles within the ligand and the bpy molecule fall in the range of literature data . Crystal packing is mainly due to interchain ring stacking interactions (in the range 3.39−3.88 Å) involving bpy molecules.…”

Section: Resultsmentioning

confidence: 81%

“…Compound 1 is the first example of a structurally characterized Pb 2+ N,O-chelate complex. The Pb−N bond (2.38(1) Å) is 0.4 Å longer than the average Cu−N bond in analogous complexes of the five-coordinate Cu 2+ ion it turns out that the deprotonated amide nitrogen has a stronger affinity for dipositive lead than for the copper ion, consistent with the greater step constant for the formation of the nitrogen-deprotonated species from the precursor carboxylate complex.…”

Section: Discussionmentioning

confidence: 81%

“…The five atoms of the glycine-like ring are almost planar, with deviations from the mean plane from −0.077 to 0.156 Å. Bond distances and angles within the ligand fall in the typical range for metal complexes of tsgly dianions …”

Section: Resultsmentioning

confidence: 90%

“…Crystal packing is mainly due to O···O contacts involving a lattice water molecule. Bond distances and angles within the ligand fall in the range of literature data …”

Section: Resultsmentioning

confidence: 91%

See 3 more Smart Citations

Amide Group Coordination to the Pb²⁺ Ion

et al. 1996

View full text Add to dashboard Cite

The binary and ternary (2,2'-bipyridine) complexes of dipositive lead formed by N-carbonyl and N-sulfonyl amino acids, which are ligands containing the peptide and the sulfonamide group, respectively, were investigated in aqueous solution by NMR and differential pulse polarography, and some were also characterized crystallographically. N-Tosylglycine, N-tosyl-beta-alanine, and N-benzoylglycine behave as simple carboxylate ligands at acid pH, while around neutrality they switch to dianionic N,O-bidentate chelating ligands due to the involvement of the deprotonated amide nitrogen as an additional donor site. The same coordination behavior is maintained in the presence of 2,2'-bipyridine. The binary and ternary species formed in solution, and their stability constants were determined and compared with those of the homologous complexes of Pd(2+), Cu(2+), Cd(2+), and Zn(2+). The Pb(2+) ion is the only dipositive metal which is effective in promoting peptide nitrogen deprotonation in benzoylglycine. The molecular structures of [Pb(N-tosylglycinato-N,O)(H(2)O)] (1), [Pb(N-benzoylglycinato-O)(2)(H(2)O)(2)].2H(2)O (2), and [Pb(N-tosylglycinato-O)(2)(bpy)] (3) were determined by X-ray crystallography (O and N,O refer to the ligands binding as carboxylates and as N,O-chelating dianions, respectively). These compounds are all polymeric with six- to eight-coordinate metals showing distorted coordination geometries indicative of a stereochemically active metal lone pair. Polymerization is invariably determined by a bidentate chelate carboxylate group with one oxygen bridging between two metals, and in 2 and 3 it occurs through the formation of chains of Pb(2)O(2) square-planar rings. The binding set in 1, involving a deprotonated amide nitrogen and a sulfonic oxygen, is unprecedented for the Pb(2+) ion. This work provides new information on the solution and solid state chemistry of dipositive lead with ligands of biological interest, a research area that has received little attention in the past, although it is of great relevance for understanding the mechanisms of metal toxicity.

show abstract

Section: Resultsmentioning

confidence: 81%

Section: Discussionmentioning

confidence: 81%

Section: Resultsmentioning

confidence: 90%

“…Crystal packing is mainly due to O···O contacts involving a lattice water molecule. Bond distances and angles within the ligand fall in the range of literature data …”

Section: Resultsmentioning

confidence: 91%

See 2 more Smart Citations

Amide Group Coordination to the Pb²⁺ Ion

et al. 1996

View full text Add to dashboard Cite

show abstract

Syntheses, Crystal Structures and Properties of Lanthanide(III) Complexes with N‐Protected Aminoacid of N‐p‐Tosylglycinate

Zhang

Chen

et al. 2006

Chin. J. Chem.

View full text Add to dashboard Cite

Complexes {[Ln(H 2 O) 2 (TsGlyH) 3 ] m •nH 2 O} ∞ (Ln＝La (1), m＝2, n＝6; Nd (2), m＝2, n＝7; Eu (3), m＝2, n＝ 0; Gd (4), m＝2, n＝2; Er (5), m＝3, n＝5 and Yb (6), m＝3, n＝0, TsGlyH＝N-p-tosylglycine monoanion), have been prepared and characterized by IR spectra, elemental analysis, and TG-DTG. 4 and 5 were structurally determined by X-ray diffraction analysis, showing that both of them are comprised of a one dimensional chain structure established via the coordination of µ-carboxylate groups from N-p-tosylglycinate to the corresponding lanthanide(III) ions. The one dimensional chains were found inclined to form two-dimensional network via hydrogen bonding and then three dimensional network structure via non-classical hydrogen bonding. The fluorescence spectra of them revealed that the fluorescence of the ligand was quenched by Ln(III) ions. In the tested biological activity experiments, they behaved inhibiting effects against the growth of bacteria, indicating that it is a potential medicament worthy of further investigation.

show abstract

Metallkomplexe mit biologisch wichtigen Liganden. LXXXII. Triphenylphosphan‐Molybdän‐, Wolfram‐, Ruthenium‐ und Iridium‐Komplexe mit N‐acylierten α‐Aminocarboxylaten

Severin

Koch

Polborn

et al. 1996

Zeitschrift anorg allge chemie

View full text Add to dashboard Cite

Die Hydrido‐Komplexe RuHCl(CO)(PPh3)3, RuH2(PPh3)4 und IrH3(PPh3)3 reagieren mit N‐Acyl‐α‐Amino‐carbonsäuren unter Bildung der Carboxylat‐Komplexe RuCl(O2CCHRNHCOR′)(CO)(PPh3)2 (1–3), RuH(O2CCHRNHCOR′)(PPh3)3 (4–6) und IrH2(O2CCH2NHCOPh)(PPh3)3 (7). Die Struktur von RuCl(O2CCH2NHCOPh)(CO)(PPh3)2 (1) wurde röntgenographisch bestimmt. Phosphan‐Komplexe der Formel MBr(O2CCH2NHCOR)(CO)2(PPh3)2 (M = Mo, W) (8–12) und Mo(O2CCHRNHCOR′)2(CO)2(PPh3)2 (13–17) entstehen bei der Umsetzung von MBr2(CO)2(PPh3)2 mit einem bzw. zwei Äquivalenten N‐Acyl‐α‐Aminocarboxylat‐Anionen.

show abstract

Structures and stabilities of metal(II) (Co(II), Ni(II), Cu(II), Zn(II), Pd(II), Cd(II)) compounds of N-protected amino acids

Cited by 35 publications

References 124 publications

Amide Group Coordination to the Pb²⁺ Ion

Amide Group Coordination to the Pb²⁺ Ion

Syntheses, Crystal Structures and Properties of Lanthanide(III) Complexes with N‐Protected Aminoacid of N‐p‐Tosylglycinate

Metallkomplexe mit biologisch wichtigen Liganden. LXXXII. Triphenylphosphan‐Molybdän‐, Wolfram‐, Ruthenium‐ und Iridium‐Komplexe mit N‐acylierten α‐Aminocarboxylaten

Contact Info

Product

Resources

About

Structures and stabilities of metal(II) (Co(II), Ni(II), Cu(II), Zn(II), Pd(II), Cd(II)) compounds of N-protected amino acids

Cited by 35 publications

References 124 publications

Amide Group Coordination to the Pb2+ Ion

Amide Group Coordination to the Pb2+ Ion

Syntheses, Crystal Structures and Properties of Lanthanide(III) Complexes with N‐Protected Aminoacid of N‐p‐Tosylglycinate

Metallkomplexe mit biologisch wichtigen Liganden. LXXXII. Triphenylphosphan‐Molybdän‐, Wolfram‐, Ruthenium‐ und Iridium‐Komplexe mit N‐acylierten α‐Aminocarboxylaten

Contact Info

Product

Resources

About

Amide Group Coordination to the Pb²⁺ Ion

Amide Group Coordination to the Pb²⁺ Ion