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 . .

TY  - CONF
AU  - Medaković, Vesna B.
AU  - Milčić, Miloš K.
AU  - Bogdanović, Goran A.
PY  - 2006
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/9473
AB  - The Cambridge Structural Database (CSD) was screened in order to find and investigate specific C−H⋅⋅⋅π interactions between C−H groups and two types of rings with delocalized π-bonds that exist in porphyrin: pyrrole and six-membered chelate. Statistical analysis of geometrical parameters for interactions in both types of rings was done. In order to determine preferred positions in porphyrinato ring for C−H⋅⋅⋅π interactions fifteen different points distributed over porphyrin ring have been chosen and each of them have been analyzed. Calculations of these interactions by density functional theory (DFT) have been done on three different model systems.
PB  - Society of Physical Chemists of Serbia
C3  - Physical chemistry 2006: 8th international conference on fundemental and applied aspract of physical chemistry
T1  - Study of C−H⋅⋅⋅π interactions with pyrrole and chelate rings in metal-porphyrin complexes
SP  - 701
EP  - 703
UR  - https://hdl.handle.net/21.15107/rcub_vinar_9473
ER  - 

@conference{
author = "Medaković, Vesna B. and Milčić, Miloš K. and Bogdanović, Goran A.",
year = "2006",
abstract = "The Cambridge Structural Database (CSD) was screened in order to find and investigate specific C−H⋅⋅⋅π interactions between C−H groups and two types of rings with delocalized π-bonds that exist in porphyrin: pyrrole and six-membered chelate. Statistical analysis of geometrical parameters for interactions in both types of rings was done. In order to determine preferred positions in porphyrinato ring for C−H⋅⋅⋅π interactions fifteen different points distributed over porphyrin ring have been chosen and each of them have been analyzed. Calculations of these interactions by density functional theory (DFT) have been done on three different model systems.",
publisher = "Society of Physical Chemists of Serbia",
journal = "Physical chemistry 2006: 8th international conference on fundemental and applied aspract of physical chemistry",
title = "Study of C−H⋅⋅⋅π interactions with pyrrole and chelate rings in metal-porphyrin complexes",
pages = "701-703",
url = "https://hdl.handle.net/21.15107/rcub_vinar_9473"
}

Medaković, V. B., Milčić, M. K.,& Bogdanović, G. A.. (2006). Study of C−H⋅⋅⋅π interactions with pyrrole and chelate rings in metal-porphyrin complexes. in Physical chemistry 2006: 8th international conference on fundemental and applied aspract of physical chemistry
Society of Physical Chemists of Serbia., 701-703.
https://hdl.handle.net/21.15107/rcub_vinar_9473

Medaković VB, Milčić MK, Bogdanović GA. Study of C−H⋅⋅⋅π interactions with pyrrole and chelate rings in metal-porphyrin complexes. in Physical chemistry 2006: 8th international conference on fundemental and applied aspract of physical chemistry. 2006;:701-703.
https://hdl.handle.net/21.15107/rcub_vinar_9473 .

Medaković, Vesna B., Milčić, Miloš K., Bogdanović, Goran A., "Study of C−H⋅⋅⋅π interactions with pyrrole and chelate rings in metal-porphyrin complexes" in Physical chemistry 2006: 8th international conference on fundemental and applied aspract of physical chemistry (2006):701-703,
https://hdl.handle.net/21.15107/rcub_vinar_9473 .

TY  - JOUR
AU  - Bogdanović, Goran A.
AU  - Medaković, Vesna B.
AU  - Milčić, Miloš K.
AU  - Zarić, Snežana D.
PY  - 2004
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/6486
AB  - Cambridge Structural Database (CSD) was screened in order to find intramolecular C-H...pi interactions with a chelate ring of coordinated porphyrin. It was found 154 crystal structures with 244 intramolecular C-H...pi interactions in transition metal complexes with derivatives of porphyrin. Comparison of interacting distances indicates that interactions of hydrogen atoms in positions 2 and 6 of axially coordinated pyridine are more favorable with ruffled than with planar porphyrin.
T2  - International Journal of Molecular Sciences
T1  - Intramolecular C-H center dot center dot center dot pi interactions in metal-porphyrin complexes
VL  - 5
SP  - 174
EP  - 185
DO  - 10.3390/i5040174
ER  - 

@article{
author = "Bogdanović, Goran A. and Medaković, Vesna B. and Milčić, Miloš K. and Zarić, Snežana D.",
year = "2004",
abstract = "Cambridge Structural Database (CSD) was screened in order to find intramolecular C-H...pi interactions with a chelate ring of coordinated porphyrin. It was found 154 crystal structures with 244 intramolecular C-H...pi interactions in transition metal complexes with derivatives of porphyrin. Comparison of interacting distances indicates that interactions of hydrogen atoms in positions 2 and 6 of axially coordinated pyridine are more favorable with ruffled than with planar porphyrin.",
journal = "International Journal of Molecular Sciences",
title = "Intramolecular C-H center dot center dot center dot pi interactions in metal-porphyrin complexes",
volume = "5",
pages = "174-185",
doi = "10.3390/i5040174"
}

Bogdanović, G. A., Medaković, V. B., Milčić, M. K.,& Zarić, S. D.. (2004). Intramolecular C-H center dot center dot center dot pi interactions in metal-porphyrin complexes. in International Journal of Molecular Sciences, 5, 174-185.
https://doi.org/10.3390/i5040174

Bogdanović GA, Medaković VB, Milčić MK, Zarić SD. Intramolecular C-H center dot center dot center dot pi interactions in metal-porphyrin complexes. in International Journal of Molecular Sciences. 2004;5:174-185.
doi:10.3390/i5040174 .

Bogdanović, Goran A., Medaković, Vesna B., Milčić, Miloš K., Zarić, Snežana D., "Intramolecular C-H center dot center dot center dot pi interactions in metal-porphyrin complexes" in International Journal of Molecular Sciences, 5 (2004):174-185,
https://doi.org/10.3390/i5040174 . .

TY  - CONF
AU  - Medaković, Vesna B.
AU  - Milčić, Miloš K.
AU  - Zarić, Snežana D.
PY  - 2004
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/9597
AB  - Specific C − H···π interactions with the π-system of porphyrinato chelate ring were found in crystal structures of transition metal complexes from the CSD and statistical analysis of geometrical parameters for intramolecular and intermolecular interactions was done. DFT calculations on a model system show that energy of the interaction is 1.58 kcal/mol and that the strongest interaction occurs when the distance between hydrogen atom and the center of the chelate ring is 2.6 Å. This prediction is in good agreement with the distances for intermolecular interactions found in the crystal structures. In many cases the intramolecular interaction distances are much shorter than 2.6 Å, and these short distances appear to be caused by geometrical constrains. The C − H···π interactions with chelate ring of porphyrinato ligand can be important in biomolecules with porphyrin as they can influence the structure, contribute to the stability and play some role in function of biomolecules.
PB  - Society of Physical Chemists of Serbia
C3  - Physical chemistry 2004: 7th international conference on fundemental and applied aspract of physical chemistry
T1  - C − H···π interactions in the metal-porphyrin complexes with chelate ring as the h acceptor
VL  - 2
SP  - 763
EP  - 765
UR  - https://hdl.handle.net/21.15107/rcub_vinar_9597
ER  - 

@conference{
author = "Medaković, Vesna B. and Milčić, Miloš K. and Zarić, Snežana D.",
year = "2004",
abstract = "Specific C − H···π interactions with the π-system of porphyrinato chelate ring were found in crystal structures of transition metal complexes from the CSD and statistical analysis of geometrical parameters for intramolecular and intermolecular interactions was done. DFT calculations on a model system show that energy of the interaction is 1.58 kcal/mol and that the strongest interaction occurs when the distance between hydrogen atom and the center of the chelate ring is 2.6 Å. This prediction is in good agreement with the distances for intermolecular interactions found in the crystal structures. In many cases the intramolecular interaction distances are much shorter than 2.6 Å, and these short distances appear to be caused by geometrical constrains. The C − H···π interactions with chelate ring of porphyrinato ligand can be important in biomolecules with porphyrin as they can influence the structure, contribute to the stability and play some role in function of biomolecules.",
publisher = "Society of Physical Chemists of Serbia",
journal = "Physical chemistry 2004: 7th international conference on fundemental and applied aspract of physical chemistry",
title = "C − H···π interactions in the metal-porphyrin complexes with chelate ring as the h acceptor",
volume = "2",
pages = "763-765",
url = "https://hdl.handle.net/21.15107/rcub_vinar_9597"
}

Medaković, V. B., Milčić, M. K.,& Zarić, S. D.. (2004). C − H···π interactions in the metal-porphyrin complexes with chelate ring as the h acceptor. in Physical chemistry 2004: 7th international conference on fundemental and applied aspract of physical chemistry
Society of Physical Chemists of Serbia., 2, 763-765.
https://hdl.handle.net/21.15107/rcub_vinar_9597

Medaković VB, Milčić MK, Zarić SD. C − H···π interactions in the metal-porphyrin complexes with chelate ring as the h acceptor. in Physical chemistry 2004: 7th international conference on fundemental and applied aspract of physical chemistry. 2004;2:763-765.
https://hdl.handle.net/21.15107/rcub_vinar_9597 .

Medaković, Vesna B., Milčić, Miloš K., Zarić, Snežana D., "C − H···π interactions in the metal-porphyrin complexes with chelate ring as the h acceptor" in Physical chemistry 2004: 7th international conference on fundemental and applied aspract of physical chemistry, 2 (2004):763-765,
https://hdl.handle.net/21.15107/rcub_vinar_9597 .

TY  - JOUR
AU  - Medaković, Vesna B.
AU  - Milčić, Miloš K.
AU  - Bogdanović, Goran A.
AU  - Zarić, Snežana D.
PY  - 2004
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/2818
AB  - Specific C-H(...)pi interactions with the pi-system of porphyrinato chelate ring were found in crystal structures of transition metal complexes from the Cambridge Structural Database and statistical analysis of geometrical parameters for intramolecular and intermolecular interactions was done. By density functional theory calculations on a model system it was evaluated that an interaction energy is above 1.5 kcal/mol and that the strongest interaction occurs when the distance between hydrogen atom and the center of the chelate ring is 2.6 Angstrom. This prediction is in good agreement with the distances for intermolecular interactions found in the crystal structures. In many cases the intramolecular interaction distances are much shorter than 2.6 Angstrom, and these short distances are caused by geometrical constrains. The C-H(...)pi interactions with chelate ring of porphyrinato ligand can influence the structure, contribute to its stability, and play some role in the function of biomolecules with metalo porphyrins. (C) 2004 Elsevier Inc. All rights reserved.
T2  - Journal of Inorganic Biochemistry
T1  - C-H center dot center dot center dot pi interactions in the metal-porphyrin complexes with chelate ring as the H acceptor
VL  - 98
IS  - 11
SP  - 1867
EP  - 1873
DO  - 10.1016/j.jinorgbio.2004.08.012
ER  - 

@article{
author = "Medaković, Vesna B. and Milčić, Miloš K. and Bogdanović, Goran A. and Zarić, Snežana D.",
year = "2004",
abstract = "Specific C-H(...)pi interactions with the pi-system of porphyrinato chelate ring were found in crystal structures of transition metal complexes from the Cambridge Structural Database and statistical analysis of geometrical parameters for intramolecular and intermolecular interactions was done. By density functional theory calculations on a model system it was evaluated that an interaction energy is above 1.5 kcal/mol and that the strongest interaction occurs when the distance between hydrogen atom and the center of the chelate ring is 2.6 Angstrom. This prediction is in good agreement with the distances for intermolecular interactions found in the crystal structures. In many cases the intramolecular interaction distances are much shorter than 2.6 Angstrom, and these short distances are caused by geometrical constrains. The C-H(...)pi interactions with chelate ring of porphyrinato ligand can influence the structure, contribute to its stability, and play some role in the function of biomolecules with metalo porphyrins. (C) 2004 Elsevier Inc. All rights reserved.",
journal = "Journal of Inorganic Biochemistry",
title = "C-H center dot center dot center dot pi interactions in the metal-porphyrin complexes with chelate ring as the H acceptor",
volume = "98",
number = "11",
pages = "1867-1873",
doi = "10.1016/j.jinorgbio.2004.08.012"
}

Medaković, V. B., Milčić, M. K., Bogdanović, G. A.,& Zarić, S. D.. (2004). C-H center dot center dot center dot pi interactions in the metal-porphyrin complexes with chelate ring as the H acceptor. in Journal of Inorganic Biochemistry, 98(11), 1867-1873.
https://doi.org/10.1016/j.jinorgbio.2004.08.012

Medaković VB, Milčić MK, Bogdanović GA, Zarić SD. C-H center dot center dot center dot pi interactions in the metal-porphyrin complexes with chelate ring as the H acceptor. in Journal of Inorganic Biochemistry. 2004;98(11):1867-1873.
doi:10.1016/j.jinorgbio.2004.08.012 .

Medaković, Vesna B., Milčić, Miloš K., Bogdanović, Goran A., Zarić, Snežana D., "C-H center dot center dot center dot pi interactions in the metal-porphyrin complexes with chelate ring as the H acceptor" in Journal of Inorganic Biochemistry, 98, no. 11 (2004):1867-1873,
https://doi.org/10.1016/j.jinorgbio.2004.08.012 . .