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Noncovalent bonding: Stacking interactions of chelate rings of transition metal complexes

Authorized Users Only
2017
Authors
Malenov, Dusan P.
Janjić, Goran
Medaković, Vesna
Hall, Michael B.
Zarić, Snežana D.
Article (Published version)
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Abstract
Analysis of crystal structure data deposited in the Cambridge Structural Database (CSD) has shown that aromatic rings tend to stack with square planar transition metal complexes when they contain chelate rings. In these interactions, the orientation between chelate and aryl ring is a parallel-displaced orientation, like stacking interactions between aromatic molecules. In fused systems containing chelate and aryl rings, the aryl rings prefer to stack with the chelate rather than with other aryl rings. Quantum chemical calculations show that chelate-aryl stacking is stronger than aryl-aryl stacking. Interaction energies of six-membered chelates of the acetylacetonato type with benzene exceed -6 kcal/mol (CCSD(T)/CBS), more that twice as strong as that for two benzene molecules. Further analysis of the CSD has shown that chelate rings, both isolated and fused stack with other chelate rings. These chelate-chelate stacking interactions can have both face-to-face and parallel-displaced geom...etries, unlike the stacking interactions between aromatic molecules, for which face-to-face geometry is not typical. Chelate-chelate stacking is stronger than aryl-aryl stacking and stronger even than chelate-aryl stacking. Stacking energies between six-membered chelates of acetylacetonato type exceed -9 kcal/mol, while those between five-membered dithiolene chelates are even stronger. Calculated interaction energies and analysis of supramolecular structures have shown that chelate-chelate and chelate-aryl stacking must be considered in understanding the packing and organization of supramolecular systems and crystal engineering.

Keywords:
Metal chelates / Stacking interactions / Chelate aryl interactions
Source:
Coordination Chemistry Reviews, 2017, 345, 318-341
Publisher:
  • Elsevier Science Sa, Lausanne
Projects:
  • Noncovalent interactions of pi-systems and their role in molecular recognition (RS-172065)
  • NPRP grant from the Qatar National Research Fund (a member of the Qatar Foundation) [NPRP8-425-1-087]
Note:
  • Corrigendum: http://cer.ihtm.bg.ac.rs/handle/123456789/2402
  • Corrigendum: https://doi.org/10.1016/j.ccr.2018.06.009

DOI: 10.1016/j.ccr.2016.12.020

ISSN: 0010-8545

WoS: 000402873300017

Scopus: 2-s2.0-85008516893
[ Google Scholar ]
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URI
http://cer.ihtm.bg.ac.rs/handle/123456789/2234
Collections
  • Radovi istraživača / Researchers' publications
Institution
IHTM
TY  - JOUR
AU  - Malenov, Dusan P.
AU  - Janjić, Goran
AU  - Medaković, Vesna
AU  - Hall, Michael B.
AU  - Zarić, Snežana D.
PY  - 2017
UR  - http://cer.ihtm.bg.ac.rs/handle/123456789/2234
AB  - Analysis of crystal structure data deposited in the Cambridge Structural Database (CSD) has shown that aromatic rings tend to stack with square planar transition metal complexes when they contain chelate rings. In these interactions, the orientation between chelate and aryl ring is a parallel-displaced orientation, like stacking interactions between aromatic molecules. In fused systems containing chelate and aryl rings, the aryl rings prefer to stack with the chelate rather than with other aryl rings. Quantum chemical calculations show that chelate-aryl stacking is stronger than aryl-aryl stacking. Interaction energies of six-membered chelates of the acetylacetonato type with benzene exceed -6 kcal/mol (CCSD(T)/CBS), more that twice as strong as that for two benzene molecules. Further analysis of the CSD has shown that chelate rings, both isolated and fused stack with other chelate rings. These chelate-chelate stacking interactions can have both face-to-face and parallel-displaced geometries, unlike the stacking interactions between aromatic molecules, for which face-to-face geometry is not typical. Chelate-chelate stacking is stronger than aryl-aryl stacking and stronger even than chelate-aryl stacking. Stacking energies between six-membered chelates of acetylacetonato type exceed -9 kcal/mol, while those between five-membered dithiolene chelates are even stronger. Calculated interaction energies and analysis of supramolecular structures have shown that chelate-chelate and chelate-aryl stacking must be considered in understanding the packing and organization of supramolecular systems and crystal engineering.
PB  - Elsevier Science Sa, Lausanne
T2  - Coordination Chemistry Reviews
T1  - Noncovalent bonding: Stacking interactions of chelate rings of transition metal complexes
VL  - 345
SP  - 318
EP  - 341
DO  - 10.1016/j.ccr.2016.12.020
ER  - 
@article{
author = "Malenov, Dusan P. and Janjić, Goran and Medaković, Vesna and Hall, Michael B. and Zarić, Snežana D.",
year = "2017",
url = "http://cer.ihtm.bg.ac.rs/handle/123456789/2234",
abstract = "Analysis of crystal structure data deposited in the Cambridge Structural Database (CSD) has shown that aromatic rings tend to stack with square planar transition metal complexes when they contain chelate rings. In these interactions, the orientation between chelate and aryl ring is a parallel-displaced orientation, like stacking interactions between aromatic molecules. In fused systems containing chelate and aryl rings, the aryl rings prefer to stack with the chelate rather than with other aryl rings. Quantum chemical calculations show that chelate-aryl stacking is stronger than aryl-aryl stacking. Interaction energies of six-membered chelates of the acetylacetonato type with benzene exceed -6 kcal/mol (CCSD(T)/CBS), more that twice as strong as that for two benzene molecules. Further analysis of the CSD has shown that chelate rings, both isolated and fused stack with other chelate rings. These chelate-chelate stacking interactions can have both face-to-face and parallel-displaced geometries, unlike the stacking interactions between aromatic molecules, for which face-to-face geometry is not typical. Chelate-chelate stacking is stronger than aryl-aryl stacking and stronger even than chelate-aryl stacking. Stacking energies between six-membered chelates of acetylacetonato type exceed -9 kcal/mol, while those between five-membered dithiolene chelates are even stronger. Calculated interaction energies and analysis of supramolecular structures have shown that chelate-chelate and chelate-aryl stacking must be considered in understanding the packing and organization of supramolecular systems and crystal engineering.",
publisher = "Elsevier Science Sa, Lausanne",
journal = "Coordination Chemistry Reviews",
title = "Noncovalent bonding: Stacking interactions of chelate rings of transition metal complexes",
volume = "345",
pages = "318-341",
doi = "10.1016/j.ccr.2016.12.020"
}
Malenov DP, Janjić G, Medaković V, Hall MB, Zarić SD. Noncovalent bonding: Stacking interactions of chelate rings of transition metal complexes. Coordination Chemistry Reviews. 2017;345:318-341
Malenov, D. P., Janjić, G., Medaković, V., Hall, M. B.,& Zarić, S. D. (2017). Noncovalent bonding: Stacking interactions of chelate rings of transition metal complexes.
Coordination Chemistry ReviewsElsevier Science Sa, Lausanne., 345, 318-341.
https://doi.org/10.1016/j.ccr.2016.12.020
Malenov Dusan P., Janjić Goran, Medaković Vesna, Hall Michael B., Zarić Snežana D., "Noncovalent bonding: Stacking interactions of chelate rings of transition metal complexes" 345 (2017):318-341,
https://doi.org/10.1016/j.ccr.2016.12.020 .

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