Cyclic pi Electron De localization in Fluoroborazines
Abstract
How does the most electronegative atom, fluorine, affect cyclic pi electron delocalization (aromaticity) of an inorganic counterpart of benzene, borazine? Previous studies have shown that N-fluorination decreases the aromatic character, whereas conclusions about the effect of B-fluorination oppose each other (I. Phys. Chem. A 1997, 101, 9410 and J. Mol. Struct.: THEOCHEM 2005, 715, 91). The aim of this study is to resolve this discrepancy and also to evaluate a degree of cyclic pi electron delocalization in all possible polyfluoroborazines. This was done by employing four aromaticity indices, HOMA, NICS, ECRE, and PDI. NICS, ECRE, and PDI gave a satisfactory description of aromaticity of the studied molecules. It was found that N-monofluoroborazine, N-difluoroborazine, and N-trifluoroborazine are the only fluorinated derivatives that exhibit a higher degree of aromaticity compared to borazine. This result opposes the previous ones regarding the influence of N-fluorination.
Source:
Journal of Physical Chemistry. Part A: Molecules, Spectroscopy, Kinetics, Environment and General Th, 2013, 117, 45, 11540-11547Publisher:
- Amer Chemical Soc, Washington
Funding / projects:
- Experimental and theoretical study of reactivity and biological activity of stereodefined thiazolidines and their synthetic analogues (RS-MESTD-Basic Research (BR or ON)-172020)
Note:
- Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3480
DOI: 10.1021/jp407454x
ISSN: 1089-5639
PubMed: 24144357
WoS: 000327111400017
Scopus: 2-s2.0-84887884068
Collections
Institution/Community
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Baranac-Stojanović, Marija PY - 2013 UR - https://cherry.chem.bg.ac.rs/handle/123456789/1442 AB - How does the most electronegative atom, fluorine, affect cyclic pi electron delocalization (aromaticity) of an inorganic counterpart of benzene, borazine? Previous studies have shown that N-fluorination decreases the aromatic character, whereas conclusions about the effect of B-fluorination oppose each other (I. Phys. Chem. A 1997, 101, 9410 and J. Mol. Struct.: THEOCHEM 2005, 715, 91). The aim of this study is to resolve this discrepancy and also to evaluate a degree of cyclic pi electron delocalization in all possible polyfluoroborazines. This was done by employing four aromaticity indices, HOMA, NICS, ECRE, and PDI. NICS, ECRE, and PDI gave a satisfactory description of aromaticity of the studied molecules. It was found that N-monofluoroborazine, N-difluoroborazine, and N-trifluoroborazine are the only fluorinated derivatives that exhibit a higher degree of aromaticity compared to borazine. This result opposes the previous ones regarding the influence of N-fluorination. PB - Amer Chemical Soc, Washington T2 - Journal of Physical Chemistry. Part A: Molecules, Spectroscopy, Kinetics, Environment and General Th T1 - Cyclic pi Electron De localization in Fluoroborazines VL - 117 IS - 45 SP - 11540 EP - 11547 DO - 10.1021/jp407454x ER -
@article{ author = "Baranac-Stojanović, Marija", year = "2013", abstract = "How does the most electronegative atom, fluorine, affect cyclic pi electron delocalization (aromaticity) of an inorganic counterpart of benzene, borazine? Previous studies have shown that N-fluorination decreases the aromatic character, whereas conclusions about the effect of B-fluorination oppose each other (I. Phys. Chem. A 1997, 101, 9410 and J. Mol. Struct.: THEOCHEM 2005, 715, 91). The aim of this study is to resolve this discrepancy and also to evaluate a degree of cyclic pi electron delocalization in all possible polyfluoroborazines. This was done by employing four aromaticity indices, HOMA, NICS, ECRE, and PDI. NICS, ECRE, and PDI gave a satisfactory description of aromaticity of the studied molecules. It was found that N-monofluoroborazine, N-difluoroborazine, and N-trifluoroborazine are the only fluorinated derivatives that exhibit a higher degree of aromaticity compared to borazine. This result opposes the previous ones regarding the influence of N-fluorination.", publisher = "Amer Chemical Soc, Washington", journal = "Journal of Physical Chemistry. Part A: Molecules, Spectroscopy, Kinetics, Environment and General Th", title = "Cyclic pi Electron De localization in Fluoroborazines", volume = "117", number = "45", pages = "11540-11547", doi = "10.1021/jp407454x" }
Baranac-Stojanović, M.. (2013). Cyclic pi Electron De localization in Fluoroborazines. in Journal of Physical Chemistry. Part A: Molecules, Spectroscopy, Kinetics, Environment and General Th Amer Chemical Soc, Washington., 117(45), 11540-11547. https://doi.org/10.1021/jp407454x
Baranac-Stojanović M. Cyclic pi Electron De localization in Fluoroborazines. in Journal of Physical Chemistry. Part A: Molecules, Spectroscopy, Kinetics, Environment and General Th. 2013;117(45):11540-11547. doi:10.1021/jp407454x .
Baranac-Stojanović, Marija, "Cyclic pi Electron De localization in Fluoroborazines" in Journal of Physical Chemistry. Part A: Molecules, Spectroscopy, Kinetics, Environment and General Th, 117, no. 45 (2013):11540-11547, https://doi.org/10.1021/jp407454x . .