{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,4]],"date-time":"2026-08-04T14:00:33Z","timestamp":1785852033876,"version":"3.56.0"},"reference-count":55,"publisher":"American Chemical Society (ACS)","issue":"30","license":[{"start":{"date-parts":[[2026,7,20]],"date-time":"2026-07-20T00:00:00Z","timestamp":1784505600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100017115","name":"Oakland University","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100017115","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000001","name":"National Science Foundation","doi-asserted-by":"publisher","award":["OCE-2042213"],"award-info":[{"award-number":["OCE-2042213"]}],"id":[{"id":"10.13039\/100000001","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,8,4]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Amines are key intermediates in biogeochemical nitrogen cycling and are potential precursors to amino acids and other biomolecules in hydrothermal systems on Earth and ocean worlds. While their reactivity and chemistry under high-temperature conditions have been previously studied, far less is known about how inorganic components such as metal ions and minerals influence amine stability and transformation pathways. Here, we investigate the hydrothermal reactivity of three representative amines (benzylamine, cyclohexylamine, and cyclohexylmethylamine) at 250 \u00b0C in the presence of Al-, Fe-, Mg-, and Zn- bearing minerals and metal salts. The amines exhibited moderate conversion and formed products including alcohols, alkenes, aldehydes, and diamines. Minerals and dissolved metal salts produced only minor enhancements or suppressions in total amine conversion and did not substantially alter product distributions or reaction pathways. These results indicate that small aliphatic and aromatic amines are not strongly affected by metal- and mineral-rich hydrothermal fluids. The limited influence of inorganic materials suggests that amines could persist and accumulate in hydrothermal environments, supporting their role as chemical precursors in prebiotic synthesis.<\/jats:p>","DOI":"10.1021\/acsomega.6c05119","type":"journal-article","created":{"date-parts":[[2026,7,20]],"date-time":"2026-07-20T18:25:28Z","timestamp":1784571928000},"page":"45477-45484","source":"Crossref","is-referenced-by-count":0,"title":["Stability of Amines\nwith Minerals and Metal Salts\nin Hydrothermal Fluids"],"prefix":"10.1021","volume":"11","author":[{"given":"Yiju","family":"Liao","sequence":"first","affiliation":[{"name":"Oakland University , , , ,","place":["Rochester, Michigan, United States, 48309"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alexandria","family":"Aspin","sequence":"additional","affiliation":[{"name":"Oakland University , , , ,","place":["Rochester, Michigan, United States, 48309"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0312-8408","authenticated-orcid":true,"given":"Ziming","family":"Yang","sequence":"additional","affiliation":[{"name":"Oakland University , , , ,","place":["Rochester, Michigan, United States, 48309"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,7,20]]},"reference":[{"issue":"6964","key":"2026080409243287200_cit1","doi-asserted-by":"publisher","first-page":"344","DOI":"10.1038\/nature02134","article-title":"Biological activity in the deep subsurface\nand the origin of heavy oil","volume":"426","author":"Head","year":"2003","journal-title":"Nature"},{"issue":"3","key":"2026080409243287200_cit2","doi-asserted-by":"publisher","first-page":"282","DOI":"10.1016\/j.mib.2011.04.013","article-title":"Archaeal diversity\nand community development in deep-sea\nhydrothermal vents","volume":"14","author":"Takai","year":"2011","journal-title":"Curr. Opin. Microbiol."},{"issue":"39","key":"2026080409243287200_cit3","doi-asserted-by":"publisher","first-page":"12036","DOI":"10.1073\/pnas.1504674112","article-title":"Fluid mixing and\nthe deep biosphere of a fossil Lost\nCity-type hydrothermal system at the Iberia Margin","volume":"112","author":"Klein","year":"2015","journal-title":"Proc. Natl. Acad. Sci. U. S. A."},{"issue":"5","key":"2026080409243287200_cit4","doi-asserted-by":"publisher","first-page":"271","DOI":"10.1038\/s41579-019-0160-2","article-title":"The microbiomes\nof deep-sea hydrothermal vents: distributed globally, shaped locally","volume":"17","author":"Dick","year":"2019","journal-title":"Nat. Rev. Microbiol."},{"key":"2026080409243287200_cit5","doi-asserted-by":"publisher","first-page":"207","DOI":"10.1038\/nature14262","article-title":"Ongoing\nhydrothermal\nactivities within Enceladus","volume":"519","author":"Hsu","year":"2015","journal-title":"Nature"},{"issue":"6334","key":"2026080409243287200_cit6","doi-asserted-by":"publisher","first-page":"155","DOI":"10.1126\/science.aai8703","article-title":"Cassini finds molecular\nhydrogen in the Enceladus plume:\nevidence for hydrothermal processes","volume":"356","author":"Waite","year":"2017","journal-title":"Science"},{"issue":"7711","key":"2026080409243287200_cit7","doi-asserted-by":"publisher","first-page":"564","DOI":"10.1038\/s41586-018-0246-4","article-title":"Macromolecular\norganic compounds from the depths of\nEnceladus","volume":"558","author":"Postberg","year":"2018","journal-title":"Nature"},{"issue":"5383","key":"2026080409243287200_cit8","doi-asserted-by":"publisher","first-page":"1659","DOI":"10.1126\/science.281.5383.1659","article-title":"Energetics of amino\nacid synthesis in hydrothermal\necosystems","volume":"281","author":"Amend","year":"1998","journal-title":"Science"},{"key":"2026080409243287200_cit9","doi-asserted-by":"publisher","first-page":"805","DOI":"10.1038\/nrmicro1991","article-title":"Hydrothermal vents\nand the origin of life","volume":"6","author":"Martin","year":"2008","journal-title":"Nat. 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Geochem."},{"issue":"6487","key":"2026080409243287200_cit13","doi-asserted-by":"publisher","first-page":"285","DOI":"10.1038\/370285a0","article-title":"Evidence\nfor metastable equilibrium between hydrocarbons under hydrothermal\nconditions","volume":"370","author":"Seewald","year":"1994","journal-title":"Nature"},{"issue":"17","key":"2026080409243287200_cit14","doi-asserted-by":"publisher","first-page":"7861","DOI":"10.1021\/jo500899x","article-title":"Hydrothermal photochemistry as a\nmechanistic tool in organic geochemistry: the chemistry of dibenzyl\nketone","volume":"79","author":"Yang","year":"2014","journal-title":"J. Org. Chem."},{"key":"2026080409243287200_cit15","doi-asserted-by":"publisher","first-page":"597","DOI":"10.1016\/j.gca.2019.11.003","article-title":"Mechanisms\nof decarboxylation of phenylacetic acids and their sodium salts in\nwater at high temperature and pressure","volume":"269","author":"Glein","year":"2020","journal-title":"Geochim.\nCosmochim. 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Lett."},{"issue":"24","key":"2026080409243287200_cit22","doi-asserted-by":"publisher","first-page":"12159","DOI":"10.1021\/acs.joc.5b02109","article-title":"Organic oxidations\nusing geomimicry","volume":"80","author":"Yang","year":"2015","journal-title":"J. Org. Chem."},{"key":"2026080409243287200_cit23","doi-asserted-by":"crossref","DOI":"10.1021\/acsinfocus.7e7023","volume-title":"Hydrothermal\nChemistry","author":"Yang","year":"2023"},{"key":"2026080409243287200_cit24","doi-asserted-by":"publisher","first-page":"113","DOI":"10.1016\/j.gca.2018.09.020","article-title":"Deamination\nreaction mechanisms of protonated amines\nunder hydrothermal conditions","volume":"244","author":"Robinson","year":"2019","journal-title":"Geochim. Cosmochim.\nActa"},{"key":"2026080409243287200_cit25","doi-asserted-by":"publisher","first-page":"318","DOI":"10.1016\/j.gca.2021.01.038","article-title":"Quantifying the\nextent of amide and peptide bond synthesis\nacross conditions relevant to geologic and planetary environments","volume":"300","author":"Robinson","year":"2021","journal-title":"Geochim. Cosmochim. 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Acta"},{"key":"2026080409243287200_cit31","doi-asserted-by":"publisher","first-page":"105060","DOI":"10.1016\/j.orggeochem.2025.105060","article-title":"Deamination\nof alicyclic and aromatic amines under geologically relevant hydrothermal\nconditions","volume":"209","author":"Liao","year":"2025","journal-title":"Org. Geochem."},{"key":"2026080409243287200_cit32","doi-asserted-by":"publisher","first-page":"44","DOI":"10.1016\/j.gca.2025.04.024","article-title":"Survivability and pathways\nof amino acids in oceanic hydrothermal systems: A mechanistic study\nof phenylalanine","volume":"398","author":"Aspin","year":"2025","journal-title":"Geochim. Cosmochim. Acta"},{"key":"2026080409243287200_cit33","doi-asserted-by":"publisher","first-page":"330","DOI":"10.1016\/j.gca.2012.11.008","article-title":"The influence\nof minerals on decomposition of the n-alkyl-\u03b1-amino acid norvaline\nunder hydrothermal conditions","volume":"104","author":"McCollom","year":"2013","journal-title":"Geochim. Cosmochim.\nActa"},{"issue":"10","key":"2026080409243287200_cit34","doi-asserted-by":"publisher","first-page":"2225","DOI":"10.1016\/0016-7037(94)90007-8","article-title":"Hydrothermal circulation\nthrough mid-ocean ridge flanks:\nFluxes of heat and magnesium","volume":"58","author":"Mottl","year":"1994","journal-title":"Geochim. Cosmochim.\nActa"},{"key":"2026080409243287200_cit35","doi-asserted-by":"publisher","first-page":"145","DOI":"10.1038\/ngeo1088","article-title":"Metal flux from hydrothermal vents increased by organic\ncomplexation","volume":"4","author":"Sander","year":"2011","journal-title":"Nat. Geosci."},{"issue":"2","key":"2026080409243287200_cit36","doi-asserted-by":"publisher","first-page":"109","DOI":"10.1007\/s11084-008-9154-1","article-title":"An evaluation\nof the critical parameters\nfor abiotic peptide synthesis in submarine hydrothermal systems","volume":"39","author":"Cleaves","year":"2009","journal-title":"Origins Life Evol. Biospheres"},{"key":"2026080409243287200_cit37","doi-asserted-by":"publisher","DOI":"10.3791\/58230-v","article-title":"An experimental protocol for studying\nmineral effects on organic\nhydrothermal transformations","volume":"138","author":"Yang","year":"2018","journal-title":"JoVE"},{"key":"2026080409243287200_cit100","doi-asserted-by":"publisher","first-page":"105293","DOI":"10.1016\/j.apgeochem.2022.105293","article-title":"Effects of magnetite on phosphorus\nstorage and carbon cycling in Lake Michigan shoreline sediments","volume":"140","author":"Zaporski","year":"2022","journal-title":"Appl. Geochem."},{"issue":"8","key":"2026080409243287200_cit38","doi-asserted-by":"publisher","first-page":"1997","DOI":"10.1021\/acsearthspacechem.1c00104","article-title":"Hydrothermal\nexperiments with protonated benzylamines provide predictions of temperature-dependent\ndeamination rates for geochemical modeling","volume":"5","author":"Robinson","year":"2021","journal-title":"ACS Earth Space Chem."},{"issue":"8","key":"2026080409243287200_cit39","doi-asserted-by":"publisher","first-page":"2009","DOI":"10.1016\/0016-7037(88)90181-0","article-title":"Calculation of the\nthermodynamic and transport properties\nof aqueous species at high pressures and temperatures: Correlation\nalgorithms for ionic species and equation of state predictions to\n5 kb and 1000 \u00b0C","volume":"52","author":"Shock","year":"1988","journal-title":"Geochim. Cosmochim. Acta"},{"issue":"5","key":"2026080409243287200_cit40","doi-asserted-by":"publisher","first-page":"907","DOI":"10.1016\/S0016-7037(96)00339-0","article-title":"Inorganic\nspecies in geologic fluids: Correlations among standard molal thermodynamic\nproperties of aqueous ions and hydroxide complexes","volume":"61","author":"Shock","year":"1997","journal-title":"Geochim. Cosmochim. Acta"},{"issue":"7","key":"2026080409243287200_cit41","doi-asserted-by":"publisher","first-page":"899","DOI":"10.1016\/0098-3004(92)90029-Q","article-title":"SUPCRT92: A software\npackage for\ncalculating the standard molal thermodynamic properties of minerals,\ngases, aqueous species, and reactions from 1 to 5000 bar and 0 to\n1000\u00b0C","volume":"18","author":"Johnson","year":"1992","journal-title":"Comput. Geosci."},{"key":"2026080409243287200_cit42","doi-asserted-by":"crossref","unstructured":"Wolery, T. J.\n          \n          EQ 3\/6,\na software package for geochemical modeling of aqueous systems: package\noverview and installation guide (version 7.0); Lawrence Livermore National Lab., 1992.","DOI":"10.2172\/138894"},{"issue":"9","key":"2026080409243287200_cit43","doi-asserted-by":"publisher","first-page":"1596","DOI":"10.1021\/acsearthspacechem.0c00150","article-title":"Effect of copper salts\non amide hydrothermal formation and reactivity","volume":"4","author":"Fu","year":"2020","journal-title":"ACS Earth Space Chem."},{"key":"2026080409243287200_cit44","doi-asserted-by":"publisher","first-page":"62","DOI":"10.1016\/j.gca.2024.03.013","article-title":"Thermodynamic\nproperty estimations for aqueous primary, secondary, and tertiary\nalkylamines, benzylamines, and their corresponding aminiums across\ntemperature and pressure are validated by measurements from experiments","volume":"372","author":"Robinson","year":"2024","journal-title":"Geochim. Cosmochim. Acta"},{"issue":"12","key":"2026080409243287200_cit45","doi-asserted-by":"publisher","first-page":"4996","DOI":"10.1021\/la036288y","article-title":"Adsorption\nof organic\nmatter at mineral\/water interfaces. 2. Outer-sphere adsorption of\nmaleate and implications for dissolution processes","volume":"20","author":"Johnson","year":"2004","journal-title":"Langmuir"},{"issue":"7","key":"2026080409243287200_cit46","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.2316569121","article-title":"Electrostatic coupling and water\nbridging in adsorption hierarchy of biomolecules at water\u2013clay\ninterfaces","volume":"121","author":"Wang","year":"2024","journal-title":"Proc. Natl. Acad. Sci. U. S. A."},{"issue":"5","key":"2026080409243287200_cit47","doi-asserted-by":"publisher","first-page":"a002162","DOI":"10.1101\/cshperspect.a002162","article-title":"Mineral\nsurfaces, geochemical complexities, and the\norigins of life","volume":"2","author":"Hazen","year":"2010","journal-title":"Cold Spring Harbor Perspect.\nBiol."},{"issue":"1","key":"2026080409243287200_cit48","doi-asserted-by":"publisher","first-page":"13","DOI":"10.3390\/soilsystems5010013","article-title":"Sorption\nmechanisms of chemicals in soils","volume":"5","author":"Strawn","year":"2021","journal-title":"Soil Syst."},{"issue":"8","key":"2026080409243287200_cit49","doi-asserted-by":"publisher","first-page":"3093","DOI":"10.1016\/0016-7037(92)90291-P","article-title":"Dissolution and\nprecipitation kinetics of gibbsite\nat 80\u00b0C and pH 3: The dependence on solution saturation state","volume":"56","author":"Nagy","year":"1992","journal-title":"Geochim. Cosmochim. Acta"},{"issue":"10.7185","key":"2026080409243287200_cit50","doi-asserted-by":"publisher","first-page":"1","DOI":"10.7185\/geochemlet.2035","article-title":"Brucite formation and\ndissolution\nin oceanic serpentinite","volume":"16","author":"Klein","year":"2020","journal-title":"Geochem. Perspect.\nLett."},{"issue":"17","key":"2026080409243287200_cit51","doi-asserted-by":"publisher","first-page":"4813","DOI":"10.1021\/om400523f","article-title":"Benzyl cation\nstabilized by metal complexation. Relative stability of coordinated\nmethylene arenium, \u03c0-benzylic, and \u03c3-benzylic structures","volume":"32","author":"Poverenov","year":"2013","journal-title":"Organometallics"},{"issue":"5","key":"2026080409243287200_cit52","doi-asserted-by":"publisher","first-page":"355","DOI":"10.1111\/j.1472-4669.2010.00249.x","article-title":"Serpentinization as a source of energy\nat the origin of life","volume":"8","author":"Russell","year":"2010","journal-title":"Geobiology"},{"key":"2026080409243287200_cit101","doi-asserted-by":"publisher","first-page":"e202500508","DOI":"10.1002\/open.202500508","article-title":"Synthesis\nof amides\nfrom amines and esters under hydrothermal conditions","volume":"15","author":"Brown","year":"2026","journal-title":"ChemistryOpen"},{"issue":"1\u20133","key":"2026080409243287200_cit53","doi-asserted-by":"publisher","first-page":"161","DOI":"10.1007\/BF01581580","article-title":"Thermodynamics of Strecker synthesis in hydrothermal systems","volume":"25","author":"Schulte","year":"1995","journal-title":"Origins Life Evol. Biosphere"}],"container-title":["ACS Omega"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acsomega.6c05119","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/acsodf\/article-pdf\/11\/30\/45477\/66067330\/acsomega.6c05119.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/acsodf\/article-pdf\/11\/30\/45477\/66067330\/acsomega.6c05119.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,8,4]],"date-time":"2026-08-04T13:36:17Z","timestamp":1785850577000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/acsodf\/article\/11\/30\/45477\/5222550\/Stability-of-Amines-with-Minerals-and-Metal-Salts"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,7,20]]},"references-count":55,"journal-issue":{"issue":"30","published-online":{"date-parts":[[2026,7,20]]},"published-print":{"date-parts":[[2026,8,4]]}},"URL":"https:\/\/doi.org\/10.1021\/acsomega.6c05119","relation":{},"ISSN":["2470-1343"],"issn-type":[{"value":"2470-1343","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,7,20]]}}}