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1. Complex Structures Resulting from Carboxylic Acid Self-Assembly: Comparison of 2-Naphthoic Acid to Quinaldic Acid and 3-Quinoline Carboxylic Acid

   https://doi.org/10.1021/acs.jpcc.9b01817  

   Petersen, Jacob P.; Brown, Ryan D.; Silski, Angela M.; Corcelli, Steven A.; Kandel, S. Alex (May 2019, The Journal of Physical Chemistry C)
2. Acid-Triggered, Acid-Generating, and Self-Amplifying Degradable Polymers

   https://doi.org/10.1021/jacs.8b07705  

   Miller, Kali A.; Morado, Ephraim G.; Samanta, Shampa R.; Walker, Brittany A.; Nelson, Arif Z.; Sen, Samya; Tran, Dung T.; Whitaker, Daniel J.; Ewoldt, Randy H.; Braun, Paul V.; et al (February 2019, Journal of the American Chemical Society)
3. Vapor-phase conversion of aqueous 3-hydroxybutyric acid and crotonic acid to propylene over solid acid catalysts

   https://doi.org/10.1039/d1cy01152a  

   Leow, Shijie; Koehler, Andrew J.; Cronmiller, Lauren E.; Huo, Xiangchen; Lahti, Gabriella D.; Li, Yalin; Hafenstine, Glenn R.; Vardon, Derek R.; Strathmann, Timothy J. (October 2021, Catalysis Science & Technology)

   Diverse sources of wastewater organic carbon can be microbially funneled into biopolymers like polyhydroxybutyrate (PHB) that can be further valorized by conversion to hydrocarbon fuels and industrial chemicals. We report the vapor-phase dehydration and decarboxylation of PHB-derived monomer acids, 3-hydroxybutyric acid (3HB) and crotonic acid (CA), in water to propylene over solid acid catalysts using a packed-bed continuous-flow reactor. Propylene yields increase with increased Brønsted acidity of catalysts, with amorphous silica–alumina and niobium phosphate yielding 52 and 60 %C (percent feedstock carbon, max 75 %C) of feedstock 3HB and CA, respectively; additional products include CO 2 and retro-aldol products (acetaldehyde and acetic acid). Deactivation studies indicate progressive and permanent steam deactivation of amorphous silica–alumina, while re-calcination partially recovers niobium phosphate activity. Experiments demonstrating sustained reactor operation over niobium phosphate provide a promising technology pathway for increasing valorization of organic-rich wastewater. 

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4. Microwave spectrum and structure of a glyoxylic acid – formic acid complex☆

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5. Stability and mechanism of threose nucleic acid toward acid-mediated degradation

   https://doi.org/10.1093/nar/gkad716  

   Lee, Erica M.; Setterholm, Noah A.; Hajjar, Mohammad; Barpuzary, Bhawna; Chaput, John C. (August 2023, Nucleic Acids Research)

   Abstract Xeno-nucleic acids (XNAs) have gained significant interest as synthetic genetic polymers for practical applications in biomedicine, but very little is known about their biophysical properties. Here, we compare the stability and mechanism of acid-mediated degradation of α-l-threose nucleic acid (TNA) to that of natural DNA and RNA. Under acidic conditions and elevated temperature (pH 3.3 at 90°C), TNA was found to be significantly more resistant to acid-mediated degradation than DNA and RNA. Mechanistic insights gained by reverse-phase HPLC and mass spectrometry indicate that the resilience of TNA toward low pH environments is due to a slower rate of depurination caused by induction of the 2′-phosphodiester linkage. Similar results observed for 2′,5′-linked DNA and 2′-O-methoxy-RNA implicate the position of the phosphodiester group as a key factor in destabilizing the formation of the oxocarbenium intermediate responsible for depurination and strand cleavage of TNA. Biochemical analysis indicates that strand cleavage occurs by β-elimination of the 2′-phosphodiester linkage to produce an upstream cleavage product with a 2′-threose sugar and a downstream cleavage product with a 3′ terminal phosphate. This work highlights the unique physicochemical properties available to evolvable non-natural genetic polymers currently in development for biomedical applications. 

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