ArticleJournal of the American Chemical Society2017
Experimental and Computational Gas Phase Acidities of Conjugate Acids of Triazolylidene Carbenes: Rationalizing Subtle Electronic Effects.
Article in Journal of the American Chemical Society, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- OSCAR: an extensive repository of chemically and functionally diverse organocatalysts.Chemical science · 2022Article
- Substituent Effects on the Basicity of Patriscabrin A and Lettucenin A: Evolution Favors the Aromatic?ACS omega · 2021Article
- Halogen-containing heteroaromatic carbenes of the 1,2,4-triazole series and their transformations.RSC advances · 2021Article
- Unravelling mechanistic features of organocatalysis with in situ modifications at the secondary sphere.Nature chemistry · 2019Article
- COFrontiers in chemistry · 2018Article
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Authors and funding
7 authors.
Funding
Abstract
In recent years, triazolylidene carbenes have come to the forefront as important organocatalysts for a wide range of reactions. The fundamental properties of these species, however, remain largely unknown. Herein, the gas phase acidities have been measured and calculated for a series of triazolium cations (the conjugate acids of the triazolylidene carbenes) that have not been heretofore examined in vacuo. The results are discussed in the context of these species as catalysts. We find correlations between the gas phase acidity and selectivity in two Umpolung reactions catalyzed by these species; such correlations are the first of their kind. We are able to use these linear correlations to improve reaction enantioselectivity. These results establish the possibility of using these thermochemical properties to predict reactivity in related transformations.
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