Photochemical Kinetics of Pyruvic Acid in Aqueous Solution

Harris, Allison E. Reed; Ervens, B.; Shoemaker, Richard K.; Kroll, Jay A.; Rapf, Rebecca J.; Griffith, Elizabeth C.; Monod, Anne; Vaida, Veronica

doi:10.1021/jp502186q

Cited by 84 publications

(277 citation statements)

References 92 publications

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“…This is a slight blue shift from that of pyruvic acid (λ max ≈ 320 nm), 28,67 but there is not a significant change in the absorption maximum as a function of changing alkyl tail length as for the four oxoacids investigated here (spectra shown in Figure S1). …”

Section: Methodsmentioning

confidence: 67%

“…17–25 The surface-active molecules found in the SML are often biological in origin, 14,26,27 but abiotic photochemical sources may be additional, important contributors. 11,12,23,28–30 Such sunlight-driven reactions are critical in the understanding of the formation of marine-derived primary organic aerosol and SOA, 31–37 influencing visibility, human health, cloud formation, and radiative forcing. 17,19,38–46 …”

Section: Introductionmentioning

confidence: 99%

“…Previously, the photochemistry of the simplest of α-keto acid, pyruvic acid, has been studied in detail in both the gas 53–60 and the aqueous phases, 28,61–69 due to its atmospheric rele-vance. 48,70–78 Like all α-keto acids, pyruvic acid absorbs light in the near-UV within the spectral range of wavelengths of sunlight that are available near the surface of the Earth, and direct photolysis is its main atmospheric sink.…”

Section: Introductionmentioning

confidence: 99%

“…68 These covalently bonded dimers and trimers 80 are generated in relatively high yields from the recombination of photochemically generated organic radicals and are the major observed photoproducts, especially under oxygen-limited reaction conditions. 28,63,64,67 …”

Section: Introductionmentioning

confidence: 99%

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Photochemical Synthesis of Oligomeric Amphiphiles from Alkyl Oxoacids in Aqueous Environments

Rapf¹,

Perkins²,

Yang³

et al. 2017

J. Am. Chem. Soc.

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The aqueous phase photochemistry of a series of amphiphilic α-keto acids with differing linear alkyl chain lengths was investigated, demonstrating the ability of sunlight-initiated reactions to build molecular complexity under environmentally relevant conditions. We show that the photochemical reaction mechanisms for α-keto acids in aqueous solution are robust and generalizable across alkyl chain lengths. The organic radicals generated during photolysis are indiscriminate, leading to a large mixture of photoproducts that are observed using high-resolution electrospray ionization mass spectrometry, but these products are identifiable following literature photochemical mechanisms. The alkyl oxoacids under study here can undergo a Norrish Type II reaction to generate pyruvic acid, increasing the diversity of observed photoproducts. The major products of this photochemistry are covalently bonded dimers and trimers of the starting oxoacids, many of which are multitailed lipids. The properties of these oligomers are discussed, including their spontaneous self-assembly into aggregates.

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Section: Methodsmentioning

confidence: 67%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Photochemical Synthesis of Oligomeric Amphiphiles from Alkyl Oxoacids in Aqueous Environments

Rapf¹,

Perkins²,

Yang³

et al. 2017

J. Am. Chem. Soc.

Self Cite

View full text Add to dashboard Cite

show abstract

“…Figure 1c illustrates the photochemical and polymerization mechanism resulting in the production of the dimer or trimer molecule, as well as radicals. 3-PPA first absorbs light through its carbonyl chromophore, resulting in the production of radicals, analogous to the wellknown photochemistry of pyruvic acid [17,19,20]. 3-PPA is reversibly hydrated in aqueous solution.…”

Section: Resultsmentioning

confidence: 99%

Photo-induced synthesis glucose-responsive carriers for controlled release of insulin in vitro

Jiang

Li³

et al. 2015

Colloid Polym Sci

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The glucose-responsive amphiphilic poly(PEGMAco-AAPBA) copolymer micelles as drug carriers have been developed using 3-phenylpyruvic acid (3-PPA) as photoinitiator. Under the light irradiation, 3-PPA could be self-polymerized into the trimer structure to execute the emulsifier and initiator functions that confirmed by gas chromatography-mass spectrum (GC-MS) analysis. The structure and morphology of resultant poly(PEGMA-co-AAPBA) micelles were characterized by 1 H NMR and TEM. Insulin, as the model drug of diabetes, was loaded into micelles during the photopolymerization process. The as-prepared polymeric micelles exhibited the excellent glucose sensitivity. The loaded insulin could be released from micelles triggered by regulation of temperature and glucose concentration in the environment. The new drug carriers provided a potential application for the therapy of diabetes based on glucose-sensitive controlled drug delivery systems.

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Recent advances in understanding secondary organic aerosol: Implications for global climate forcing

Shrivastava

Cappa

Fan

et al. 2017

Reviews of Geophysics

646

668

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Anthropogenic emissions and land use changes have modified atmospheric aerosol concentrations and size distributions over time. Understanding preindustrial conditions and changes in organic aerosol due to anthropogenic activities is important because these features (1) influence estimates of aerosol radiative forcing and (2) can confound estimates of the historical response of climate to increases in greenhouse gases. Secondary organic aerosol (SOA), formed in the atmosphere by oxidation of organic gases, represents a major fraction of global submicron‐sized atmospheric organic aerosol. Over the past decade, significant advances in understanding SOA properties and formation mechanisms have occurred through measurements, yet current climate models typically do not comprehensively include all important processes. This review summarizes some of the important developments during the past decade in understanding SOA formation. We highlight the importance of some processes that influence the growth of SOA particles to sizes relevant for clouds and radiative forcing, including formation of extremely low volatility organics in the gas phase, acid‐catalyzed multiphase chemistry of isoprene epoxydiols, particle‐phase oligomerization, and physical properties such as volatility and viscosity. Several SOA processes highlighted in this review are complex and interdependent and have nonlinear effects on the properties, formation, and evolution of SOA. Current global models neglect this complexity and nonlinearity and thus are less likely to accurately predict the climate forcing of SOA and project future climate sensitivity to greenhouse gases. Efforts are also needed to rank the most influential processes and nonlinear process‐related interactions, so that these processes can be accurately represented in atmospheric chemistry‐climate models.

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Photochemical Kinetics of Pyruvic Acid in Aqueous Solution

Cited by 84 publications

References 92 publications

Photochemical Synthesis of Oligomeric Amphiphiles from Alkyl Oxoacids in Aqueous Environments

Photochemical Synthesis of Oligomeric Amphiphiles from Alkyl Oxoacids in Aqueous Environments

Photo-induced synthesis glucose-responsive carriers for controlled release of insulin in vitro

Recent advances in understanding secondary organic aerosol: Implications for global climate forcing

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