Substituent Effects and the Energetics of Noncatalyzed Aryl Halide Aminations: A Theoretical Investigation.

Supreeth Prasad, Dylan D Rodene, Michael B Burkholder, Kelling J Donald, B Frank Gupton

Abstract read

In one paragraph

Article in ACS omega, 2021. 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.

Deciphering the Reaction Cycle Mechanisms and Key Reaction Factors of Monochlorosilane by Disproportionation of Dichlorosilane via Experiments and Density Functional Theory.ACS omega · 2025
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

5 authors.

Supreeth PrasadDepartment of Chemistry, University of California-Davis, Davis, California 95616, United States.ORCID https://orcid.org/0000-0003-3496-4388

Dylan D RodeneDepartment of Chemical and Life Science Engineering, Virginia Commonwealth University, Richmond, Virginia 23284, United States.ORCID https://orcid.org/0000-0002-5235-4260

Michael B BurkholderDepartment of Chemical and Life Science Engineering, Virginia Commonwealth University, Richmond, Virginia 23284, United States.ORCID https://orcid.org/0000-0003-1506-0260

Kelling J DonaldDepartment of Chemistry, University of Richmond, Richmond, Virginia 23173, United States.ORCID https://orcid.org/0000-0001-9032-4225

B Frank GuptonDepartment of Chemical and Life Science Engineering, Virginia Commonwealth University, Richmond, Virginia 23284, United States.ORCID https://orcid.org/0000-0002-8165-1088

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

We report the influence of substituents and physical conditions on activation energies for the noncatalyzed amination (C-N cross-coupling reactions) of aryl halides. We uncover a significant correlation between the barrier heights of the C-N bond formation and Hammett σ parameters-a formal measure of the electron-withdrawing or -donating ability of substituents on the aryl halides. Our results indicate that such correlations are useful predictive tools for the amination of aryl halides over a wide range of substituent types. From 54 cases studied (six substituents occupying specific positions relative to halogen atoms), the 2-COOHPhI + NH

Identifiers

PMID34693141

DOI10.1021/acsomega.1c03934

PMCPMC8529657

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LicenceCC BY-NC-ND

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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.