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Stereoelectronic Effects Dictate Molecular Conformation and Biological Function of Heterocyclic Amides

Overview of attention for article published in Journal of the American Chemical Society, August 2014
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About this Attention Score

  • Good Attention Score compared to outputs of the same age (72nd percentile)
  • Above-average Attention Score compared to outputs of the same age and source (57th percentile)

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Citations

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61 Mendeley
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Title
Stereoelectronic Effects Dictate Molecular Conformation and Biological Function of Heterocyclic Amides
Published in
Journal of the American Chemical Society, August 2014
DOI 10.1021/ja506518t
Pubmed ID
Authors

Robert C. Reid, Mei-Kwan Yau, Ranee Singh, Junxian Lim, David P. Fairlie

Abstract

Heterocycles adjacent to amides can have important influences on molecular conformation due to stereoelectronic effects exerted by the heteroatom. This was shown for imidazole- and thiazole-amides by comparing low energy conformations (ab initio MP2 and DFT calculations), charge distribution, dipole moments, and known crystal structures which support a general principle. Switching a heteroatom from nitrogen to sulfur altered the amide conformation, producing different three-dimensional electrostatic surfaces. Differences were attributed to different dipole and orbital alignments and spectacularly translated into opposing agonist vs antagonist functions in modulating a G-protein coupled receptor for inflammatory protein complement C3a on human macrophages. Influences of the heteroatom were confirmed by locking the amide conformation using fused bicyclic rings. These findings show that stereoelectronic effects of heterocycles modulate molecular conformation and can impart strikingly different biological properties.

Mendeley readers

Mendeley readers

The data shown below were compiled from readership statistics for 61 Mendeley readers of this research output. Click here to see the associated Mendeley record.

Geographical breakdown

Country Count As %
Switzerland 1 2%
Unknown 60 98%

Demographic breakdown

Readers by professional status Count As %
Researcher 22 36%
Student > Ph. D. Student 10 16%
Student > Master 5 8%
Student > Bachelor 4 7%
Student > Doctoral Student 2 3%
Other 3 5%
Unknown 15 25%
Readers by discipline Count As %
Chemistry 35 57%
Pharmacology, Toxicology and Pharmaceutical Science 2 3%
Agricultural and Biological Sciences 2 3%
Medicine and Dentistry 2 3%
Immunology and Microbiology 1 2%
Other 2 3%
Unknown 17 28%
Attention Score in Context

Attention Score in Context

This research output has an Altmetric Attention Score of 4. This is our high-level measure of the quality and quantity of online attention that it has received. This Attention Score, as well as the ranking and number of research outputs shown below, was calculated when the research output was last mentioned on 02 July 2017.
All research outputs
#6,406,498
of 22,760,687 outputs
Outputs from Journal of the American Chemical Society
#25,886
of 61,917 outputs
Outputs of similar age
#61,395
of 231,138 outputs
Outputs of similar age from Journal of the American Chemical Society
#210
of 542 outputs
Altmetric has tracked 22,760,687 research outputs across all sources so far. This one has received more attention than most of these and is in the 70th percentile.
So far Altmetric has tracked 61,917 research outputs from this source. They typically receive a little more attention than average, with a mean Attention Score of 6.8. This one has gotten more attention than average, scoring higher than 56% of its peers.
Older research outputs will score higher simply because they've had more time to accumulate mentions. To account for age we can compare this Altmetric Attention Score to the 231,138 tracked outputs that were published within six weeks on either side of this one in any source. This one has gotten more attention than average, scoring higher than 72% of its contemporaries.
We're also able to compare this research output to 542 others from the same source and published within six weeks on either side of this one. This one has gotten more attention than average, scoring higher than 57% of its contemporaries.