Noncovalent interactions of pi-systems and their role in molecular recognition

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Noncovalent interactions of pi-systems and their role in molecular recognition (en)
Нековалентне интеракције pi-система и њихова улога у молекулском препознавању (sr)
Nekovalentne interakcije pi-sistema i njihova uloga u molekulskom prepoznavanju (sr_RS)
Authors

Publications

Synthesis, characterization and crystal structure of Cu(II) complex with a diimine-dioxime ligand, [Cu-2(LH)(2)](ClO4)(2). Influence of the weak Cu center dot center dot center dot O(perchlorate) interaction on the structure of the Cu2N2O2 metallocycle

Mirković, Marija D.; Nikolić, Nadežda S.; Mijin, Dušan Ž.; Ivic, Milka Avramov; Kapor, Agneš; Tomić, Zoran D.

(2014)

TY  - JOUR
AU  - Mirković, Marija D.
AU  - Nikolić, Nadežda S.
AU  - Mijin, Dušan Ž.
AU  - Ivic, Milka Avramov
AU  - Kapor, Agneš
AU  - Tomić, Zoran D.
PY  - 2014
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/6018
AB  - The diimine dioxime ligand, 3,3-(1,4-butanediyl-dinitrilo)bis-2-pentanone, 2,2-dioxime (LH2), containing a N-4 donor set was prepared by the Schiff base condensation of 2-hydroxyimino-3-pentanone and 1,4-diaminobutane in two ways: in a protic and in an aprotic solvent. A higher yield of the (LH2) imine was obtained when the synthesis was performed using a protic solvent (C2H5OH) instead of aprotic benzene (78 and 30 %, respectively). The Cu(II) metal complex of diimine dioxime was synthesized in CH3OH from the perchlorate salt of LH2 in a 1:1 mole ratio. The isolated complex was characterized by the elemental analysis, IR spectroscopy and cyclic voltammetry. The structure of [Cu-2(LH)(2)](ClO4)(2) was determined by single-crystal X-ray diffraction analysis. Comparison with structurally related diimine dioxime Cu(II) complexes revealed the influence of a weak Cu center dot center dot center dot O(perchlorate) interaction on the geometry of the metallocycle.
T2  - Journal of the Serbian Chemical Society
T1  - Synthesis, characterization and crystal structure of Cu(II) complex with a diimine-dioxime ligand, [Cu-2(LH)(2)](ClO4)(2). Influence of the weak Cu center dot center dot center dot O(perchlorate) interaction on the structure of the Cu2N2O2 metallocycle
VL  - 79
IS  - 5
SP  - 545
EP  - 556
DO  - 10.2298/JSC130910120M
ER  - 
@article{
author = "Mirković, Marija D. and Nikolić, Nadežda S. and Mijin, Dušan Ž. and Ivic, Milka Avramov and Kapor, Agneš and Tomić, Zoran D.",
year = "2014",
abstract = "The diimine dioxime ligand, 3,3-(1,4-butanediyl-dinitrilo)bis-2-pentanone, 2,2-dioxime (LH2), containing a N-4 donor set was prepared by the Schiff base condensation of 2-hydroxyimino-3-pentanone and 1,4-diaminobutane in two ways: in a protic and in an aprotic solvent. A higher yield of the (LH2) imine was obtained when the synthesis was performed using a protic solvent (C2H5OH) instead of aprotic benzene (78 and 30 %, respectively). The Cu(II) metal complex of diimine dioxime was synthesized in CH3OH from the perchlorate salt of LH2 in a 1:1 mole ratio. The isolated complex was characterized by the elemental analysis, IR spectroscopy and cyclic voltammetry. The structure of [Cu-2(LH)(2)](ClO4)(2) was determined by single-crystal X-ray diffraction analysis. Comparison with structurally related diimine dioxime Cu(II) complexes revealed the influence of a weak Cu center dot center dot center dot O(perchlorate) interaction on the geometry of the metallocycle.",
journal = "Journal of the Serbian Chemical Society",
title = "Synthesis, characterization and crystal structure of Cu(II) complex with a diimine-dioxime ligand, [Cu-2(LH)(2)](ClO4)(2). Influence of the weak Cu center dot center dot center dot O(perchlorate) interaction on the structure of the Cu2N2O2 metallocycle",
volume = "79",
number = "5",
pages = "545-556",
doi = "10.2298/JSC130910120M"
}
Mirković, M. D., Nikolić, N. S., Mijin, D. Ž., Ivic, M. A., Kapor, A.,& Tomić, Z. D.. (2014). Synthesis, characterization and crystal structure of Cu(II) complex with a diimine-dioxime ligand, [Cu-2(LH)(2)](ClO4)(2). Influence of the weak Cu center dot center dot center dot O(perchlorate) interaction on the structure of the Cu2N2O2 metallocycle. in Journal of the Serbian Chemical Society, 79(5), 545-556.
https://doi.org/10.2298/JSC130910120M
Mirković MD, Nikolić NS, Mijin DŽ, Ivic MA, Kapor A, Tomić ZD. Synthesis, characterization and crystal structure of Cu(II) complex with a diimine-dioxime ligand, [Cu-2(LH)(2)](ClO4)(2). Influence of the weak Cu center dot center dot center dot O(perchlorate) interaction on the structure of the Cu2N2O2 metallocycle. in Journal of the Serbian Chemical Society. 2014;79(5):545-556.
doi:10.2298/JSC130910120M .
Mirković, Marija D., Nikolić, Nadežda S., Mijin, Dušan Ž., Ivic, Milka Avramov, Kapor, Agneš, Tomić, Zoran D., "Synthesis, characterization and crystal structure of Cu(II) complex with a diimine-dioxime ligand, [Cu-2(LH)(2)](ClO4)(2). Influence of the weak Cu center dot center dot center dot O(perchlorate) interaction on the structure of the Cu2N2O2 metallocycle" in Journal of the Serbian Chemical Society, 79, no. 5 (2014):545-556,
https://doi.org/10.2298/JSC130910120M . .
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Influence of the weak interaction on the structure of metallocycle in binuclear copper(II) complex

Tomić, Zoran D.; Mirković, Marija D.; Nikolić, Nadežda S.; Stanković, Dragana; Mijin, Dušan Ž.; Kapor, Agneš

(Society of Physical Chemists of Serbia, 2014)

TY  - CONF
AU  - Tomić, Zoran D.
AU  - Mirković, Marija D.
AU  - Nikolić, Nadežda S.
AU  - Stanković, Dragana
AU  - Mijin, Dušan Ž.
AU  - Kapor, Agneš
PY  - 2014
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/9258
AB  - The structure of binuclear Cu(II) complex containing double oximato
bridges was determined by the single-crystal X-ray diffraction analysis.
Copper is five-coordinated with perchlorato anion present at the borderline
of semi-coordination. Comparison with the structurally related diiminedioxime
Cu(II) complexes revealed the influence of the weak
Cu···O(perchlorate) interaction on the geometry of the metallocycle.
PB  - Society of Physical Chemists of Serbia
C3  - PHYSICAL CHEMISTRY 2014: 12th International Conference on Fundamental and Applied Aspects of Physical Chemistry
T1  - Influence of the weak interaction on the structure of metallocycle in binuclear copper(II) complex
VL  - M-05-P
ER  - 
@conference{
author = "Tomić, Zoran D. and Mirković, Marija D. and Nikolić, Nadežda S. and Stanković, Dragana and Mijin, Dušan Ž. and Kapor, Agneš",
year = "2014",
abstract = "The structure of binuclear Cu(II) complex containing double oximato
bridges was determined by the single-crystal X-ray diffraction analysis.
Copper is five-coordinated with perchlorato anion present at the borderline
of semi-coordination. Comparison with the structurally related diiminedioxime
Cu(II) complexes revealed the influence of the weak
Cu···O(perchlorate) interaction on the geometry of the metallocycle.",
publisher = "Society of Physical Chemists of Serbia",
journal = "PHYSICAL CHEMISTRY 2014: 12th International Conference on Fundamental and Applied Aspects of Physical Chemistry",
title = "Influence of the weak interaction on the structure of metallocycle in binuclear copper(II) complex",
volume = "M-05-P"
}
Tomić, Z. D., Mirković, M. D., Nikolić, N. S., Stanković, D., Mijin, D. Ž.,& Kapor, A.. (2014). Influence of the weak interaction on the structure of metallocycle in binuclear copper(II) complex. in PHYSICAL CHEMISTRY 2014: 12th International Conference on Fundamental and Applied Aspects of Physical Chemistry
Society of Physical Chemists of Serbia., M-05-P.
Tomić ZD, Mirković MD, Nikolić NS, Stanković D, Mijin DŽ, Kapor A. Influence of the weak interaction on the structure of metallocycle in binuclear copper(II) complex. in PHYSICAL CHEMISTRY 2014: 12th International Conference on Fundamental and Applied Aspects of Physical Chemistry. 2014;M-05-P..
Tomić, Zoran D., Mirković, Marija D., Nikolić, Nadežda S., Stanković, Dragana, Mijin, Dušan Ž., Kapor, Agneš, "Influence of the weak interaction on the structure of metallocycle in binuclear copper(II) complex" in PHYSICAL CHEMISTRY 2014: 12th International Conference on Fundamental and Applied Aspects of Physical Chemistry, M-05-P (2014).

CH/pi interactions in metal-porphyrin complexes with pyrrole and chelate rings as hydrogen acceptors

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

(2012)

TY  - JOUR
AU  - Medaković, Vesna B.
AU  - Bogdanović, Goran A.
AU  - Milčić, Miloš K.
AU  - Janjić, Goran V.
AU  - Zarić, Snežana D.
PY  - 2012
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/5184
AB  - CH/pi interactions in metal porphyrinato complexes were studied by analyzing data in crystal structures from the Cambridge Structural Database (CSD) and by quantum chemical calculations. The analysis of the data in the CSD shows that both five-membered pyrrole and six-membered chelate rings form CH/pi interactions. The interactions occur more frequently with five-membered rings. The analysis of distances in crystal structures and calculated energies show stronger interactions with six-membered chelate rings, indicating that a larger number of interactions with five-membered rings are not the consequence of stronger interactions, but better accessibility of five-membered pyrrole rings. The calculated energies of the interactions with positions in six-membered rings are -2.09 to -2.83 kcal/mol, while the energies with five-membered rings are -2.05 to -2.26 kcal/mol. The results reveal that stronger interactions of six-membered rings are the consequence of stronger electrostatic interactions. Substituents on the porphyrin ring significantly strengthen the interactions. Substituents on the six-membered ring strengthen the interaction energy by about 20%. The results show that CH/pi interactions play an important role in molecular recognition of metalloporphyrins. The significant influence of the substituents on interaction energies can be very important for the design of model systems in bioinorganic chemistry. (C) 2012 Elsevier Inc. All rights reserved.
T2  - Journal of Inorganic Biochemistry
T1  - CH/pi interactions in metal-porphyrin complexes with pyrrole and chelate rings as hydrogen acceptors
VL  - 117
SP  - 157
EP  - 163
DO  - 10.1016/j.jinorgbio.2012.09.002
ER  - 
@article{
author = "Medaković, Vesna B. and Bogdanović, Goran A. and Milčić, Miloš K. and Janjić, Goran V. and Zarić, Snežana D.",
year = "2012",
abstract = "CH/pi interactions in metal porphyrinato complexes were studied by analyzing data in crystal structures from the Cambridge Structural Database (CSD) and by quantum chemical calculations. The analysis of the data in the CSD shows that both five-membered pyrrole and six-membered chelate rings form CH/pi interactions. The interactions occur more frequently with five-membered rings. The analysis of distances in crystal structures and calculated energies show stronger interactions with six-membered chelate rings, indicating that a larger number of interactions with five-membered rings are not the consequence of stronger interactions, but better accessibility of five-membered pyrrole rings. The calculated energies of the interactions with positions in six-membered rings are -2.09 to -2.83 kcal/mol, while the energies with five-membered rings are -2.05 to -2.26 kcal/mol. The results reveal that stronger interactions of six-membered rings are the consequence of stronger electrostatic interactions. Substituents on the porphyrin ring significantly strengthen the interactions. Substituents on the six-membered ring strengthen the interaction energy by about 20%. The results show that CH/pi interactions play an important role in molecular recognition of metalloporphyrins. The significant influence of the substituents on interaction energies can be very important for the design of model systems in bioinorganic chemistry. (C) 2012 Elsevier Inc. All rights reserved.",
journal = "Journal of Inorganic Biochemistry",
title = "CH/pi interactions in metal-porphyrin complexes with pyrrole and chelate rings as hydrogen acceptors",
volume = "117",
pages = "157-163",
doi = "10.1016/j.jinorgbio.2012.09.002"
}
Medaković, V. B., Bogdanović, G. A., Milčić, M. K., Janjić, G. V.,& Zarić, S. D.. (2012). CH/pi interactions in metal-porphyrin complexes with pyrrole and chelate rings as hydrogen acceptors. in Journal of Inorganic Biochemistry, 117, 157-163.
https://doi.org/10.1016/j.jinorgbio.2012.09.002
Medaković VB, Bogdanović GA, Milčić MK, Janjić GV, Zarić SD. CH/pi interactions in metal-porphyrin complexes with pyrrole and chelate rings as hydrogen acceptors. in Journal of Inorganic Biochemistry. 2012;117:157-163.
doi:10.1016/j.jinorgbio.2012.09.002 .
Medaković, Vesna B., Bogdanović, Goran A., Milčić, Miloš K., Janjić, Goran V., Zarić, Snežana D., "CH/pi interactions in metal-porphyrin complexes with pyrrole and chelate rings as hydrogen acceptors" in Journal of Inorganic Biochemistry, 117 (2012):157-163,
https://doi.org/10.1016/j.jinorgbio.2012.09.002 . .
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Parallel stacking interactions in square-planar transition-metal complexes containing fused chelate and C-6-aromatic rings

Sredojević, Dušan; Vojislavljevic, Dubravka Z.; Tomić, Zoran D.; Zarić, Snežana D.

(2012)

TY  - JOUR
AU  - Sredojević, Dušan
AU  - Vojislavljevic, Dubravka Z.
AU  - Tomić, Zoran D.
AU  - Zarić, Snežana D.
PY  - 2012
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/4856
AB  - Stacking interactions in the crystal structures of square-planar transition metal complexes from the Cambridge Structural Database with five-and six-membered chelate rings fused with C6-arom rings (arom = aromatic) were analyzed. The distribution of distances between the closest C6-arom-C6-arom and C6-arom-chelate contacts shows that in a large fraction of the intermolecular interactions the C6-arom ring of one molecule is closer to the chelate than to the C6-arom ring of the other molecule. These results indicate a possible preference of the C6-arom ring to form stacking contacts with the chelate rings. The preference is ubiquitous and does not depend on the metal type.
T2  - Acta Crystallographica. Section B: Structural Science
T1  - Parallel stacking interactions in square-planar transition-metal complexes containing fused chelate and C-6-aromatic rings
VL  - 68
SP  - 261
EP  - 265
DO  - 10.1107/S0108768112012281
ER  - 
@article{
author = "Sredojević, Dušan and Vojislavljevic, Dubravka Z. and Tomić, Zoran D. and Zarić, Snežana D.",
year = "2012",
abstract = "Stacking interactions in the crystal structures of square-planar transition metal complexes from the Cambridge Structural Database with five-and six-membered chelate rings fused with C6-arom rings (arom = aromatic) were analyzed. The distribution of distances between the closest C6-arom-C6-arom and C6-arom-chelate contacts shows that in a large fraction of the intermolecular interactions the C6-arom ring of one molecule is closer to the chelate than to the C6-arom ring of the other molecule. These results indicate a possible preference of the C6-arom ring to form stacking contacts with the chelate rings. The preference is ubiquitous and does not depend on the metal type.",
journal = "Acta Crystallographica. Section B: Structural Science",
title = "Parallel stacking interactions in square-planar transition-metal complexes containing fused chelate and C-6-aromatic rings",
volume = "68",
pages = "261-265",
doi = "10.1107/S0108768112012281"
}
Sredojević, D., Vojislavljevic, D. Z., Tomić, Z. D.,& Zarić, S. D.. (2012). Parallel stacking interactions in square-planar transition-metal complexes containing fused chelate and C-6-aromatic rings. in Acta Crystallographica. Section B: Structural Science, 68, 261-265.
https://doi.org/10.1107/S0108768112012281
Sredojević D, Vojislavljevic DZ, Tomić ZD, Zarić SD. Parallel stacking interactions in square-planar transition-metal complexes containing fused chelate and C-6-aromatic rings. in Acta Crystallographica. Section B: Structural Science. 2012;68:261-265.
doi:10.1107/S0108768112012281 .
Sredojević, Dušan, Vojislavljevic, Dubravka Z., Tomić, Zoran D., Zarić, Snežana D., "Parallel stacking interactions in square-planar transition-metal complexes containing fused chelate and C-6-aromatic rings" in Acta Crystallographica. Section B: Structural Science, 68 (2012):261-265,
https://doi.org/10.1107/S0108768112012281 . .
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