Halogen bonds as a tool in the design of high energetic materials: evidence from crystal structures and quantum chemical calculations
Abstract
Positive electrostatic potential over the central area of the molecular surface is one of the main characteristics of high energetic materials (HEMs) that determines their sensitivity towards detonation. The influence of halogen bonds on the values of the electrostatic potential of selected HEM molecules was studied in crystal structures extracted from the Cambridge Structural Database and by quantum chemical calculations. Analysis of halogen bonds in crystal structures containing halogen-substituted 2,4,6-trinitrophenyl fragments showed that these groups form halogen bonds (183 contacts). Analysis of electrostatic potential maps calculated for geometries of non-halogen bonded and halogen bonded HEM molecules extracted from crystal structures showed that halogen bonding modifies electrostatic potential in the centers of these compounds. Since in selected crystal structures other types of non-covalent interactions were also present, quantum chemical calculations on model systems were us...ed to reveal and quantitatively describe the influence of halogen bonds on the electrostatic potential of selected HEM molecules. These results could be used for the design of new classes of halogen-containing high energetic molecules with reduced sensitivities towards detonation.
Source:
CrystEngComm, 2021, 23, 39, 6915-6922Publisher:
- Royal Society of Chemistry
Funding / projects:
- Ministry of Science, Technological Development and Innovation of the Republic of Serbia, institutional funding - 200168 (University of Belgrade, Faculty of Chemistry) (RS-MESTD-inst-2020-200168)
- Ministry of Science, Technological Development and Innovation of the Republic of Serbia, institutional funding - 200288 (Innovation Center of the Faculty of Chemistry) (RS-MESTD-inst-2020-200288)
Note:
- Supplementary material: https://cherry.chem.bg.ac.rs/handle/123456789/4751
Related info:
- Referenced by
https://cherry.chem.bg.ac.rs/handle/123456789/4751
DOI: 10.1039/D1CE00854D
ISSN: 1466-8033
WoS: 000695964800001
Scopus: 2-s2.0-85117024500
Collections
Institution/Community
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Đunović, Aleksandra B. AU - Veljković, Dušan Ž. PY - 2021 UR - https://cherry.chem.bg.ac.rs/handle/123456789/4750 AB - Positive electrostatic potential over the central area of the molecular surface is one of the main characteristics of high energetic materials (HEMs) that determines their sensitivity towards detonation. The influence of halogen bonds on the values of the electrostatic potential of selected HEM molecules was studied in crystal structures extracted from the Cambridge Structural Database and by quantum chemical calculations. Analysis of halogen bonds in crystal structures containing halogen-substituted 2,4,6-trinitrophenyl fragments showed that these groups form halogen bonds (183 contacts). Analysis of electrostatic potential maps calculated for geometries of non-halogen bonded and halogen bonded HEM molecules extracted from crystal structures showed that halogen bonding modifies electrostatic potential in the centers of these compounds. Since in selected crystal structures other types of non-covalent interactions were also present, quantum chemical calculations on model systems were used to reveal and quantitatively describe the influence of halogen bonds on the electrostatic potential of selected HEM molecules. These results could be used for the design of new classes of halogen-containing high energetic molecules with reduced sensitivities towards detonation. PB - Royal Society of Chemistry T2 - CrystEngComm T1 - Halogen bonds as a tool in the design of high energetic materials: evidence from crystal structures and quantum chemical calculations VL - 23 IS - 39 SP - 6915 EP - 6922 DO - 10.1039/D1CE00854D ER -
@article{ author = "Đunović, Aleksandra B. and Veljković, Dušan Ž.", year = "2021", abstract = "Positive electrostatic potential over the central area of the molecular surface is one of the main characteristics of high energetic materials (HEMs) that determines their sensitivity towards detonation. The influence of halogen bonds on the values of the electrostatic potential of selected HEM molecules was studied in crystal structures extracted from the Cambridge Structural Database and by quantum chemical calculations. Analysis of halogen bonds in crystal structures containing halogen-substituted 2,4,6-trinitrophenyl fragments showed that these groups form halogen bonds (183 contacts). Analysis of electrostatic potential maps calculated for geometries of non-halogen bonded and halogen bonded HEM molecules extracted from crystal structures showed that halogen bonding modifies electrostatic potential in the centers of these compounds. Since in selected crystal structures other types of non-covalent interactions were also present, quantum chemical calculations on model systems were used to reveal and quantitatively describe the influence of halogen bonds on the electrostatic potential of selected HEM molecules. These results could be used for the design of new classes of halogen-containing high energetic molecules with reduced sensitivities towards detonation.", publisher = "Royal Society of Chemistry", journal = "CrystEngComm", title = "Halogen bonds as a tool in the design of high energetic materials: evidence from crystal structures and quantum chemical calculations", volume = "23", number = "39", pages = "6915-6922", doi = "10.1039/D1CE00854D" }
Đunović, A. B.,& Veljković, D. Ž.. (2021). Halogen bonds as a tool in the design of high energetic materials: evidence from crystal structures and quantum chemical calculations. in CrystEngComm Royal Society of Chemistry., 23(39), 6915-6922. https://doi.org/10.1039/D1CE00854D
Đunović AB, Veljković DŽ. Halogen bonds as a tool in the design of high energetic materials: evidence from crystal structures and quantum chemical calculations. in CrystEngComm. 2021;23(39):6915-6922. doi:10.1039/D1CE00854D .
Đunović, Aleksandra B., Veljković, Dušan Ž., "Halogen bonds as a tool in the design of high energetic materials: evidence from crystal structures and quantum chemical calculations" in CrystEngComm, 23, no. 39 (2021):6915-6922, https://doi.org/10.1039/D1CE00854D . .