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pKa Scale for Cyclopropenium Ions with Applications in CO2 Capture.

Publication ,  Journal Article
Vemulapalli, S; Guest, M; Smajlagic, I; Dudding, T
Published in: J Org Chem
September 3, 2021

Molecular acid-base properties are core to understanding chemical systems and the prediction of reactivity. This axiom holds for cyclopropenium ions in terms of their broad use as (organo)catalysts, ligands, redox-flow batteries, and applications in materials sciences. In view of this significant status, and with it, the critical importance of acidity, we disclose in this report the first comprehensive computational study of the pKa values of cyclopropenium ions employing a subset of 70 structurally diverse cyclopropenium derivatives, density functional computations, and Hammett linear free-energy relationships. Capitalizing upon these computed findings, and with an eye toward greenhouse gas trapping, we further document the timely use of a cyclopropenium-cyclopropenylidene coupled platform for CO2 capture and light-triggered release.

Duke Scholars

Published In

J Org Chem

DOI

EISSN

1520-6904

Publication Date

September 3, 2021

Volume

86

Issue

17

Start / End Page

11835 / 11844

Location

United States

Related Subject Headings

  • Organic Chemistry
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry
 

Citation

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Vemulapalli, S., Guest, M., Smajlagic, I., & Dudding, T. (2021). pKa Scale for Cyclopropenium Ions with Applications in CO2 Capture. J Org Chem, 86(17), 11835–11844. https://doi.org/10.1021/acs.joc.1c01255
Vemulapalli, Srini, Matt Guest, Ivor Smajlagic, and Travis Dudding. “pKa Scale for Cyclopropenium Ions with Applications in CO2 Capture.J Org Chem 86, no. 17 (September 3, 2021): 11835–44. https://doi.org/10.1021/acs.joc.1c01255.
Vemulapalli S, Guest M, Smajlagic I, Dudding T. pKa Scale for Cyclopropenium Ions with Applications in CO2 Capture. J Org Chem. 2021 Sep 3;86(17):11835–44.
Vemulapalli, Srini, et al. “pKa Scale for Cyclopropenium Ions with Applications in CO2 Capture.J Org Chem, vol. 86, no. 17, Sept. 2021, pp. 11835–44. Pubmed, doi:10.1021/acs.joc.1c01255.
Vemulapalli S, Guest M, Smajlagic I, Dudding T. pKa Scale for Cyclopropenium Ions with Applications in CO2 Capture. J Org Chem. 2021 Sep 3;86(17):11835–11844.
Journal cover image

Published In

J Org Chem

DOI

EISSN

1520-6904

Publication Date

September 3, 2021

Volume

86

Issue

17

Start / End Page

11835 / 11844

Location

United States

Related Subject Headings

  • Organic Chemistry
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry