Stacking interactions of metal-chelate and hydrogen-bridged rings
Конференцијски прилог (Објављена верзија)
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Stacking interactions are ubiquitous in many chemical and biological systems, and they are
of great interest in the areas of crystal engineering and materials science. Stacking interactions are
typically referred to as the interactions of aromatic molecules. However, there are moieties that
frequently form stacking interactions that are stronger than stacking interactions of aromatic
molecules. Two examples are metal-chelate rings [1] and hydrogen-bridged rings [2].
The searching of the Cambridge Structural Database (CSD) showed that metal-chelate rings
can form both chelate-aryl and chelate-chelate stacking interactions [1]. The analysis of crystal
structures also showed that C6 aromatic rings prefer stacking with chelate ring than with other C6
aromatic rings. Quantum chemical calculations explained this preference by showing that chelatearyl stacking interactions (-6.39 kcal/mol) are stronger than stacking interactions between benzene
molecules (-2.73 kcal/mol). Chelate-che...late stacking interactions are even stronger (-9.70
kcal/mol). It was shown that the nature of both chelate-benzene and chelate-chelate stacking
depends on the metal [1,3].
The analysis of the CSD crystal structures showed that planar five-membered hydrogenbridged rings frequently form stacking interactions, both with other hydrogen-bridged rings [2] and
with C6 aromatic rings [4]. Quantum chemical calculations showed that stacking interactions
between hydrogen-bridged rings can be as strong as -4.89 kcal/mol, while stacking between
benzene and hydrogen-bridged ring can be as strong as -4.38 kcal/mol.
Извор:
Molecular Modeling in Chemistry and Biochemistry, Babes-Bolyai University, Cluj-Napoca, Romania, 2018, 2018Финансирање / пројекти:
- Нековалентне интеракције pi-система и њихова улога у молекулском препознавању (RS-MESTD-Basic Research (BR or ON)-172065)
Колекције
Институција/група
Inovacioni centar / Innovation CentreTY - CONF AU - Malenov, Dušan P. AU - Blagojević Filipović, Jelena P. AU - Hall, Michael B. AU - Zarić, Snežana D. PY - 2018 UR - http://cherry.chem.bg.ac.rs/handle/123456789/5265 AB - Stacking interactions are ubiquitous in many chemical and biological systems, and they are of great interest in the areas of crystal engineering and materials science. Stacking interactions are typically referred to as the interactions of aromatic molecules. However, there are moieties that frequently form stacking interactions that are stronger than stacking interactions of aromatic molecules. Two examples are metal-chelate rings [1] and hydrogen-bridged rings [2]. The searching of the Cambridge Structural Database (CSD) showed that metal-chelate rings can form both chelate-aryl and chelate-chelate stacking interactions [1]. The analysis of crystal structures also showed that C6 aromatic rings prefer stacking with chelate ring than with other C6 aromatic rings. Quantum chemical calculations explained this preference by showing that chelatearyl stacking interactions (-6.39 kcal/mol) are stronger than stacking interactions between benzene molecules (-2.73 kcal/mol). Chelate-chelate stacking interactions are even stronger (-9.70 kcal/mol). It was shown that the nature of both chelate-benzene and chelate-chelate stacking depends on the metal [1,3]. The analysis of the CSD crystal structures showed that planar five-membered hydrogenbridged rings frequently form stacking interactions, both with other hydrogen-bridged rings [2] and with C6 aromatic rings [4]. Quantum chemical calculations showed that stacking interactions between hydrogen-bridged rings can be as strong as -4.89 kcal/mol, while stacking between benzene and hydrogen-bridged ring can be as strong as -4.38 kcal/mol. C3 - Molecular Modeling in Chemistry and Biochemistry, Babes-Bolyai University, Cluj-Napoca, Romania, 2018 T1 - Stacking interactions of metal-chelate and hydrogen-bridged rings UR - https://hdl.handle.net/21.15107/rcub_cherry_5265 ER -
@conference{ author = "Malenov, Dušan P. and Blagojević Filipović, Jelena P. and Hall, Michael B. and Zarić, Snežana D.", year = "2018", abstract = "Stacking interactions are ubiquitous in many chemical and biological systems, and they are of great interest in the areas of crystal engineering and materials science. Stacking interactions are typically referred to as the interactions of aromatic molecules. However, there are moieties that frequently form stacking interactions that are stronger than stacking interactions of aromatic molecules. Two examples are metal-chelate rings [1] and hydrogen-bridged rings [2]. The searching of the Cambridge Structural Database (CSD) showed that metal-chelate rings can form both chelate-aryl and chelate-chelate stacking interactions [1]. The analysis of crystal structures also showed that C6 aromatic rings prefer stacking with chelate ring than with other C6 aromatic rings. Quantum chemical calculations explained this preference by showing that chelatearyl stacking interactions (-6.39 kcal/mol) are stronger than stacking interactions between benzene molecules (-2.73 kcal/mol). Chelate-chelate stacking interactions are even stronger (-9.70 kcal/mol). It was shown that the nature of both chelate-benzene and chelate-chelate stacking depends on the metal [1,3]. The analysis of the CSD crystal structures showed that planar five-membered hydrogenbridged rings frequently form stacking interactions, both with other hydrogen-bridged rings [2] and with C6 aromatic rings [4]. Quantum chemical calculations showed that stacking interactions between hydrogen-bridged rings can be as strong as -4.89 kcal/mol, while stacking between benzene and hydrogen-bridged ring can be as strong as -4.38 kcal/mol.", journal = "Molecular Modeling in Chemistry and Biochemistry, Babes-Bolyai University, Cluj-Napoca, Romania, 2018", title = "Stacking interactions of metal-chelate and hydrogen-bridged rings", url = "https://hdl.handle.net/21.15107/rcub_cherry_5265" }
Malenov, D. P., Blagojević Filipović, J. P., Hall, M. B.,& Zarić, S. D.. (2018). Stacking interactions of metal-chelate and hydrogen-bridged rings. in Molecular Modeling in Chemistry and Biochemistry, Babes-Bolyai University, Cluj-Napoca, Romania, 2018. https://hdl.handle.net/21.15107/rcub_cherry_5265
Malenov DP, Blagojević Filipović JP, Hall MB, Zarić SD. Stacking interactions of metal-chelate and hydrogen-bridged rings. in Molecular Modeling in Chemistry and Biochemistry, Babes-Bolyai University, Cluj-Napoca, Romania, 2018. 2018;. https://hdl.handle.net/21.15107/rcub_cherry_5265 .
Malenov, Dušan P., Blagojević Filipović, Jelena P., Hall, Michael B., Zarić, Snežana D., "Stacking interactions of metal-chelate and hydrogen-bridged rings" in Molecular Modeling in Chemistry and Biochemistry, Babes-Bolyai University, Cluj-Napoca, Romania, 2018 (2018), https://hdl.handle.net/21.15107/rcub_cherry_5265 .