Preprint Article Version 1 This version is not peer-reviewed

Formation of Potassium 2-Hydroxy-6-naphthoate by Kolbe-Schmitt Carboxylation: A Joint Experimental and Theoretical Study

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. Preprints 2019, 2019020262 (doi: 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 (doi: 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.

Subject Areas

2-Hydroxy-6-naphthoic acid; CO2 fixation; Carboxylation; DFT

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