Enhanced Acidity of Acetic and Pyruvic Acids on the Surface of Water

Alexis J. Eugene; Elizabeth A. Pillar-Little; Agustín J. Colussi; Marcelo I. Guzman

doi:10.1021/acs.langmuir.8b01606

Enhanced Acidity of Acetic and Pyruvic Acids on the Surface of Water

Alexis J. Eugene, Elizabeth A. Pillar-Little, Agustín J. Colussi, Marcelo I. Guzman

Research output: Contribution to journal › Article › peer-review

39 Scopus citations

Abstract

Understanding the acid-base behavior of carboxylic acids on aqueous interfaces is a fundamental issue in nature. Surface processes involving carboxylic acids such as acetic and pyruvic acids play roles in (1) the transport of nutrients through cell membranes, (2) the cycling of metabolites relevant to the origin of life, and (3) the photooxidative processing of biogenic and anthropogenic emissions in aerosols and atmospheric waters. Here, we report that 50% of gaseous acetic acid and pyruvic acid molecules transfer a proton to the surface of water at pH 2.8 and 1.8 units lower than their respective acidity constants pK_a = 4.6 and 2.4 in bulk water. These findings provide key insights into the relative Bronsted acidities of common carboxylic acids versus interfacial water. In addition, the work estimates the reactive uptake coefficient of gaseous pyruvic acid by water to be γ_PA = 0.06. This work is useful to interpret the interfacial behavior of pyruvic acid under low water activity conditions, typically found in haze aerosols, clouds, and fog waters.

Original language	English
Pages (from-to)	9307-9313
Number of pages	7
Journal	Langmuir
Volume	34
Issue number	31
DOIs	https://doi.org/10.1021/acs.langmuir.8b01606
State	Published - Aug 7 2018

Bibliographical note

Funding Information:
M.I.G. thanks research funding from the National Science foundation under NSF CAREER award CHE-1255290. A.J.E. acknowledges the support by the NASA Earth and Space Science Fellowship (NESSF) Program. A.J.C. acknowledges funding from the National Science Foundation under grant AGS-1744353.

Publisher Copyright:
© 2018 American Chemical Society.

ASJC Scopus subject areas

Materials Science (all)
Condensed Matter Physics
Surfaces and Interfaces
Spectroscopy
Electrochemistry

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title = "Enhanced Acidity of Acetic and Pyruvic Acids on the Surface of Water",

abstract = "Understanding the acid-base behavior of carboxylic acids on aqueous interfaces is a fundamental issue in nature. Surface processes involving carboxylic acids such as acetic and pyruvic acids play roles in (1) the transport of nutrients through cell membranes, (2) the cycling of metabolites relevant to the origin of life, and (3) the photooxidative processing of biogenic and anthropogenic emissions in aerosols and atmospheric waters. Here, we report that 50% of gaseous acetic acid and pyruvic acid molecules transfer a proton to the surface of water at pH 2.8 and 1.8 units lower than their respective acidity constants pKa = 4.6 and 2.4 in bulk water. These findings provide key insights into the relative Bronsted acidities of common carboxylic acids versus interfacial water. In addition, the work estimates the reactive uptake coefficient of gaseous pyruvic acid by water to be γPA = 0.06. This work is useful to interpret the interfacial behavior of pyruvic acid under low water activity conditions, typically found in haze aerosols, clouds, and fog waters.",

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note = "Funding Information: M.I.G. thanks research funding from the National Science foundation under NSF CAREER award CHE-1255290. A.J.E. acknowledges the support by the NASA Earth and Space Science Fellowship (NESSF) Program. A.J.C. acknowledges funding from the National Science Foundation under grant AGS-1744353. Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

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Enhanced Acidity of Acetic and Pyruvic Acids on the Surface of Water

Abstract

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