Carboxylic acid catalyzed hydration of acetaldehyde

The Journal of Physical Chemistry. a
Heather A RypkemaJoseph S Francisco

Abstract

Electronic structure calculations of the pertinent stationary points on the potential energy surface show that carboxylic acids can act effectively as catalysts in the hydration of acetaldehyde. Barriers to this catalyzed process correlate strongly with the pKa of the acid, providing the potential to provide the predictive capacity of the effectiveness of carboxylic acid catalysts. Transition states for the acid-catalyzed systems take the form of pseudo-six-membered rings through the linear nature of their hydrogen bonds, which accounts for their relative stability compared to the more strained direct and water-catalyzed systems. When considered as a stepwise reaction of a dimerization followed by reaction/complexation, it is likely that collisional stabilization of the prereactive complex is more likely than reaction in the free gas phase, although the catalyzed hydration does retain the potential to proceed on water surfaces or in droplets. Lastly, it is observed that postreactive diol-acid complexes are significantly stable (∼12-17 kcal/mol) relative to isolated products, suggesting the possibility of long-lived hygroscopic species that could act as a seed molecule for condensation of secondary organic aerosols.

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Citations

Oct 10, 2015·Environmental Science & Technology·Jingjing LiuJing-Yao Liu
Apr 14, 2016·Accounts of Chemical Research·Manoj KumarJoseph S Francisco
Jan 11, 2017·The Journal of Physical Chemistry. a·Josue E PerezAmitabha Sinha
Nov 7, 2019·Physical Chemistry Chemical Physics : PCCP·Sourav GhoshalPranab Sarkar
Mar 3, 2018·Physical Chemistry Chemical Physics : PCCP·Xing-Feng TanEllen Mitchell
Dec 14, 2017·Physical Chemistry Chemical Physics : PCCP·Xiangli ShiWenxing Wang
Jan 28, 2021·The Journal of Organic Chemistry·Kaveh FarshadfarAlireza Ariafard
Jan 1, 2020·ACS Omega·Jeremy KuaHelen Loli
Mar 24, 2021·The Journal of Physical Chemistry. a·Rui WangTianlei Zhang
Jul 1, 2021·The Journal of Physical Chemistry. a·Parandaman ArathalaAmitabha Sinha
Nov 15, 2018·The Journal of Physical Chemistry. a·Arathala ParandamanAmitabha Sinha
Jan 25, 2018·The Journal of Physical Chemistry. a·Viivi HirvonenJonas Elm
Jun 30, 2018·The Journal of Physical Chemistry. a·Arathala ParandamanAmitabha Sinha

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