Version 1
: Received: 26 February 2019 / Approved: 28 February 2019 / Online: 28 February 2019 (07:00:19 CET)
How to cite:
Ahn, S.; Kim, D.; Kim, E.; Lee, Y. Formation of Potassium 2-Hydroxy-6-naphthoate by Kolbe-Schmitt Carboxylation: A Joint Experimental and Theoretical Study. Preprints2019, 2019020262. https://doi.org/10.20944/preprints201902.0262.v1
Ahn, S.; Kim, D.; Kim, E.; Lee, Y. Formation of Potassium 2-Hydroxy-6-naphthoate by Kolbe-Schmitt Carboxylation: A Joint Experimental and Theoretical Study. Preprints 2019, 2019020262. https://doi.org/10.20944/preprints201902.0262.v1
Ahn, S.; Kim, D.; Kim, E.; Lee, Y. Formation of Potassium 2-Hydroxy-6-naphthoate by Kolbe-Schmitt Carboxylation: A Joint Experimental and Theoretical Study. Preprints2019, 2019020262. https://doi.org/10.20944/preprints201902.0262.v1
APA Style
Ahn, S., Kim, D., Kim, E., & Lee, Y. (2019). Formation of Potassium 2-Hydroxy-6-naphthoate by Kolbe-Schmitt Carboxylation: A Joint Experimental and Theoretical Study. Preprints. https://doi.org/10.20944/preprints201902.0262.v1
Chicago/Turabian Style
Ahn, S., Eung-Gun Kim and Yong-Kul Lee. 2019 "Formation of Potassium 2-Hydroxy-6-naphthoate by Kolbe-Schmitt Carboxylation: A Joint Experimental and Theoretical Study" Preprints. https://doi.org/10.20944/preprints201902.0262.v1
Abstract
The reaction mechanism of the carboxylation of K-2-naphthoxide was investigated by density functional theory calculations and spectroscopic studies. The reaction intermediates and products were confirmed by CO2 adsorbed-FTIR and 1H-NMR measurements. Four steps of the reaction pathway were identified: CO2 activation, electrophilic substitution, CO2-K complex rearrangement, and H-shift, producing 2-hydroxy-1-naphthoic acid (2,1-HNA), 2-hydroxy-3-naphthoic acid (2,3-HNA), and 2-hydroxy-6-naphthoic acid (2,6-HNA). The occurrence of CO2-K complex rearrangement was also confirmed. These energy profiles of reaction pathways for the reaction intermediates were well consistent the experimental results on the carboxylation of K-2-naphthoxide.
Keywords
2-Hydroxy-6-naphthoic acid; CO2 fixation; Carboxylation; DFT
Subject
Chemistry and Materials Science, Organic Chemistry
Copyright:
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
