Evidence map›Paper›PMID 37535477›Full record

ArticleThe Journal of organic chemistry2023

Experimental and Theoretical Exploration of the Kinetics and Thermodynamics of the Nucleophile-Induced Fragmentation of Ylidenenorbornadiene Carboxylates.

Abigail D Richardson, Scott J L'Heureux, Ava M Henry, Elizabeth A McDonough, Cameron J Fleischer, Cameron C McMullen, Trevor R Reynafarje, Gisele P Guerrero, Quinn E Williams, Qingyang Zhou and 10 more

Open access · hybridAbstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in The Journal of organic chemistry, 2023. 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
0.4field-weighted citation impact, top 42% of its field
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, 3 citations in OpenAlex.

  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

20 authors at 2 institutions in 1 country.

Abigail D RichardsonDepartment of Chemistry and Biochemistry, California Polytechnic State University, San Luis Obispo, California 93407, United States.ORCID 0000-0001-5900-5357
Scott J L'HeureuxDepartment of Chemistry and Biochemistry, California Polytechnic State University, San Luis Obispo, California 93407, United States.ORCID 0000-0002-2299-2253
Ava M HenryDepartment of Chemistry and Biochemistry, California Polytechnic State University, San Luis Obispo, California 93407, United States.
Elizabeth A McDonoughDepartment of Chemistry and Biochemistry, California Polytechnic State University, San Luis Obispo, California 93407, United States.
Cameron J FleischerDepartment of Chemistry and Biochemistry, California Polytechnic State University, San Luis Obispo, California 93407, United States.
Cameron C McMullenDepartment of Chemistry and Biochemistry, California Polytechnic State University, San Luis Obispo, California 93407, United States.
Trevor R ReynafarjeDepartment of Chemistry and Biochemistry, California Polytechnic State University, San Luis Obispo, California 93407, United States.
Gisele P GuerreroDepartment of Chemistry and Biochemistry, California Polytechnic State University, San Luis Obispo, California 93407, United States.
Quinn E WilliamsDepartment of Chemistry and Biochemistry, California Polytechnic State University, San Luis Obispo, California 93407, United States.
Qingyang ZhouDepartment of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095, United States.
David M MaloufDepartment of Chemistry and Biochemistry, California Polytechnic State University, San Luis Obispo, California 93407, United States.
Spencer E ThurmanDepartment of Chemistry and Biochemistry, California Polytechnic State University, San Luis Obispo, California 93407, United States.
Julia E SoellerDepartment of Chemistry and Biochemistry, California Polytechnic State University, San Luis Obispo, California 93407, United States.
Jerry Y ShengDepartment of Chemistry and Biochemistry, California Polytechnic State University, San Luis Obispo, California 93407, United States.
Erica A MedhurstDepartment of Chemistry and Biochemistry, California Polytechnic State University, San Luis Obispo, California 93407, United States.
Angel E CanalesDepartment of Chemistry and Biochemistry, California Polytechnic State University, San Luis Obispo, California 93407, United States.
Ty B CecilDepartment of Chemistry and Biochemistry, California Polytechnic State University, San Luis Obispo, California 93407, United States.
K N HoukDepartment of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095, United States.
Philip J CostanzoDepartment of Chemistry and Biochemistry, California Polytechnic State University, San Luis Obispo, California 93407, United States.
Daniel A BercoviciDepartment of Chemistry and Biochemistry, California Polytechnic State University, San Luis Obispo, California 93407, United States.ORCID 0000-0002-8502-9560
California Polytechnic State University · USUniversity of California, Los Angeles · US

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Ylidenenorbornadienes (YNDs), prepared by [4 + 2] cycloadditions between fulvenes and acetylene carboxylates, react with thiol nucleophiles to yield mixtures of four to eight diastereomers depending on the symmetry of the YND substrate. The mixtures of diastereomers fragment via a retro-[4 + 2] cycloaddition with a large variation in rate, with half-lives ranging from 16 to 11,000 min at 80 °C. The diastereomer-enriched samples of propane thiol adducts [YND-propanethiol (PTs)] were isolated and identified by nuclear Overhauser effect spectroscopy (NOESY) correlations. Simulated kinetics were used to extrapolate the rate constants of individual diastereomers from the observed rate data, and it correlated well with rate constants measured directly and from isolated diastereomer-enriched samples. The individual diastereomers of a model system fragment at differing rates with half-lives ranging from 5 to 44 min in CDCl

Identifiers

PMID37535477
PMCPMC10442913
OpenAlexW4385532447

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.