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The Mechanism of Phosphonium Ylide Alcoholysis and Hydrolysis: Concerted Addition of the O−H Bond Across the P=C Bond

Overview of attention for article published in Chemistry - A European Journal, June 2016
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About this Attention Score

  • In the top 25% of all research outputs scored by Altmetric
  • High Attention Score compared to outputs of the same age (85th percentile)
  • High Attention Score compared to outputs of the same age and source (94th percentile)

Mentioned by

news
1 news outlet
twitter
3 tweeters

Citations

dimensions_citation
24 Dimensions

Readers on

mendeley
29 Mendeley
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Title
The Mechanism of Phosphonium Ylide Alcoholysis and Hydrolysis: Concerted Addition of the O−H Bond Across the P=C Bond
Published in
Chemistry - A European Journal, June 2016
DOI 10.1002/chem.201600530
Pubmed ID
Authors

Peter A. Byrne, Declan G. Gilheany

Abstract

The previous work on the hydrolysis and alcoholysis reactions of phosphonium ylides is summarized and reviewed in the context of their currently accepted mechanisms. Several experimental facts relating to ylide hydrolysis and to salt and ylide alcoholysis are shown to conflict with those mechanisms. In particular, we demonstrate that the pKa values of water and alcohols are too high in organic media to bring about protonation of ylide. Therefore, we propose concerted addition of the water or alcohol O-H bond across the ylide P=C bond. In support of this, we provide NMR spectroscopic evidence for equilibrium between ylide and aclohol that does not require the involvement of phosphonium hydroxide. We report the first P-alkoxyphosphorane to be characterised by NMR spectroscopy that does not undergo exchange on an NMR timescale. Two-dimensional NMR spectroscopic techniques have been applied to the characterisation to P-alkoxyphosphoranes for the first time.

Twitter Demographics

The data shown below were collected from the profiles of 3 tweeters who shared this research output. Click here to find out more about how the information was compiled.

Mendeley readers

The data shown below were compiled from readership statistics for 29 Mendeley readers of this research output. Click here to see the associated Mendeley record.

Geographical breakdown

Country Count As %
Unknown 29 100%

Demographic breakdown

Readers by professional status Count As %
Student > Ph. D. Student 9 31%
Researcher 7 24%
Student > Doctoral Student 3 10%
Student > Master 3 10%
Student > Bachelor 2 7%
Other 3 10%
Unknown 2 7%
Readers by discipline Count As %
Chemistry 21 72%
Materials Science 2 7%
Chemical Engineering 1 3%
Agricultural and Biological Sciences 1 3%
Engineering 1 3%
Other 0 0%
Unknown 3 10%

Attention Score in Context

This research output has an Altmetric Attention Score of 11. 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 29 September 2016.
All research outputs
#1,177,298
of 12,183,333 outputs
Outputs from Chemistry - A European Journal
#461
of 11,921 outputs
Outputs of similar age
#38,638
of 277,526 outputs
Outputs of similar age from Chemistry - A European Journal
#25
of 475 outputs
Altmetric has tracked 12,183,333 research outputs across all sources so far. Compared to these this one has done particularly well and is in the 90th percentile: it's in the top 10% of all research outputs ever tracked by Altmetric.
So far Altmetric has tracked 11,921 research outputs from this source. They receive a mean Attention Score of 3.3. This one has done particularly well, scoring higher than 96% 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 277,526 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 85% of its contemporaries.
We're also able to compare this research output to 475 others from the same source and published within six weeks on either side of this one. This one has done particularly well, scoring higher than 94% of its contemporaries.