{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,16]],"date-time":"2026-09-16T14:08:20Z","timestamp":1789567700577,"version":"build-2803163510"},"reference-count":45,"publisher":"American Chemical Society (ACS)","issue":"36","license":[{"start":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T00:00:00Z","timestamp":1788393600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"funder":[{"DOI":"10.13039\/100000181","name":"Air Force Office of Scientific Research","doi-asserted-by":"publisher","award":["FA9550-22-1-0199"],"award-info":[{"award-number":["FA9550-22-1-0199"]}],"id":[{"id":"10.13039\/100000181","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,9,16]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>There has been recent interest in the physics of evaporating alcohol droplets under humid conditions. These studies focus on delineating time scales for different physical processes, but what about the chemistry? Given the novel reactivity of aqueous microdroplets, we surmise that there will also be interesting chemistry. Here we focus on the oxidation chemistry of single evaporating charged alcohol microdroplets, e.g., 1-nonanol, and find the formation of the corresponding aldehyde, carboxylic acid, and ester. Oxidation is observed only under humidified conditions, suggesting that water is the oxidant. This hypothesis is supported by isotope experiments using H218O. Furthermore, oxidation is charge-dependent with no oxidation products observed for alcohol microdroplets with minimal charge. We therefore propose a mechanism involving charge accumulation at the interface during evaporation followed by water adsorption and activation to yield hydroxyl radicals that initiate oxidation. Our findings reveal a critical role for water and interfacial charge in driving oxidation at the alcohol microdroplet interface, with broader implications for microdroplet reactivity and interfacial chemistry of nonaqueous microdroplets.<\/jats:p>","DOI":"10.1021\/jacs.6c11524","type":"journal-article","created":{"date-parts":[[2026,9,4]],"date-time":"2026-09-04T02:01:46Z","timestamp":1788487306000},"page":"38565-38569","source":"Crossref","is-referenced-by-count":0,"title":["Chemistry\nof Evaporating Charged Alcohol Microdroplets\nin Humid Environments"],"prefix":"10.1021","volume":"148","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-2628-8992","authenticated-orcid":true,"given":"Wen","family":"Zhang","sequence":"first","affiliation":[{"name":"University of California San Diego , , , ,","place":["La Jolla, California, United States, 92037"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2460-4370","authenticated-orcid":true,"given":"Kedong","family":"Gong","sequence":"additional","affiliation":[{"name":"University of California San Diego , , , ,","place":["La Jolla, California, United States, 92037"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5052-0045","authenticated-orcid":true,"given":"Vicki H.","family":"Grassian","sequence":"additional","affiliation":[{"name":"University of California San Diego , , , ,","place":["La Jolla, California, United States, 92037"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,3]]},"reference":[{"key":"2026091609115539600_cit1","doi-asserted-by":"publisher","first-page":"10585","DOI":"10.1021\/jacs.9b03227","article-title":"Micrometer-sized\nwater droplets induce spontaneous reduction","volume":"141","author":"Lee","year":"2019","journal-title":"J. Am. Chem. Soc."},{"key":"2026091609115539600_cit2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202400118","article-title":"Spontaneous oxidation in aqueous microdroplets: water\nradical cation as primary oxidizing agent","volume":"63","author":"Qiu","year":"2024","journal-title":"Angew.\nChem., Int. Ed."},{"key":"2026091609115539600_cit3","doi-asserted-by":"publisher","first-page":"11399","DOI":"10.1021\/jacs.5c01072","article-title":"Microdroplet chemistry with unactivated droplets","volume":"147","author":"Chen","year":"2025","journal-title":"J. Am. Chem. Soc."},{"key":"2026091609115539600_cit4","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202210765","article-title":"Simultaneous and spontaneous oxidation and reduction\nin microdroplets by the water radical cation\/anion pair","volume":"61","author":"Qiu","year":"2022","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026091609115539600_cit5","doi-asserted-by":"publisher","first-page":"19294","DOI":"10.1073\/pnas.1911883116","article-title":"Spontaneous generation\nof hydrogen peroxide from aqueous microdroplets","volume":"116","author":"Lee","year":"2019","journal-title":"Proc. Natl. Acad. Sci. U.S.A."},{"key":"2026091609115539600_cit6","doi-asserted-by":"publisher","first-page":"19862","DOI":"10.1002\/anie.202007736","article-title":"Accelerating\nelectrochemical reactions in a voltage-controlled interfacial microreactor","volume":"59","author":"Cheng","year":"2020","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026091609115539600_cit7","doi-asserted-by":"publisher","first-page":"31","DOI":"10.1146\/annurev-physchem-121319-110654","article-title":"Accelerated reaction kinetics in\nmicrodroplets: Overview and recent developments","volume":"71","author":"Wei","year":"2020","journal-title":"Annu. Rev. Phys. Chem."},{"key":"2026091609115539600_cit8","doi-asserted-by":"publisher","first-page":"10963","DOI":"10.1021\/jacs.4c02312","article-title":"Deciphering the microdroplet acceleration\nfactors of Aza-Michael addition reactions","volume":"146","author":"Song","year":"2024","journal-title":"J.\nAm. Chem. Soc."},{"key":"2026091609115539600_cit9","doi-asserted-by":"publisher","first-page":"149","DOI":"10.1146\/annurev-anchem-061622-030919","article-title":"An electrochemical\nperspective on reaction acceleration in microdroplets","volume":"17","author":"Vannoy","year":"2024","journal-title":"Annu. Rev. Anal. Chem."},{"key":"2026091609115539600_cit10","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.2501323122","article-title":"Accelerated\npeptide bond formation\nat air\u2013water interfaces","volume":"122","author":"Xia","year":"2025","journal-title":"Proc. Natl.\nAcad. Sci. U.S.A."},{"key":"2026091609115539600_cit11","doi-asserted-by":"publisher","first-page":"4929","DOI":"10.1021\/acs.jpca.1c02864","article-title":"Water\u2013air interfaces as environments\nto address the water paradox in prebiotic chemistry: A physical chemistry\nperspective","volume":"125","author":"Deal","year":"2021","journal-title":"J. Phys. Chem. A"},{"key":"2026091609115539600_cit12","doi-asserted-by":"publisher","first-page":"280","DOI":"10.1038\/s41467-021-27941-x","article-title":"Can electric\nfields drive chemistry\nfor an aqueous microdroplet?","volume":"13","author":"Hao","year":"2022","journal-title":"Nat. Commun."},{"key":"2026091609115539600_cit13","doi-asserted-by":"publisher","first-page":"18498","DOI":"10.1021\/jacs.4c04092","article-title":"Water microdroplets surrounded by\nalcohol vapor cause spontaneous oxidation of alcohols to organic peroxides","volume":"146","author":"Mofidfar","year":"2024","journal-title":"J. Am. Chem. Soc."},{"key":"2026091609115539600_cit14","doi-asserted-by":"publisher","DOI":"10.1126\/sciadv.adx4507","article-title":"Humidity drives\nspontaneous OH oxidation of organic particles","volume":"11","author":"Angelaki","year":"2025","journal-title":"Sci. Adv."},{"key":"2026091609115539600_cit15","doi-asserted-by":"publisher","first-page":"13026","DOI":"10.1039\/D0SC04611F","article-title":"A critical analysis of electrospray techniques for\nthe determination of accelerated rates and mechanisms of chemical\nreactions in droplets","volume":"11","author":"Rovelli","year":"2020","journal-title":"Chem. Sci."},{"key":"2026091609115539600_cit16","doi-asserted-by":"publisher","first-page":"6299","DOI":"10.1021\/jacs.4c15493","article-title":"The role of\ninterfaces and charge for chemical reactivity in microdroplets","volume":"147","author":"LaCour","year":"2025","journal-title":"J. Am. Chem. Soc."},{"key":"2026091609115539600_cit17","doi-asserted-by":"publisher","first-page":"622","DOI":"10.1021\/acscentsci.5c00306","article-title":"A source of the mysterious m\/z 36 ions identified:\nimplications for the stability of water and unusual chemistry in microdroplets","volume":"11","author":"Chen","year":"2025","journal-title":"ACS Cent. Sci."},{"key":"2026091609115539600_cit18","doi-asserted-by":"publisher","first-page":"17687","DOI":"10.1021\/acs.analchem.5c02973","article-title":"An alternative explanation for ions\nput forth as evidence\nfor abundant hydroxyl radicals formed due to the intrinsic electric\nfield at the surface of water droplets","volume":"97","author":"Chen","year":"2025","journal-title":"Anal.\nChem."},{"key":"2026091609115539600_cit19","doi-asserted-by":"publisher","first-page":"4529","DOI":"10.1021\/acs.jpca.5c02557","article-title":"Clarifying\nthe identity of the m\/z 36 ion in water microdroplet mass spectra","volume":"129","author":"Song","year":"2025","journal-title":"J. Phys. Chem. A"},{"key":"2026091609115539600_cit20","doi-asserted-by":"publisher","first-page":"18715","DOI":"10.1021\/jacs.5c21778","article-title":"A critical reappraisal of the evidence\nfor spontaneous\ngeneration of hydroxyl radicals in aqueous nanodroplets","volume":"148","author":"Purcell","year":"2026","journal-title":"J. Am. Chem. Soc."},{"key":"2026091609115539600_cit21","doi-asserted-by":"publisher","first-page":"20254","DOI":"10.1021\/jacs.6c05890","article-title":"Reactive ions in aqueous\nelectrospray microdroplet experiments originate from electrical discharge","volume":"148","author":"Zhang","year":"2026","journal-title":"J. Am. Chem. Soc."},{"key":"2026091609115539600_cit22","doi-asserted-by":"publisher","first-page":"2574","DOI":"10.1039\/D1SC06465G","article-title":"On the formation of hydrogen peroxide in water microdroplets","volume":"13","author":"Gallo","year":"2022","journal-title":"Chem. Sci."},{"key":"2026091609115539600_cit23","doi-asserted-by":"publisher","first-page":"35392","DOI":"10.1021\/jacs.5c09028","article-title":"Disentangling the roles of dissolved oxygen, common\nsalts, and pH on spontaneous hydrogen peroxide production in water:\nno O2, no H2O2","volume":"147","author":"Eatoo","year":"2025","journal-title":"J. Am. Chem. Soc."},{"key":"2026091609115539600_cit24","doi-asserted-by":"publisher","first-page":"3093","DOI":"10.1039\/D3SC06534K","article-title":"Busting the myth of spontaneous formation of H2O2 at the air\u2013water interface: contributions\nof the liquid\u2013solid interface and dissolved oxygen exposed","volume":"15","author":"Eatoo","year":"2024","journal-title":"Chem. Sci."},{"key":"2026091609115539600_cit25","doi-asserted-by":"publisher","first-page":"4476","DOI":"10.1021\/acs.jpclett.9b00757","article-title":"Titration of aerosol pH through droplet\ncoalescence","volume":"10","author":"Coddens","year":"2019","journal-title":"J. Phys. Chem. Lett."},{"key":"2026091609115539600_cit26","doi-asserted-by":"publisher","first-page":"10291","DOI":"10.1021\/acs.est.1c01932","article-title":"Enhanced\nrates of transition metal\nion catalyzed oxidation of S(IV) in aqueous aerosols: insights into\nsulfate aerosol formation in the atmosphere","volume":"55","author":"Angle","year":"2021","journal-title":"Environ. Sci. Technol."},{"key":"2026091609115539600_cit27","doi-asserted-by":"publisher","first-page":"316","DOI":"10.1039\/D2EA00092J","article-title":"Organic acid evaporation kinetics\nfrom aqueous aerosols: implications for aerosol buffering capacity\nin the atmosphere","volume":"3","author":"Angle","year":"2023","journal-title":"Environ. Sci.: Atmos."},{"key":"2026091609115539600_cit28","doi-asserted-by":"publisher","first-page":"6259","DOI":"10.1039\/D2SC06994F","article-title":"Direct quantification\nof changes in pH within single\nlevitated microdroplets and the kinetics of nitrate and chloride depletion","volume":"14","author":"Angle","year":"2023","journal-title":"Chem. Sci."},{"key":"2026091609115539600_cit29","doi-asserted-by":"publisher","first-page":"3069","DOI":"10.1021\/acs.jpca.6c00609","article-title":"Evolution\nof the composition and pH of single aqueous aerosols produced from\nbulk aqueous sulfite solutions","volume":"130","author":"Tam","year":"2026","journal-title":"J. Phys. Chem.\nA"},{"key":"2026091609115539600_cit30","doi-asserted-by":"publisher","first-page":"22317","DOI":"10.1021\/jacs.3c08249","article-title":"Size-dependent sigmoidal\nreaction kinetics for pyruvic acid condensation at the air\u2013water\ninterface in aqueous microdroplets","volume":"145","author":"Li","year":"2023","journal-title":"J. Am. Chem.\nSoc."},{"key":"2026091609115539600_cit31","doi-asserted-by":"publisher","first-page":"13429","DOI":"10.1039\/D4SC03014A","article-title":"Condensation\nkinetics in aqueous microdroplets driven\nby coupled interfacial reactions and gas-phase partitioning","volume":"15","author":"Li","year":"2024","journal-title":"Chem. Sci."},{"key":"2026091609115539600_cit32","doi-asserted-by":"publisher","first-page":"6424","DOI":"10.1021\/acs.jpca.5c03287","article-title":"The role\nof interfacial processes in accelerated reactions in nano- and micro-droplets","volume":"129","author":"Yang","year":"2025","journal-title":"J. Phys. Chem. A"},{"key":"2026091609115539600_cit33","doi-asserted-by":"publisher","first-page":"10540","DOI":"10.1021\/acs.jpca.5c04592","article-title":"Distinct oligomerization of lactic\nacid in aqueous\nmicrodroplets","volume":"129","author":"Roy","year":"2025","journal-title":"J. Phys. Chem. A"},{"key":"2026091609115539600_cit34","doi-asserted-by":"publisher","first-page":"19932","DOI":"10.1021\/acs.est.5c01509","article-title":"Size dependent uncatalyzed\nsulfite oxidation in aqueous\nmicrodroplets","volume":"59","author":"Gong","year":"2025","journal-title":"Environ. Sci. Technol."},{"key":"2026091609115539600_cit35","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.2302653120","article-title":"Evaporation of alcohol\ndroplets on surface in moist air","volume":"120","author":"Yang","year":"2023","journal-title":"Proc. Natl.\nAcad. Sci. U.S.A."},{"key":"2026091609115539600_cit36","doi-asserted-by":"publisher","DOI":"10.1016\/j.ijheatmasstransfer.2023.124118","article-title":"Evaporation of charged alcohol droplets suspended by\nelectrodynamic balance","volume":"209","author":"Ahumada-Lazo","year":"2023","journal-title":"Int. J. Heat Mass Transfer"},{"key":"2026091609115539600_cit37","doi-asserted-by":"publisher","first-page":"10807","DOI":"10.1021\/acs.jpca.5c04566","article-title":"Ester formation\nin alcohol microdroplet sprays: enhanced reactivity of C8 to C16 carboxylic acids with C1 to C3 alcohols and the effect of water","volume":"129","author":"Mehndiratta","year":"2025","journal-title":"J. Phys.\nChem. A"},{"key":"2026091609115539600_cit38","doi-asserted-by":"publisher","first-page":"74","DOI":"10.1021\/acsmeasuresciau.4c00033","article-title":"A comparison of different vibrational\nspectroscopic probes (ATR-FTIR, O-PTIR, Raman and AFM-IR) of lipids\nand other compounds found in environmental samples: case study of\nsubstrate-deposited sea spray aerosols","volume":"5","author":"Molina","year":"2025","journal-title":"ACS\nMeas. Sci. Au"},{"key":"2026091609115539600_cit39","doi-asserted-by":"publisher","first-page":"1435","DOI":"10.1016\/0017-9310(87)90175-X","article-title":"Alcohol droplet vaporization in humid\nair","volume":"30","author":"Law","year":"1987","journal-title":"Int. J. Heat Mass Transfer"},{"key":"2026091609115539600_cit40","doi-asserted-by":"publisher","first-page":"19430","DOI":"10.1039\/C8CP02521E","article-title":"Quantifying\nvapor transfer into evaporating\nethanol drops in a humid atmosphere","volume":"20","author":"Kita","year":"2018","journal-title":"Phys. Chem.\nChem. Phys."},{"key":"2026091609115539600_cit41","doi-asserted-by":"publisher","first-page":"16315","DOI":"10.1021\/jacs.3c04643","article-title":"Mechanism\nof hydrogen peroxide formation on sprayed water microdroplets","volume":"145","author":"Colussi","year":"2023","journal-title":"J. Am. Chem. Soc."},{"key":"2026091609115539600_cit42","doi-asserted-by":"publisher","first-page":"3366","DOI":"10.1021\/acs.jpclett.5c00434","article-title":"Physical\nchemistry of water microdroplets","volume":"16","author":"Colussi","year":"2025","journal-title":"J. Phys. Chem.\nLett."},{"key":"2026091609115539600_cit43","doi-asserted-by":"publisher","first-page":"6917","DOI":"10.1021\/ja101176r","article-title":"Hydrated electrons at the water\/air\ninterface","volume":"132","author":"Sagar","year":"2010","journal-title":"J. Am. Chem. Soc."},{"key":"2026091609115539600_cit44","doi-asserted-by":"publisher","first-page":"182","DOI":"10.1038\/s41467-023-44441-2","article-title":"Spectroscopy and\ndynamics of the hydrated electron at the water\/air interface","volume":"15","author":"Jordan","year":"2024","journal-title":"Nat. Commun."},{"key":"2026091609115539600_cit45","doi-asserted-by":"publisher","first-page":"29795","DOI":"10.1021\/jacs.6c03589","article-title":"Efficient\nhydrogen\nproduction from aqueous methanol driven by microdroplet interfaces","volume":"148","author":"Feng","year":"2026","journal-title":"J. Am. Chem. Soc."}],"container-title":["Journal of the American\nChemical Society"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jacs.6c11524","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/jacsat\/article-pdf\/148\/36\/38565\/68324083\/jacs.6c11524.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/jacsat\/article-pdf\/148\/36\/38565\/68324083\/jacs.6c11524.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,16]],"date-time":"2026-09-16T13:35:07Z","timestamp":1789565707000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/jacsat\/article\/148\/36\/38565\/5416095\/Chemistry-of-Evaporating-Charged-Alcohol"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,9,3]]},"references-count":45,"journal-issue":{"issue":"36","published-online":{"date-parts":[[2026,9,3]]},"published-print":{"date-parts":[[2026,9,16]]}},"URL":"https:\/\/doi.org\/10.1021\/jacs.6c11524","relation":{},"ISSN":["0002-7863","1520-5126"],"issn-type":[{"value":"0002-7863","type":"print"},{"value":"1520-5126","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,9,3]]}}}