Evidence map›Paper›PMID 27409515›Full record

ArticleOrganic letters2016

n→π* Interactions Are Competitive with Hydrogen Bonds.

Robert W Newberry, Samuel J Orke, Ronald T Raines

Abstract read
In one paragraph

Article in Organic letters, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.

0numbers the graph read from it
0cells of the map it votes in
8citing 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

8 citing papers in PubMed.

  1. Article
  2. Article
  3. Article
  4. Review
  5. Secondary Forces in Protein Folding.ACS chemical biology · 2019
    Review
  6. Article
  7. The n→π* Interaction.Accounts of chemical research · 2017
    Article
  8. 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

3 authors.

Robert W NewberryDepartment of Chemistry and ‡Department of Biochemistry, University of Wisconsin-Madison , Madison, Wisconsin 53706, United States.
Samuel J OrkeDepartment of Chemistry and ‡Department of Biochemistry, University of Wisconsin-Madison , Madison, Wisconsin 53706, United States.
Ronald T RainesDepartment of Chemistry and ‡Department of Biochemistry, University of Wisconsin-Madison , Madison, Wisconsin 53706, United States.

Funding

BIOTECHNOLOGY TRAINING PROGRAMT32GM008349 · NIGMS · UNIVERSITY OF WISCONSIN-MADISON · PI FOX, BRIAN G · 1989 to 2019
$22.5M
TR&D 3: TECHNOLOGY DEVELOPMENT FOR NMR STUDIES OF SMALL MOLECULES (METABOLOMICS, NATURAL PRODUCTS, METABOLITE-PROTEIN INTERACTIONS) pp.537-585 P41GM103399 · NIGMS · UNIVERSITY OF WISCONSIN-MADISON · PI MARKLEY, JOHN LUTE · 2012 to 2019
$9.4M
COLLAGEN STRUCTURE AND STABILITY IN VITRO AND IN VIVOR01AR044276 · NIAMS · UNIVERSITY OF WISCONSIN-MADISON · PI RAINES, RONALD T · 1996 to 2017
$5.6M
NIAMS NIH HHS R01 AR044276NIGMS NIH HHS P41 GM103399NIGMS NIH HHS T32 GM008349
6 · The paper itself

Abstract

Because carbonyl groups can participate in both hydrogen bonds and n→π* interactions, these two interactions likely affect one another. Herein, enhancement of an amidic n→π* interaction is shown to reduce the ability of β-keto amides to tautomerize to the enol, indicating decreased hydrogen-bonding capacity of the amide carbonyl group. Thus, an n→π* interaction can have a significant effect on the strength of a hydrogen bond to the same carbonyl group.

Indexed as

AmidesHydrogen BondingKetonesMolecular ConformationAmidesKetones

Identifiers

PMID27409515
PMCPMC5089869

What OpenQuestion holds

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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.