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Chloroform as a Hydrogen Atom Donor in Barton Reductive Decarboxylation Reactions

Overview of attention for article published in Journal of Organic Chemistry, June 2013
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Title
Chloroform as a Hydrogen Atom Donor in Barton Reductive Decarboxylation Reactions
Published in
Journal of Organic Chemistry, June 2013
DOI 10.1021/jo400927y
Pubmed ID
Authors

Junming Ho, Jingjing Zheng, Rubén Meana-Pañeda, Donald G. Truhlar, Eun Jung Ko, G. Paul Savage, Craig M. Williams, Michelle L. Coote, John Tsanaktsidis

Abstract

The utility of chloroform as both a solvent and a hydrogen atom donor in Barton reductive decarboxylation of a range of carboxylic acids was recently demonstrated (Ko, E. J. et al. Org. Lett. 2011, 13, 1944). In the present work, a combination of electronic structure calculations, direct dynamics calculations, and experimental studies was carried out to investigate how chloroform acts as a hydrogen atom donor in Barton reductive decarboxylations and to determine the scope of this process. The results from this study show that hydrogen atom transfer from chloroform occurs directly under kinetic control and is aided by a combination of polar effects and quantum mechanical tunneling. Chloroform acts as an effective hydrogen atom donor for primary, secondary, and tertiary alkyl radicals, although significant chlorination was also observed with unstrained tertiary carboxylic acids.

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Mendeley readers

Mendeley readers

The data shown below were compiled from readership statistics for 49 Mendeley readers of this research output. Click here to see the associated Mendeley record.

Geographical breakdown

Country Count As %
Denmark 1 2%
Unknown 48 98%

Demographic breakdown

Readers by professional status Count As %
Student > Ph. D. Student 10 20%
Researcher 5 10%
Student > Bachelor 4 8%
Other 4 8%
Student > Doctoral Student 3 6%
Other 9 18%
Unknown 14 29%
Readers by discipline Count As %
Chemistry 29 59%
Biochemistry, Genetics and Molecular Biology 2 4%
Unspecified 2 4%
Computer Science 2 4%
Sports and Recreations 1 2%
Other 0 0%
Unknown 13 27%
Attention Score in Context

Attention Score in Context

This research output has an Altmetric Attention Score of 3. 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 14 October 2017.
All research outputs
#8,535,684
of 25,377,790 outputs
Outputs from Journal of Organic Chemistry
#10,592
of 28,613 outputs
Outputs of similar age
#71,386
of 209,143 outputs
Outputs of similar age from Journal of Organic Chemistry
#44
of 135 outputs
Altmetric has tracked 25,377,790 research outputs across all sources so far. This one is in the 43rd percentile – i.e., 43% of other outputs scored the same or lower than it.
So far Altmetric has tracked 28,613 research outputs from this source. They receive a mean Attention Score of 4.5. This one is in the 15th percentile – i.e., 15% of its peers scored the same or lower than it.
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 209,143 tracked outputs that were published within six weeks on either side of this one in any source. This one is in the 48th percentile – i.e., 48% of its contemporaries scored the same or lower than it.
We're also able to compare this research output to 135 others from the same source and published within six weeks on either side of this one. This one is in the 49th percentile – i.e., 49% of its contemporaries scored the same or lower than it.