Aromaticity of Diazaborines and Their Protonated Forms
Само за регистроване кориснике
2016
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
Substitution of a CH group in benzene with nitrogen has a little effect on its aromaticity (Wang et al, Org. Lett. 2010, 12, 4824). How does the same type of substitution affect aromatic character of the three isomeric azaborines? Does further protonation change aromaticity of diazaborines? This work is aimed at answering these questions. Such a knowledge should be of interest for further exploration and application of BN/CC isosterism. Aromaticity of diazaborines and their protonated forms is studied with the aid of four aromaticity indices, HOMA, NICS(0)(pi zz), PDI and ECRE. Generally, NICS(0)(pi zz) and PDI point to similar aromaticity of diazaborines and their parent azaborines, while HOMA and ECRE indicate some changes. Thus, aromaticity of 1,2-azaborine slightly decreases/increases when CH meta/ortho,para to B is substituted with nitrogen. Aromaticity of the most aromatic 1,3-azaborine remains almost unchanged when CH meta to B and N is replaced with nitrogen, and becomes slight...ly weaker when any other CH group is substituted with nitrogen. Replacement of the CH ortho to N in 1,4-azaborine does not change much its cyclic delocalization, while replacement of the CH ortho to B leads to smaller cyclic delocalization. Protonated forms are either of similar or decreased aromaticity compared with neutral molecules.
Извор:
Journal of Organic Chemistry, 2016, 81, 1, 197-205Издавач:
- American Chemical Society (ACS)
Финансирање / пројекти:
- Експериментална и теоријска проучавања реактивности и биолошка активност стереодефинисаних тиазолидина и синтетичких аналога (RS-MESTD-Basic Research (BR or ON)-172020)
DOI: 10.1021/acs.joc.5b02499
ISSN: 0022-3263
PubMed: 26625099
WoS: 000367701900021
Scopus: 2-s2.0-84953403666
Институција/група
IHTMTY - JOUR AU - Stojanović, Milovan AU - Baranac-Stojanović, Marija PY - 2016 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/1974 AB - Substitution of a CH group in benzene with nitrogen has a little effect on its aromaticity (Wang et al, Org. Lett. 2010, 12, 4824). How does the same type of substitution affect aromatic character of the three isomeric azaborines? Does further protonation change aromaticity of diazaborines? This work is aimed at answering these questions. Such a knowledge should be of interest for further exploration and application of BN/CC isosterism. Aromaticity of diazaborines and their protonated forms is studied with the aid of four aromaticity indices, HOMA, NICS(0)(pi zz), PDI and ECRE. Generally, NICS(0)(pi zz) and PDI point to similar aromaticity of diazaborines and their parent azaborines, while HOMA and ECRE indicate some changes. Thus, aromaticity of 1,2-azaborine slightly decreases/increases when CH meta/ortho,para to B is substituted with nitrogen. Aromaticity of the most aromatic 1,3-azaborine remains almost unchanged when CH meta to B and N is replaced with nitrogen, and becomes slightly weaker when any other CH group is substituted with nitrogen. Replacement of the CH ortho to N in 1,4-azaborine does not change much its cyclic delocalization, while replacement of the CH ortho to B leads to smaller cyclic delocalization. Protonated forms are either of similar or decreased aromaticity compared with neutral molecules. PB - American Chemical Society (ACS) T2 - Journal of Organic Chemistry T1 - Aromaticity of Diazaborines and Their Protonated Forms VL - 81 IS - 1 SP - 197 EP - 205 DO - 10.1021/acs.joc.5b02499 ER -
@article{ author = "Stojanović, Milovan and Baranac-Stojanović, Marija", year = "2016", abstract = "Substitution of a CH group in benzene with nitrogen has a little effect on its aromaticity (Wang et al, Org. Lett. 2010, 12, 4824). How does the same type of substitution affect aromatic character of the three isomeric azaborines? Does further protonation change aromaticity of diazaborines? This work is aimed at answering these questions. Such a knowledge should be of interest for further exploration and application of BN/CC isosterism. Aromaticity of diazaborines and their protonated forms is studied with the aid of four aromaticity indices, HOMA, NICS(0)(pi zz), PDI and ECRE. Generally, NICS(0)(pi zz) and PDI point to similar aromaticity of diazaborines and their parent azaborines, while HOMA and ECRE indicate some changes. Thus, aromaticity of 1,2-azaborine slightly decreases/increases when CH meta/ortho,para to B is substituted with nitrogen. Aromaticity of the most aromatic 1,3-azaborine remains almost unchanged when CH meta to B and N is replaced with nitrogen, and becomes slightly weaker when any other CH group is substituted with nitrogen. Replacement of the CH ortho to N in 1,4-azaborine does not change much its cyclic delocalization, while replacement of the CH ortho to B leads to smaller cyclic delocalization. Protonated forms are either of similar or decreased aromaticity compared with neutral molecules.", publisher = "American Chemical Society (ACS)", journal = "Journal of Organic Chemistry", title = "Aromaticity of Diazaborines and Their Protonated Forms", volume = "81", number = "1", pages = "197-205", doi = "10.1021/acs.joc.5b02499" }
Stojanović, M.,& Baranac-Stojanović, M.. (2016). Aromaticity of Diazaborines and Their Protonated Forms. in Journal of Organic Chemistry American Chemical Society (ACS)., 81(1), 197-205. https://doi.org/10.1021/acs.joc.5b02499
Stojanović M, Baranac-Stojanović M. Aromaticity of Diazaborines and Their Protonated Forms. in Journal of Organic Chemistry. 2016;81(1):197-205. doi:10.1021/acs.joc.5b02499 .
Stojanović, Milovan, Baranac-Stojanović, Marija, "Aromaticity of Diazaborines and Their Protonated Forms" in Journal of Organic Chemistry, 81, no. 1 (2016):197-205, https://doi.org/10.1021/acs.joc.5b02499 . .