D2BIA—flexible, not (explicitly) arbitrary and reference/structurally invariant—a very effective and improved version of the D3BIA aromaticity index

Firme, Caio Lima; Araújo, Diógenes Mendes

D2BIA—flexible, not (explicitly) arbitrary and reference/structurally invariant—a very effective and improved version of the D3BIA aromaticity index

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dc.contributor.author	Firme, Caio Lima
dc.contributor.author	Araújo, Diógenes Mendes
dc.date.accessioned	2020-07-03T15:00:46Z
dc.date.available	2020-07-03T15:00:46Z
dc.date.issued	2017-08-07
dc.description.resumo	Although there are a multitude of aromaticity indexes, only a few have a widespread usage. All famous aro- maticity indexes are limited: HOMA and FLU are reference dependent; ELF is π-bond-dependent; PDI is structurally dependent and NICS is ring size dependent. These limitations stimulate the continuous search for better (i.e., having no dependency), more flexible (i.e., applied to any aromatic system) and more effective (i.e., with excellent correlations with other indexes) aromaticity indexes. The D3BIA was our first topological aromaticity index. It is flexible, reference-independent and effective for planar and caged aromatic molecules. However, one of its terms, the degree of degeneracy (δ), is arbitrary and difficult to carry out for new users hus, in this work, we show that D2BIA—an improved version of D3BIA—is a good candidate to be used widely, since it retains the strong points of D3BIA while avoiding its weak point. In particular cases where all studied systems have δ = 1 (e.g., for acenes), then D2BIA equals D3BIA. For our recent study with acenes, D3BIA (and, as a consequence, D2BIA) has (have) an excellent correlation with FLU according to the MP3 method. In this work, by using DFT calculations for a series involving several six-membered and five membered heteroaromatic rings, only D2BIA and NICS have very good correlation. All other well known aromaticity indexes used in this work (FLU, HOMA and ELF) gave poor correlations. As to homoaromatic systems, only D2BIA vs NICS and D2BIA vs FLU plots have excellent correlations. HOMA has the worst results in this series. Thus, D2BIA proved to be flexible and effective for the analysis of heteroaromatic rings of different sizes and for caged homoaromatic systems. Moreover, D2BIA has better correlations than D3BIA for planar aromatic systems, and same correlations for caged-homoaromatic systems	pt_BR
dc.identifier.citation	FIRME, Caio Lima; ARAÚJO, Diógenes Mendes. D2BIA—flexible, not (explicitly) arbitrary and reference/structurally invariant—a very effective and improved version of the D3BIA aromaticity index. Journal of Molecular Modeling, [S.l.], v.23, n. 9, p. 1-9, ago. 2017. Disponível em: https://link.springer.com/article/10.1007/s00894-017-3433-6. Acesso em: 18 jun. 2020.	pt_BR
dc.identifier.doi	10.1007/s00894-017-3433-6
dc.identifier.issn	0948-5023
dc.identifier.uri	https://repositorio.ufrn.br/jspui/handle/123456789/29431
dc.language	en	pt_BR
dc.publisher	Springer	pt_BR
dc.rights	Attribution 3.0 Brazil	*
dc.rights.uri	http://creativecommons.org/licenses/by/3.0/br/	*
dc.subject	D3BIA	pt_BR
dc.subject	D2BIA	pt_BR
dc.subject	Aromaticity index	pt_BR
dc.subject	QTAIM	pt_BR
dc.subject	Heteroaromatic rings	pt_BR
dc.subject	Homoaromaticity	pt_BR
dc.subject	NICS	pt_BR
dc.title	D2BIA—flexible, not (explicitly) arbitrary and reference/structurally invariant—a very effective and improved version of the D3BIA aromaticity index	pt_BR
dc.type	article	pt_BR