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Aromaticity of Diazaborines and Their Protonated Forms

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2016
Authors
Stojanović, Milovan
Baranac-Stojanović, Marija
Article (Published version)
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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 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.

Source:
Journal of Organic Chemistry, 2016, 81, 1, 197-205
Publisher:
  • Amer Chemical Soc, Washington
Projects:
  • Experimental and theoretical study of reactivity and biological activity of stereodefined thiazolidines and their synthetic analogues (RS-172020)

DOI: 10.1021/acs.joc.5b02499

ISSN: 0022-3263

PubMed: 26625099

WoS: 000367701900021

Scopus: 2-s2.0-84953403666
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URI
http://cer.ihtm.bg.ac.rs/handle/123456789/1974
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