Oxidation of [3]naphthylenes to cations and dications converts local paratropicity into global diatropicity.

Abel Cárdenas, Zexin Jin, Yong Ni, Jishan Wu, Yan Xia, Francisco Javier Ramírez, Juan Casado

Abstract read

In one paragraph

Article in Beilstein journal of organic chemistry, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

0numbers the graph read from it

0cells of the map it votes in

0citing 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

0 citing papers in PubMed.

No citing paper in PubMed yet.

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

7 authors.

Abel CárdenasDepartment of Physical Chemistry, University of Málaga, Andalucia-Tech, Campus de Teatinos s/n, 29071 Málaga, Spain.ORCID https://orcid.org/0000-0002-0631-0160

Zexin JinDepartment of Chemistry, Stanford University, Stanford, CA 94305, USA.

Yong NiDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, Singapore.

Jishan WuDepartment of Chemistry, Stanford University, Stanford, CA 94305, USA.

Yan XiaDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, Singapore.

Francisco Javier RamírezDepartment of Physical Chemistry, University of Málaga, Andalucia-Tech, Campus de Teatinos s/n, 29071 Málaga, Spain.

Juan CasadoDepartment of Physical Chemistry, University of Málaga, Andalucia-Tech, Campus de Teatinos s/n, 29071 Málaga, Spain.ORCID https://orcid.org/0000-0003-0373-1303

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Oxidized states of polycyclic aromatic hydrocarbons are of importance as they represent charged conductive species in organic semiconductor substrates. In this work, we investigated the properties of radical cations and dications of linear and angular [3]naphthylenes, consisting of fused aromatic naphthalenoid and antiaromatic cyclobutadienoid moieties and containing different degrees of paratropicity. Electronic absorption and vibrational Raman spectroscopies were used to describe the more relevant bonding changes. Stretching force constants were evaluated to monitor the aromatic-antiaromatic alternation pattern upon oxidation. They showed us that the dication of linear [3]naphthylene became an overall global π-electron delocalized molecule. This result was supported by nucleus independent chemical shift (NICS) calculations and anisotropy of the current induced density (ACID) plots, as they evidenced the presence of a perimetral diatropic global ring current upon oxidation.

Indexed as

ACIDaromaticityforce constantsNICSspectroscopy

Identifiers

PMID39931685

DOI10.3762/bjoc.21.20

PMCPMC11809581

What OpenQuestion holds

Textmetadata

LicenceCC BY

Read underepoch 390

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.