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Metal–Organic Frameworks Invert Molecular Reactivity: Lewis Acidic Phosphonium Zwitterions Catalyze the Aldol-Tishchenko Reaction

Overview of attention for article published in Journal of the American Chemical Society, December 2017
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About this Attention Score

  • In the top 25% of all research outputs scored by Altmetric
  • Good Attention Score compared to outputs of the same age (77th percentile)
  • Good Attention Score compared to outputs of the same age and source (65th percentile)

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6 X users
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1 patent

Citations

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29 Dimensions

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57 Mendeley
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Title
Metal–Organic Frameworks Invert Molecular Reactivity: Lewis Acidic Phosphonium Zwitterions Catalyze the Aldol-Tishchenko Reaction
Published in
Journal of the American Chemical Society, December 2017
DOI 10.1021/jacs.7b10928
Pubmed ID
Authors

Gerald Bauer, Daniele Ongari, Xiaoying Xu, Davide Tiana, Berend Smit, Marco Ranocchiari

Abstract

The influence of metal-organic frameworks (MOFs) as additives is herein described for the reaction of n-alkyl aldehydes in the presence of methylvinylketone and tri-phenylphosphine. In the absence of a MOF, the expected Morita-Baylis-Hillman product - a β-hydroxy enone - is observed. In the presence of MOFs with UMCM-1 and MOF-5 topologies, the reaction is selective to Aldol-Tishchenko products - the 1 and 3 n-alkylesters of 2-alkyl-1,3-diols - that is unprecedented in organocatalysis. The (3-oxo-2-butenyl)triphenylphosphonium zwitterion, a commonly known nucleophile, is identified as the catalytic active species. This zwitterion favours nucleophilic character in solution, whereas once confined within the framework, it becomes an electrophile yielding Aldol-Tishchenko selectivity. Computational investigations reveal a structural change in the phosphonium moiety induced by the steric confinement of the framework that makes it accessible and an electrophile.

X Demographics

X Demographics

The data shown below were collected from the profiles of 6 X users who shared this research output. Click here to find out more about how the information was compiled.
Mendeley readers

Mendeley readers

The data shown below were compiled from readership statistics for 57 Mendeley readers of this research output. Click here to see the associated Mendeley record.

Geographical breakdown

Country Count As %
Switzerland 1 2%
Unknown 56 98%

Demographic breakdown

Readers by professional status Count As %
Student > Ph. D. Student 12 21%
Researcher 6 11%
Student > Bachelor 6 11%
Student > Master 5 9%
Student > Doctoral Student 4 7%
Other 12 21%
Unknown 12 21%
Readers by discipline Count As %
Chemistry 29 51%
Chemical Engineering 4 7%
Physics and Astronomy 3 5%
Engineering 2 4%
Biochemistry, Genetics and Molecular Biology 1 2%
Other 3 5%
Unknown 15 26%
Attention Score in Context

Attention Score in Context

This research output has an Altmetric Attention Score of 7. 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 21 February 2023.
All research outputs
#4,729,450
of 23,394,907 outputs
Outputs from Journal of the American Chemical Society
#16,428
of 62,910 outputs
Outputs of similar age
#100,395
of 441,780 outputs
Outputs of similar age from Journal of the American Chemical Society
#186
of 543 outputs
Altmetric has tracked 23,394,907 research outputs across all sources so far. Compared to these this one has done well and is in the 79th percentile: it's in the top 25% of all research outputs ever tracked by Altmetric.
So far Altmetric has tracked 62,910 research outputs from this source. They typically receive a little more attention than average, with a mean Attention Score of 6.9. This one has gotten more attention than average, scoring higher than 73% 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 441,780 tracked outputs that were published within six weeks on either side of this one in any source. This one has done well, scoring higher than 77% of its contemporaries.
We're also able to compare this research output to 543 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 65% of its contemporaries.