TY  - JOUR
AU  - Bogdanović, Goran A.
AU  - Ostojić, Bojana
AU  - Novaković, Slađana B.
PY  - 2018
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/9896
AB  - Statistical analysis of data extracted from the Cambridge Structural Database (CSD) has been used to investigate the crystal structure properties of odialkoxybenzene derivatives, compounds containing two ether oxygen acceptors in ortho positions of benzene ring. It has been shown that in more than 90% of cases, the fragment has predictable geometrical characteristics where the two ether oxygens form short interatomic O center dot center dot center dot O contact (2.57 A in average), while O-substitutents take trans position, both approximately coplanar with the benzene ring. Such arrangement of oxygen acceptors produces a large and uniform area of the negative electrostatic potential suitable for multiple hydrogen bonding. The acceptor abilities of the O center dot center dot center dot O system have been investigated by the statistical CSD analysis. The ab initio estimation of the interaction energy in the dimer of o-dimethoxybenzene (DMB) and H2O, employed as a model system, is achieved via high-level electron correlation CCSD(T) calculation with the complete basis set extrapolation. The interaction energy is estimated to be 6.5 kcal/mol. The results indicate the existence of a very flat potential the region between methoxy oxygens and that DMB water is a highly flexible system. The structural role of the O center dot center dot center dot O acceptor system is particularly interesting considering its ability to form multiple hydrogen bonding
T2  - Crystal Growth and Design
T1  - Short Intramolecular O···O Contact in Some o-Dialkoxybenzene Derivatives Generates Efficient Hydrogen Bonding Acceptor Area
VL  - 18
IS  - 3
SP  - 1303
EP  - 1314
DO  - 10.1021/acs.cgd.7b00914
ER  - 

@article{
author = "Bogdanović, Goran A. and Ostojić, Bojana and Novaković, Slađana B.",
year = "2018",
abstract = "Statistical analysis of data extracted from the Cambridge Structural Database (CSD) has been used to investigate the crystal structure properties of odialkoxybenzene derivatives, compounds containing two ether oxygen acceptors in ortho positions of benzene ring. It has been shown that in more than 90% of cases, the fragment has predictable geometrical characteristics where the two ether oxygens form short interatomic O center dot center dot center dot O contact (2.57 A in average), while O-substitutents take trans position, both approximately coplanar with the benzene ring. Such arrangement of oxygen acceptors produces a large and uniform area of the negative electrostatic potential suitable for multiple hydrogen bonding. The acceptor abilities of the O center dot center dot center dot O system have been investigated by the statistical CSD analysis. The ab initio estimation of the interaction energy in the dimer of o-dimethoxybenzene (DMB) and H2O, employed as a model system, is achieved via high-level electron correlation CCSD(T) calculation with the complete basis set extrapolation. The interaction energy is estimated to be 6.5 kcal/mol. The results indicate the existence of a very flat potential the region between methoxy oxygens and that DMB water is a highly flexible system. The structural role of the O center dot center dot center dot O acceptor system is particularly interesting considering its ability to form multiple hydrogen bonding",
journal = "Crystal Growth and Design",
title = "Short Intramolecular O···O Contact in Some o-Dialkoxybenzene Derivatives Generates Efficient Hydrogen Bonding Acceptor Area",
volume = "18",
number = "3",
pages = "1303-1314",
doi = "10.1021/acs.cgd.7b00914"
}

Bogdanović, G. A., Ostojić, B.,& Novaković, S. B.. (2018). Short Intramolecular O···O Contact in Some o-Dialkoxybenzene Derivatives Generates Efficient Hydrogen Bonding Acceptor Area. in Crystal Growth and Design, 18(3), 1303-1314.
https://doi.org/10.1021/acs.cgd.7b00914

Bogdanović GA, Ostojić B, Novaković SB. Short Intramolecular O···O Contact in Some o-Dialkoxybenzene Derivatives Generates Efficient Hydrogen Bonding Acceptor Area. in Crystal Growth and Design. 2018;18(3):1303-1314.
doi:10.1021/acs.cgd.7b00914 .

Bogdanović, Goran A., Ostojić, Bojana, Novaković, Slađana B., "Short Intramolecular O···O Contact in Some o-Dialkoxybenzene Derivatives Generates Efficient Hydrogen Bonding Acceptor Area" in Crystal Growth and Design, 18, no. 3 (2018):1303-1314,
https://doi.org/10.1021/acs.cgd.7b00914 . .

TY  - JOUR
AU  - Francuski, Bojana M.
AU  - Novaković, Slađana B.
AU  - Ostojić, Bojana D.
AU  - Francuski, Đorđe D.
AU  - Bogdanović, Goran A.
PY  - 2015
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/671
AB  - Theoretical charge density analysis of the thioureido based compound 4-methyl-3-thiosemicarbazide (MeTSC) is used in this study with the aim to provide additional insight into electronic features of the thioureido sulfur acceptor and the corresponding D-H...S hydrogen bonding (D=N, C). The present work is motivated by our earlier experimental charge density study on the same compound that pointed out to a great flexibility of the thioureido S acceptor and its ability to adjust the lone pair electron density to the donor groups in simultaneous hydrogen bonding. Through the additional theoretical approach we were able to single out different fragments of MeTSC crystal and to carefully follow the changes in electron density properties of the S acceptors belonging to: isolated MeTSC monomers (i.e. two crystallographically independent molecules), eight D-H...S bonded dimers and MeTSC molecules placed in full crystal environment, where each S atom engages in four hydrogen bonds. Deformation density of the sulfurs lone electron pair, topological properties of D-H...S interactions and electrostatic potential are here examined in order to comprehend the mutual influence and potential cooperative effects of the four simultaneously formed interactions to each of the S acceptors. The hydrogen bonding involving thioureido S acceptor is also investigated in terms of the energetic properties of the eight real MeTSC dimers existing in the crystal structure, and additional systems MeTSC/MeOH and acetone/MeOH. The latter systems are designed with the purpose of direct comparison and ranking of interactions involving thioureido S to those involving more conventional, carbonyl O acceptor. Energetic features were thoroughly studied through electrostatic interactions energies (XD2006), cohesive energies (CRYSTAL09) and ab initio approach employing the coupled-cluster single S and doubles augmented by a perturbational correction for connected triple excitations (CCSD(T)) method. (C) 2015 Elsevier B.V. All rights reserved.
T2  - Computational and Theoretical Chemistry
T1  - Electronic features and hydrogen bonding capacity of the sulfur acceptor in thioureido-based compounds. Part 2. Further insight by theoretical charge density study
VL  - 1067
SP  - 93
EP  - 102
DO  - 10.1016/j.comptc.2015.05.024
ER  - 

@article{
author = "Francuski, Bojana M. and Novaković, Slađana B. and Ostojić, Bojana D. and Francuski, Đorđe D. and Bogdanović, Goran A.",
year = "2015",
abstract = "Theoretical charge density analysis of the thioureido based compound 4-methyl-3-thiosemicarbazide (MeTSC) is used in this study with the aim to provide additional insight into electronic features of the thioureido sulfur acceptor and the corresponding D-H...S hydrogen bonding (D=N, C). The present work is motivated by our earlier experimental charge density study on the same compound that pointed out to a great flexibility of the thioureido S acceptor and its ability to adjust the lone pair electron density to the donor groups in simultaneous hydrogen bonding. Through the additional theoretical approach we were able to single out different fragments of MeTSC crystal and to carefully follow the changes in electron density properties of the S acceptors belonging to: isolated MeTSC monomers (i.e. two crystallographically independent molecules), eight D-H...S bonded dimers and MeTSC molecules placed in full crystal environment, where each S atom engages in four hydrogen bonds. Deformation density of the sulfurs lone electron pair, topological properties of D-H...S interactions and electrostatic potential are here examined in order to comprehend the mutual influence and potential cooperative effects of the four simultaneously formed interactions to each of the S acceptors. The hydrogen bonding involving thioureido S acceptor is also investigated in terms of the energetic properties of the eight real MeTSC dimers existing in the crystal structure, and additional systems MeTSC/MeOH and acetone/MeOH. The latter systems are designed with the purpose of direct comparison and ranking of interactions involving thioureido S to those involving more conventional, carbonyl O acceptor. Energetic features were thoroughly studied through electrostatic interactions energies (XD2006), cohesive energies (CRYSTAL09) and ab initio approach employing the coupled-cluster single S and doubles augmented by a perturbational correction for connected triple excitations (CCSD(T)) method. (C) 2015 Elsevier B.V. All rights reserved.",
journal = "Computational and Theoretical Chemistry",
title = "Electronic features and hydrogen bonding capacity of the sulfur acceptor in thioureido-based compounds. Part 2. Further insight by theoretical charge density study",
volume = "1067",
pages = "93-102",
doi = "10.1016/j.comptc.2015.05.024"
}

Francuski, B. M., Novaković, S. B., Ostojić, B. D., Francuski, Đ. D.,& Bogdanović, G. A.. (2015). Electronic features and hydrogen bonding capacity of the sulfur acceptor in thioureido-based compounds. Part 2. Further insight by theoretical charge density study. in Computational and Theoretical Chemistry, 1067, 93-102.
https://doi.org/10.1016/j.comptc.2015.05.024

Francuski BM, Novaković SB, Ostojić BD, Francuski ĐD, Bogdanović GA. Electronic features and hydrogen bonding capacity of the sulfur acceptor in thioureido-based compounds. Part 2. Further insight by theoretical charge density study. in Computational and Theoretical Chemistry. 2015;1067:93-102.
doi:10.1016/j.comptc.2015.05.024 .

Francuski, Bojana M., Novaković, Slađana B., Ostojić, Bojana D., Francuski, Đorđe D., Bogdanović, Goran A., "Electronic features and hydrogen bonding capacity of the sulfur acceptor in thioureido-based compounds. Part 2. Further insight by theoretical charge density study" in Computational and Theoretical Chemistry, 1067 (2015):93-102,
https://doi.org/10.1016/j.comptc.2015.05.024 . .