Evidence map›Paper›PMID 36385806›Full record

ArticleACS omega2022

Theoretical Investigation of Regiodivergent Addition of Anilines and Phenolates to

Haroldo C Da Silva, Talita O C Leite, Searitha C Rodrigues, Beatriz L C De Carvalho, Maria Tereza Martins, Rodolfo G Fiorot, Flaviana R F Dias, Vinícius R Campos, Vitor F Ferreira, Anna C Cunha and 1 more

Abstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in ACS omega, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

0numbers the graph read from it
0cells of the map it votes in
1citing papers in PubMed
–field-weighted citation impact
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

1 citing paper in PubMed.

  1. Article
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

11 authors.

Haroldo C Da SilvaLaboratório de Química Computacional e Modelagem Molecular, Departamento de Química Inorgânica, Universidade Federal Fluminense, Campus do Valonguinho, Outeiro de São João Batista, s/n, Niterói24020-150, RJ, Brazil.
Talita O C LeiteFaculdades Integradas Maria Thereza, Av. Visconde do Rio Branco, Niterói24020004, RJ, Brazil.
Searitha C RodriguesDepartamento de Química Orgânica, Universidade Federal Fluminense, Campus do Valonguinho, Outeiro de São João Batista, s/n, Niterói24020-141, RJ, Brazil.
Beatriz L C De CarvalhoDepartamento de Química Orgânica, Universidade Federal Fluminense, Campus do Valonguinho, Outeiro de São João Batista, s/n, Niterói24020-141, RJ, Brazil.
Maria Tereza MartinsDepartamento de Química Orgânica, Universidade Federal Fluminense, Campus do Valonguinho, Outeiro de São João Batista, s/n, Niterói24020-141, RJ, Brazil.
Rodolfo G FiorotDepartamento de Química Orgânica, Universidade Federal Fluminense, Campus do Valonguinho, Outeiro de São João Batista, s/n, Niterói24020-141, RJ, Brazil.
Flaviana R F DiasDepartamento de Química Orgânica, Universidade Federal Fluminense, Campus do Valonguinho, Outeiro de São João Batista, s/n, Niterói24020-141, RJ, Brazil.ORCID https://orcid.org/0000-0002-7069-9887
Vinícius R CamposDepartamento de Química Orgânica, Universidade Federal Fluminense, Campus do Valonguinho, Outeiro de São João Batista, s/n, Niterói24020-141, RJ, Brazil.
Vitor F FerreiraFaculdade de Farmácia, Departamento de Tecnologia Farmacêutica, Programa de Pós-Graduação em Química, Universidade Federal Fluminense, Outeiro de São João Batista, s/n, Niterói24241-000, RJ, Brazil.
Anna C CunhaDepartamento de Química Orgânica, Universidade Federal Fluminense, Campus do Valonguinho, Outeiro de São João Batista, s/n, Niterói24020-141, RJ, Brazil.
Wagner B De AlmeidaLaboratório de Química Computacional e Modelagem Molecular, Departamento de Química Inorgânica, Universidade Federal Fluminense, Campus do Valonguinho, Outeiro de São João Batista, s/n, Niterói24020-150, RJ, Brazil.ORCID https://orcid.org/0000-0003-0785-2284

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Two different products were obtained by the regiodivergent reaction of benzoquinone derivatives with phenolates and anilines: 3-aryloxybenzoquinone and 2-phenylamino-3-bromobenzoquinone. Calculated density functional theory free energies of reaction values corroborate the experimental observation of the formation of the substitution product in the reaction with phenolates in acetonitrile and the product of addition/oxidation for the reaction with aniline in water. Calculated charges and Fukui functions are similar for C2 and C3 atoms, indicating an equal possibility to suffer a nucleophilic attack. The calculated energy barriers for nucleophilic attack steps indicated that the first steps of the substitution with phenolates and addition/oxidation with anilines are faster, which justifies the formation of the respective products. The natural bond order analysis for the transition states revealed that there is a strong interaction between lone pairs of N and O atoms and the π

Identifiers

PMID36385806
PMCPMC9647872

What OpenQuestion holds

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LicenceCC BY-NC-ND
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Registered trials

None linked

Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.