Stacking vs. CH–π interactions between chelate and aryl rings in crystal structures of square-planar transition metal complexes

Sredojević, Dušan N.; Bogdanović, Goran A.; Tomić, Zoran D.; Zarić, Snežana D.

doi:10.1039/b704302c

Cited by 64 publications

(37 citation statements)

References 70 publications

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“…The data in Figure 3 show that most of the parallel contacts have the normal distances between 3.0 and 3.5 Å. These are distances typical for stacking of organic aromatic rings (3-4 Å) [17][18][19][20][21][22] and other planar rings that form stacking interactions [24][25][26][27][43][44][45][46]. The data in Figure 3 show that most of the parallel contacts have the normal distances between 3.0 and 3.5 Å.…”

Section: Search and Analysis Of Crystal Structures From The Csdmentioning

confidence: 86%

“…Interestingly, several studies showed that stacking interactions of other planar molecules can be even stronger than stacking between aromatic molecules , indicating the importance of these interactions. Analysis of the crystal structures from Cambridge Structural Database (CSD) have shown that planar chelate rings with delocalized π-bonds can form stackinginteractions with C 6 -aromatic rings, and with other chelate rings [24][25][26][27]. The interaction energies of nickel and copper six-membered chelate rings with benzene, calculated at very acurate CCSD(T)/CBS level, are´4.77 and´6.39 kcal/mol respectively [43,44], remarkably stronger than stacking interaction between two benzene molecules,´2.73 kcal/mol [10].…”

Section: Introductionmentioning

confidence: 99%

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Very Strong Parallel Interactions Between Two Saturated Acyclic Groups Closed with Intramolecular Hydrogen Bonds Forming Hydrogen-Bridged Rings

2016

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Saturated acyclic four-atom groups closed with a classic intramolecular hydrogen bond, generating planar five-membered rings (hydrogen-bridged quasi-rings), in which at least one of the ring atoms is bonded to other non-ring atoms that are not in the ring plane and, thus, capable to form intermolecular interactions, were studied in this work, in order to find the preferred mutual positions of these species in crystals and evaluate strength of intermolecular interactions. We studied parallel interactions of these rings by analysing crystal structures in the Cambridge Structural Database (CSD) and by quantum chemical calculations. The rings can have one hydrogen atom out of the ring plane that can form hydrogen bonds between two parallel rings. Hence, in these systems with parallel rings, two types of hydrogen bonds can be present, one in the ring, and the other one between two parallel rings. The CSD search showed that 27% of the rings in the crystal structures form parallel interactions. The calculations at very accurate CCSD(T)/CBS level revealed strong interactions, in model systems of thiosemicarbazide, semicarbazide and glycolamide dimers the energies are´9.68,´7.12 and 4.25 kcal/mol. The hydrogen bonds between rings, as well as dispersion interactions contribute to the strong interaction energies.

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Section: Search and Analysis Of Crystal Structures From The Csdmentioning

confidence: 86%

Section: Introductionmentioning

confidence: 99%

Very Strong Parallel Interactions Between Two Saturated Acyclic Groups Closed with Intramolecular Hydrogen Bonds Forming Hydrogen-Bridged Rings

2016

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“…. .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%

“…. .π interactions [27]. The crystal structures of square-planar transition-metal complexes deposited in the CSD with close contacts between planar chelate rings and C 6 -aryl rings were analysed.…”

Section: Comparison Of Stacking and Ch π Interactions Betweenmentioning

confidence: 99%

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

Janjić

Zarić

2012

The Importance of Pi‐Interactions in Crystal Engineering

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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.

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Crystal Engineering

Tiekink

2012

Supramolecular Chemistry

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Crystal engineering is an emerging discipline whereby practitioners aim to arrange molecules, both organic and metalorganic, in the crystalline phase by rational design. This challenge requires the exploitation of well‐known supramolecular glues such as hydrogen bonding and coordinate bonding. These are augmented by a myriad of nominally weaker and less directional noncovalent interactions that, increasingly, are being demonstrated as important in crystal structure design. Applications in fields as diverse as pharmaceuticals, photoluminescent materials, and metalorganic frameworks for gas storage are some of the motivations for crystal engineering that draw together scientists from a wide range of disciplines. This illustrated overview summarizes factors that dictate the ways molecules aggregate in the solid state, including a description of the diverse types of noncovalent interactions and other crystal packing principles that have being identified as being important in stabilizing crystal structure. Applications of crystal engineering drawn from both the organic and metalorganic realms are discussed. These include cocrystal formation, solid‐state reactions, and metalorganic framework structures. Furthermore, the importance of in silico studies and data mining as they relate to crystal engineering is highlighted throughout.

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Stacking vs. CH–π interactions between chelate and aryl rings in crystal structures of square-planar transition metal complexes

Cited by 64 publications

References 70 publications

Very Strong Parallel Interactions Between Two Saturated Acyclic Groups Closed with Intramolecular Hydrogen Bonds Forming Hydrogen-Bridged Rings

Very Strong Parallel Interactions Between Two Saturated Acyclic Groups Closed with Intramolecular Hydrogen Bonds Forming Hydrogen-Bridged Rings

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

Crystal Engineering

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