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Aromaticity of Diazaborines and Their Protonated Forms

Overview of attention for article published in Journal of Organic Chemistry, December 2015
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Title
Aromaticity of Diazaborines and Their Protonated Forms
Published in
Journal of Organic Chemistry, December 2015
DOI 10.1021/acs.joc.5b02499
Pubmed ID
Authors

Milovan Stojanović, Marija Baranac-Stojanović

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.

Mendeley readers

The data shown below were compiled from readership statistics for 36 Mendeley readers of this research output. Click here to see the associated Mendeley record.

Geographical breakdown

Country Count As %
Unknown 36 100%

Demographic breakdown

Readers by professional status Count As %
Researcher 11 31%
Student > Ph. D. Student 7 19%
Professor 5 14%
Student > Master 5 14%
Student > Doctoral Student 2 6%
Other 3 8%
Unknown 3 8%
Readers by discipline Count As %
Chemistry 25 69%
Nursing and Health Professions 1 3%
Biochemistry, Genetics and Molecular Biology 1 3%
Pharmacology, Toxicology and Pharmaceutical Science 1 3%
Computer Science 1 3%
Other 2 6%
Unknown 5 14%

Attention Score in Context

This research output has an Altmetric Attention Score of 1. This is our high-level measure of the quality and quantity of online attention that it has received. This Attention Score, as well as the ranking and number of research outputs shown below, was calculated when the research output was last mentioned on 03 December 2015.
All research outputs
#10,907,537
of 12,308,406 outputs
Outputs from Journal of Organic Chemistry
#20,855
of 21,336 outputs
Outputs of similar age
#270,310
of 331,428 outputs
Outputs of similar age from Journal of Organic Chemistry
#97
of 103 outputs
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So far Altmetric has tracked 21,336 research outputs from this source. They receive a mean Attention Score of 4.1. This one is in the 1st percentile – i.e., 1% of its peers scored the same or lower than it.
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We're also able to compare this research output to 103 others from the same source and published within six weeks on either side of this one. This one is in the 1st percentile – i.e., 1% of its contemporaries scored the same or lower than it.