Gas-Phase Formation of Water-Soluble Organic Compounds in the Atmosphere: A Retrosynthetic Analysis

Atmospheric particles contain a myriad of organiccompounds, including many multifunctional,water-soluble organic compounds. Many of thesecompounds are postulated to be secondary of origin. This work investigates the possible precursors ofseveral classes of multifunctional, water-solublesecondary organic compounds by analyzing the pathwaysleading to their formation, based on known gas-phasereactions. The analysis is termed `retrosynthetic'due to the backward direction of the analysis, fromproducts to precursors. Pathways for multi-functionalcompounds were generated combinatorially, consideringthe formation of one functional group at a time.Many multifunctional organic compounds with carboxylicacid, carbonyl, and hydroxy functional groups werefound to be first- or second-generation products ofcommon anthropogenic and biogenic volatile organiccompounds such as alkanes, alkenes, aromatics, andcyclic alkenes. The estimated yields of water-solubleorganic compounds from primary precursors ranged fromless than 1% to over 10%, based on stoichiometricconsiderations. The SOA formation index, whichcombines the concepts of yields and rates, was used tocompare the feasibility of the retrosyntheticpathways. Many of the candidate pathways involve theisomerization reaction of alkoxy radicals andoxygenated intermediate products such asmonocarboxylic acids and hydroxyaldehydes.