C–H⋯π interactions in the metal–porphyrin complexes with chelate ring as the H acceptor

Medaković, Vesna B.; Milčić, Miloš K.; Bogdanović, Goran A.; Zarić, Snežana D.

doi:10.1016/j.jinorgbio.2004.08.012

Cited by 58 publications

(30 citation statements)

References 45 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In our previous work we showed that porphyrin -system in metal complexes and in proteins could be involved in CH/ interactions [22,23]. Searching structures of porphyrincontaining proteins from the Protein Data Bank it was revealed that -system of every porphyrin ring is involved in CH/ interactions and most of the porphyrins are making several interactions.…”

Section: Introductionmentioning

confidence: 99%

Hydrogen Bonds and Hydrophobic Interactions of Porphyrins in Porphyrin-Containing Proteins

Stojanovic¹,

Zarić²

2009

TOSBJ

View full text Add to dashboard Cite

Structures of porphyrin-containing proteins from the Protein Data Bank (PDB) Select January 2007, were searched in order to find and systematically characterize hydrogen bonds and hydrophobic interactions of porphyrins in proteins. The results revealed that every porphyrin is involved in at least one hydrogen bond, most of the porphyrins form several, while some of them form up to thirteen hydrogen bonds. In most of the hydrogen bonds propionate groups of porphyrins interact with side-chains of residues. The most frequently observed donor is side chain of arginine. Histidine, lysine, threonine, serine and tyrozine form substantial number of hydrogen bonds too. The study has revealed that hydrophobic interactions are common between porphyrin and protein. Side-chains hydrophobic interactions are more frequent than those with backbone. The average conservation score for the amino acids making hydrogen bonds (7.2) and hydrophobic interactions (7.3) is statistically significantly higher than for the amino acids that are not involved in noncovalent interactions (5.7) with the porphyrin, indicating importance of hydrogen bonds and hydrophobic interactions with the porphyrin.

show abstract

Section: Introductionmentioning

confidence: 99%

Hydrogen Bonds and Hydrophobic Interactions of Porphyrins in Porphyrin-Containing Proteins

Stojanovic¹,

Zarić²

2009

TOSBJ

View full text Add to dashboard Cite

show abstract

“…These chelate ring π -systems can potentially be involved in CH-π interactions. Such interactions have been identified in the crystal structures of transition-metal complexes [21,22] and in structures of porphyrin-containing proteins [23]. A summary is presented below.…”

Section: Ch π Interactions In Metal-porphyrin Complexesmentioning

confidence: 93%

“…. .π and stacking interactions of chelate rings [8,[18][19][20][21][22][23][24][25][26][27][28]. Other groups have reported CH.…”

Section: Interactions With π -Systems Of Chelate Ringsmentioning

confidence: 99%

Noncovalent Interactions of π‐Systems in Crystal Structures of Transition‐Metal Complexes

Janjić

Zarić

2012

The Importance of Pi‐Interactions in Crystal Engineering

Self Cite

View full text Add to dashboard Cite

In the last decade several noncovalent interactions involving π -systems that are quite specific to the crystal structures of transition-metal complexes or organometallic compounds have been unveiled. These noncovalent interactions can involve two types of π -systems. The first type comprises π -systems of organic molecules, often aromatic, whereas the second type comprises planar chelate rings with delocalised π -bonds.The first type of π -systems, organic molecules, interact with ligands coordinated to a metal. The interactions can be classified as metal-ligand aromatic cation-π interactions (MLACπ ) and metal-ligand XH. . .π (MLXH. . .π) interactions. In MLACπ interactions, a cationic transition-metal complex interacts with a π -system. Depending on the charge of the complex, interactions can be very strong, up to 30 kcal/mol. In all described cases of MLACπ interactions, the hydrogen atoms of the ligand are oriented towards the π -system. Accordingly, these interactions can be considered also as charge-assisted XH. . .π interactions.

show abstract

“…Recently, a few studies of noncovalent interactions with the π-system of chelate rings were published [18,[23][24][25][26][27][28][29][30][31]. The delocalized π-system of the chelate rings can be considered as a soft base, similar to double and triple bonds or aromatic rings, and could be connected with an assumption that planar chelate rings with delocalized π-bonds can have aromatic character [31].…”

Section: Introductionmentioning

confidence: 99%

“…The delocalized π-system of the chelate rings can be considered as a soft base, similar to double and triple bonds or aromatic rings, and could be connected with an assumption that planar chelate rings with delocalized π-bonds can have aromatic character [31]. The chelate ring can be involved in CH/π interactions with organic moieties and in stacking interactions with phenyl rings [18,[23][24][25][26][27][28][29][30].…”

Section: Introductionmentioning

confidence: 99%

Influence of metal and ligand types on stacking interactions of phenyl rings with square-planar transition metal complexes

Sredojević

Tomić²,

Zarić

2007

Open Chemistry

View full text Add to dashboard Cite

Abstract:In order to find out whether metal type influences the stacking interactions of phenyl rings in square-planar complexes, geometrical parameters for Cu, Ni, Pd and Pt complexes, with and without chelate rings, were analyzed and compared. By searching the Cambridge Structural Database, 220 structures with Cu complexes, 211 with Ni complexes, 285 with Pd complexes, and 220 with Pt complexes were found. The results show that the chelate ring has a tendency to make the stacking interaction with the phenyl ring independent of metal type in the chelate ring. However, there are some differences among metals for complexes without a chelate ring. There are a number of structures containing Pd and Pt complexes, without chelate rings, that have short carbon-metal distances and parallel orientations of the phenyl ring with respect to the coordination plane. It was found that some of these complexes have a common fragment, CN, as a part of the ligands. This indicates that the CN supports stacking interactions of square planar complexes with the phenyl ring.

show abstract

C–H⋯π interactions in the metal–porphyrin complexes with chelate ring as the H acceptor

Cited by 58 publications

References 45 publications

Hydrogen Bonds and Hydrophobic Interactions of Porphyrins in Porphyrin-Containing Proteins

Hydrogen Bonds and Hydrophobic Interactions of Porphyrins in Porphyrin-Containing Proteins

Noncovalent Interactions of π‐Systems in Crystal Structures of Transition‐Metal Complexes

Influence of metal and ligand types on stacking interactions of phenyl rings with square-planar transition metal complexes

Contact Info

Product

Resources

About