Evidence map›Paper›PMID 27035057›Full record

ArticleThe Journal of organic chemistry2016

Lithium Enolates Derived from Pyroglutaminol: Aggregation, Solvation, and Atropisomerism.

Michael J Houghton, Naomi A Biok, Christopher J Huck, Russell F Algera, Ivan Keresztes, Stephen W Wright, David B Collum

Open access · greenAbstract read
In one paragraph

Article in The Journal of organic chemistry, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.

0numbers the graph read from it
0cells of the map it votes in
3citing papers in PubMed
0.5field-weighted citation impact, top 23% 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

3 citing papers in PubMed, 8 citations in OpenAlex.

  1. Molecular Dynamics Investigations of Dienolate [4 + 2] Reactions.Journal of the American Chemical Society · 2024
    Article
  2. Article
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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 at 2 institutions in 1 country.

Michael J HoughtonDepartment of Chemistry and Chemical Biology Baker Laboratory, Cornell University Ithaca , New York 14853-1301, United States.
Naomi A BiokDepartment of Chemistry and Chemical Biology Baker Laboratory, Cornell University Ithaca , New York 14853-1301, United States.
Christopher J HuckDepartment of Chemistry and Chemical Biology Baker Laboratory, Cornell University Ithaca , New York 14853-1301, United States.
Russell F AlgeraDepartment of Chemistry and Chemical Biology Baker Laboratory, Cornell University Ithaca , New York 14853-1301, United States.
Ivan KeresztesDepartment of Chemistry and Chemical Biology Baker Laboratory, Cornell University Ithaca , New York 14853-1301, United States.
Stephen W WrightWorldwide Medicinal Chemistry, Pfizer Global Research and Development , 445 Eastern Point Road, Groton, Connecticut 06340, United States.
David B CollumDepartment of Chemistry and Chemical Biology Baker Laboratory, Cornell University Ithaca , New York 14853-1301, United States.
Cornell University · USPfizer (United States) · US

Funding

Chemistry of Lithium EnolatesR01GM077167 · NIGMS · CORNELL UNIVERSITY · PI COLLUM, DAVID B. · 2006 to 2018
$4.1M
NIGMS NIH HHS R01 GM077167
6 · The paper itself

Abstract

Lithium enolates derived from protected pyroglutaminols were characterized by using (6)Li, (13)C, and (19)F NMR spectroscopies in conjunction with the method of continuous variations. Mixtures of tetrasolvated dimers and tetrasolvated tetramers in different proportions depend on the steric demands of the hemiaminal protecting group, tetrahydrofuran concentration, and the presence or absence of an α-fluoro moiety. The high steric demands of the substituted bicyclo[3.3.0] ring system promote dimers to an unusual extent and allow solvents and atropisomers in cubic tetramers to be observed in the slow-exchange limit. Pyridine used as a (6)Li chemical shift reagent proved useful in assigning solvation numbers.

Indexed as

Bridged Bicyclo CompoundsCarbon IsotopesFluorineIsotopesLithiumLithium CompoundsMagnetic Resonance SpectroscopyModels, MolecularMolecular StructurePyrrolesStereoisomerismBridged Bicyclo CompoundsCarbon IsotopesFluorineIsotopesLithiumLithium CompoundspyroglutaminolPyrroles

Identifiers

PMID27035057
PMCPMC5245164
OpenAlexW2313382146

What OpenQuestion holds

Textmetadata
LicenceTDM
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.