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Chloroanilines are persistent groundwater pollutants known to undergo reductive dechlorination under environmental conditions, yet their isotope fractionation remains unclear. This study reports multi-element isotopic fractionation (\u03b5) associated with reductive dechlorination of 2,3-dichloroaniline (2,3-DCA) and 2-chloroaniline (2-CA) using a Dehalobacter-dominated enrichment culture. During 2,3-DCA dechlorination, significant C (\u03b5C = \u22128.1 \u00b1 0.3\u2030) and Cl (\u03b5Cl = \u22127.5 \u00b1 0.1\u2030) isotope fractionation was observed (\u039bC\u2013Cl = 1.12 \u00b1 0.09), while N isotope fractionation was insignificant (\u0394\u03b415N &amp;lt; 1\u2030). Similarly, reductive dechlorination of 2-CA yielded \u03b5C = \u22128.9 \u00b1 0.3\u2030 and \u03b5Cl = \u221218.1 \u00b1 0.4\u2030 (\u039bC\u2013Cl = 0.48 \u00b1 0.03), with negligible changes in \u03b415N. The large and comparable apparent kinetic isotope effects for C and Cl may suggest that both reactions share similar transition-state characteristics, with C\u2013Cl bond cleavage as the rate-limiting step. In contrast to isotope fractionation reported for aerobic 2,3-DCA biodegradation, the distinct isotope patterns observed here enable differentiation between aerobic and anaerobic pathways. Using groundwater samples from a chloroaniline-impacted aquifer, we show that multi-element CSIA can help distinguish reductive dechlorination from aerobic biodegradation under spatially and temporally variable redox conditions.<\/jats:p>","DOI":"10.1021\/acs.est.6c05159","type":"journal-article","created":{"date-parts":[[2026,8,12]],"date-time":"2026-08-12T16:03:28Z","timestamp":1786550608000},"page":"23306-23318","source":"Crossref","is-referenced-by-count":0,"title":["Multi-Element\n(C, N, Cl) Stable Isotope Fractionation\nDuring Reductive Dechlorination of Chloroanilines"],"prefix":"10.1021","volume":"60","author":[{"given":"Shuping","family":"Wang","sequence":"first","affiliation":[{"name":"University of Toronto , , 35 St. George Street , , ,","place":["Toronto, Ontario, Canada, M5S 1A4"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"David","family":"Glo\u0308ckler","sequence":"additional","affiliation":[{"name":"University of Toronto , , 35 St. George Street , , ,","place":["Toronto, Ontario, Canada, M5S 1A4"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8114-8116","authenticated-orcid":true,"given":"Steffen","family":"Ku\u0308mmel","sequence":"additional","affiliation":[{"name":"Helmholtz Centre for Environmental Research\u2500UFZ , , ,","place":["Leipzig, Germany, 04318"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sofia P.","family":"Arau\u0301jo","sequence":"additional","affiliation":[{"name":"University of Toronto , , 200 College Street , , ,","place":["Toronto, Ontario, Canada, M5S 3E5"]},{"name":"Universidade Federal de Pernambuco , , , ,","place":["Recife, Pernambuco, Brazil, 50740-530"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Line","family":"Lomheim","sequence":"additional","affiliation":[{"name":"University of Toronto , , 200 College Street , , ,","place":["Toronto, Ontario, Canada, M5S 3E5"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lucas A. F. S.","family":"Ribeiro","sequence":"additional","affiliation":[{"name":"Geosyntec Consultants , 1243 Islington Ave, Suite 1201 , , ,","place":["Toronto, Ontario, Canada, M8X 1Y9"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"De\u0301bora","family":"Toledo Ramos","sequence":"additional","affiliation":[{"name":"Worley Consulting , , ,","place":["Sa\u0303o Paulo, Sa\u0303o Paulo, Brazil, 04794-000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Victor","family":"Gamez Grijalva","sequence":"additional","affiliation":[{"name":"Jacobs , 1501 West Fountainhead Parkway, Suite 401 , , ,","place":["Tempe, Arizona, United States, 85282"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8205-0842","authenticated-orcid":true,"given":"Lorenz","family":"Adrian","sequence":"additional","affiliation":[{"name":"Helmholtz Centre for Environmental Research\u2500UFZ , , ,","place":["Leipzig, Germany, 04318"]},{"name":"Technische Universita\u0308t Berlin , , ,","place":["Berlin, Germany, 13355"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"E. Erin","family":"Mack","sequence":"additional","affiliation":[{"name":"Corteva Agriscience , , , ,","place":["Wilmington, Delaware, United States, 19805"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8071-338X","authenticated-orcid":true,"given":"Elizabeth A.","family":"Edwards","sequence":"additional","affiliation":[{"name":"University of Toronto , , 200 College Street , , ,","place":["Toronto, Ontario, Canada, M5S 3E5"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6324-7233","authenticated-orcid":true,"given":"Elodie","family":"Passeport","sequence":"additional","affiliation":[{"name":"University of Toronto , , 35 St. George Street , , ,","place":["Toronto, Ontario, Canada, M5S 1A4"]},{"name":"University of Toronto , , 200 College Street , , ,","place":["Toronto, Ontario, Canada, M5S 3E5"]},{"name":"Rutgers University , , 14 College Farm Rd , , ,","place":["New Brunswick, New Jersey, United States, 08901"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,8,12]]},"reference":[{"key":"2026083119451365900_cit1","doi-asserted-by":"crossref","DOI":"10.1201\/9781420012613","volume-title":"Environmental\nIsotopes in Biodegradation and Bioremediation","author":"Aelion","year":"2009"},{"issue":"11","key":"2026083119451365900_cit2","doi-asserted-by":"publisher","first-page":"2005","DOI":"10.1039\/c0em00277a","article-title":"Stable Isotope\nFractionation to Investigate Natural Transformation Mechanisms of\nOrganic Contaminants: Principles, Prospects and Limitations","volume":"12","author":"Elsner","year":"2010","journal-title":"J. Environ. Monit."},{"key":"2026083119451365900_cit3","volume-title":"A Guide for Assessing\nBiodegradation and Source Identification of Organic Groundwater Contaminants\nUsing Compound Specific Isotope Analysis (CSIA)","author":"Hunkeler","year":"2009"},{"issue":"8","key":"2026083119451365900_cit4","doi-asserted-by":"publisher","first-page":"813","DOI":"10.1016\/S0146-6380(99)00064-9","article-title":"Contrasting\nCarbon Isotope Fractionation\nduring Biodegradation of Trichloroethylene and Toluene: Implications\nfor Intrinsic Bioremediation","volume":"30","author":"Lollar","year":"1999","journal-title":"Org. Geochem."},{"issue":"2","key":"2026083119451365900_cit5","doi-asserted-by":"publisher","first-page":"261","DOI":"10.1021\/es001227x","article-title":"Stable Carbon Isotope Evidence for\nIntrinsic Bioremediation of Tetrachloroethene and Trichloroethene\nat Area 6, Dover Air Force Base","volume":"35","author":"Lollar","year":"2001","journal-title":"Environ. Sci.\nTechnol."},{"issue":"1","key":"2026083119451365900_cit6","doi-asserted-by":"publisher","first-page":"14","DOI":"10.1038\/s44221-023-00176-4","article-title":"Perspectives of Compound-Specific\nIsotope Analysis of Organic Contaminants for Assessing Environmental\nFate and Managing Chemical Pollution","volume":"2","author":"Hofstetter","year":"2024","journal-title":"Nat. Water"},{"issue":"18","key":"2026083119451365900_cit7","doi-asserted-by":"publisher","first-page":"6896","DOI":"10.1021\/es0504587","article-title":"A New Concept\nLinking Observable Stable Isotope Fractionation to Transformation\nPathways of Organic Pollutants","volume":"39","author":"Elsner","year":"2005","journal-title":"Environ. Sci.\nTechnol."},{"key":"2026083119451365900_cit8","doi-asserted-by":"publisher","first-page":"128588","DOI":"10.1016\/j.jhydrol.2022.128588","article-title":"Compound Specific\nIsotope Analysis in Hydrogeology","volume":"615","author":"Phillips","year":"2022","journal-title":"J. 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Technol."},{"key":"2026083119451365900_cit17","doi-asserted-by":"publisher","first-page":"15251","DOI":"10.1021\/acs.est.5c04189","article-title":"Dehalobacter Dechlorinates\nDichloroanilines and Contributes to the Natural Attenuation of Dichloronitrobenzenes\nat a Complex Industrial Site","volume":"59","author":"Araujo","year":"2025","journal-title":"Environ. Sci.\nTechnol."},{"issue":"7","key":"2026083119451365900_cit18","doi-asserted-by":"publisher","first-page":"3714","DOI":"10.1021\/acs.est.6b05730","article-title":"Anaerobic Dehalogenation of Chloroanilines by Dehalococcoides Mccartyi Strain CBDB1 and Dehalobacter Strain 14DCB1 via Different Pathways as Related to Molecular Electronic\nStructure","volume":"51","author":"Zhang","year":"2017","journal-title":"Environ. Sci. 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Technol."},{"key":"2026083119451365900_cit21","doi-asserted-by":"publisher","first-page":"101","DOI":"10.1021\/es801759k","article-title":"Carbon and\nChlorine Isotope Fractionation\nduring Aerobic Oxidation and Reductive Dechlorination of Vinyl Chloride\nand Cis \u22121,2-Dichloroethene","volume":"43","author":"Abe","year":"2009","journal-title":"Environ. Sci. Technol."},{"issue":"11","key":"2026083119451365900_cit22","doi-asserted-by":"publisher","first-page":"8711","DOI":"10.1021\/acs.est.5c14706","article-title":"Mechanistic Insights into Anaerobic\nBiotransformation of Tris(2-Chloroethyl) Phosphate by Compound-Specific\nStable Isotope Analysis and Quantum Chemical Calculations","volume":"60","author":"Zhang","year":"2026","journal-title":"Environ. Sci. Technol."},{"issue":"16","key":"2026083119451365900_cit23","doi-asserted-by":"publisher","first-page":"9797","DOI":"10.1021\/acs.est.5b02602","article-title":"Isotope\nFractionation Associated with the Photochemical Dechlorination of\nChloroanilines","volume":"49","author":"Ratti","year":"2015","journal-title":"Environ. Sci. Technol."},{"issue":"27","key":"2026083119451365900_cit24","doi-asserted-by":"publisher","first-page":"12042","DOI":"10.1021\/acs.est.4c02173","article-title":"Compound-Specific Carbon, Nitrogen,\nand Hydrogen Isotope Analysis to Characterize Aerobic Biodegradation\nof 2,3-Dichloroaniline by a Mixed Enrichment Culture","volume":"58","author":"Suchana","year":"2024","journal-title":"Environ. Sci. Technol."},{"issue":"8","key":"2026083119451365900_cit25","doi-asserted-by":"publisher","first-page":"2663","DOI":"10.1128\/aem.58.8.2663-2666.1992","article-title":"Complete Mineralization\nof Benzene\nby Aquifer Microorganisms under Strictly Anaerobic Conditions","volume":"58","author":"Edwards","year":"1992","journal-title":"Appl. Environ. Microbiol."},{"key":"2026083119451365900_cit26","doi-asserted-by":"publisher","DOI":"10.1039\/9781839168666","volume-title":"Compound-Specific Stable\nIsotope Analysis","author":"Jochmann","year":"2012"},{"issue":"2","key":"2026083119451365900_cit27","doi-asserted-by":"publisher","first-page":"314","DOI":"10.1039\/C7JA00404D","article-title":"Online Isotope Analysis\nof37 Cl\/35 Cl Universally Applied for Semi-Volatile\nOrganic Compounds Using GC-MC-ICPMS","volume":"33","author":"Renpenning","year":"2018","journal-title":"J. Anal.\nAt. Spectrom."},{"issue":"17","key":"2026083119451365900_cit28","doi-asserted-by":"publisher","first-page":"9131","DOI":"10.1021\/acs.analchem.7b01875","article-title":"Compound Specific Stable\nChlorine Isotopic Analysis of Volatile Aliphatic Compounds Using Gas\nChromatography Hyphenated with Multiple Collector Inductively Coupled\nPlasma Mass Spectrometry","volume":"89","author":"Horst","year":"2017","journal-title":"Anal. Chem."},{"issue":"5","key":"2026083119451365900_cit29","doi-asserted-by":"publisher","first-page":"2832","DOI":"10.1021\/ac504232u","article-title":"Development and Validation of an\nUniversal Interface for Compound-Specific Stable Isotope Analysis\nof Chlorine (37 Cl\/35 Cl) by GC-High-Temperature\nConversion (HTC)-MS\/IRMS","volume":"87","author":"Renpenning","year":"2015","journal-title":"Anal. 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Q.\n          \n          Aerobic and\nAnaerobic Biotransformation of Chloroanilines, Chlorobenzenes, and\nDichlonitrobenzenes at a Complex Industrial Site in Brazil and Analysis\nof Associated Microbial Communities, Master Thesis; University of Toronto, 2018."},{"issue":"17","key":"2026083119451365900_cit32","doi-asserted-by":"publisher","first-page":"6801","DOI":"10.1021\/acs.analchem.2c05099","article-title":"Compound-Specific\nCarbon, Hydrogen, and Nitrogen Isotope\nAnalysis of Nitro- and Amino-Substituted Chlorobenzenes in Complex\nAqueous Matrices","volume":"95","author":"Suchana","year":"2023","journal-title":"Anal. Chem."},{"issue":"3","key":"2026083119451365900_cit33","doi-asserted-by":"publisher","first-page":"413","DOI":"10.1007\/BF02374138","article-title":"Experimental Determination of Nitrogen\nKinetic Isotope Fractionation: Some Principles; Illustration for the\nDenitrification and Nitrification Processes","volume":"62","author":"Mariotti","year":"1981","journal-title":"Plant Soil"},{"issue":"12","key":"2026083119451365900_cit34","doi-asserted-by":"publisher","first-page":"4731","DOI":"10.1021\/ac702543y","article-title":"Evaluating Chlorine Isotope Effects from Isotope Ratios\nand Mass Spectra of Polychlorinated Molecules","volume":"80","author":"Elsner","year":"2008","journal-title":"Anal. 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Phys."},{"issue":"14","key":"2026083119451365900_cit40","doi-asserted-by":"publisher","first-page":"9147","DOI":"10.1021\/acs.analchem.9b01756","article-title":"Sources of Uncertainty\nin Biotransformation Mechanistic Interpretations and Remediation Studies\nUsing CSIA","volume":"91","author":"Ojeda","year":"2019","journal-title":"Anal. Chem."},{"issue":"7","key":"2026083119451365900_cit41","doi-asserted-by":"publisher","first-page":"4263","DOI":"10.1021\/es505784a","article-title":"Isotope\nFractionation Associated with the Direct Photolysis\nof 4-Chloroaniline","volume":"49","author":"Ratti","year":"2015","journal-title":"Environ. Sci. Technol."},{"key":"2026083119451365900_cit42","doi-asserted-by":"publisher","first-page":"122956","DOI":"10.1016\/j.watres.2024.122956","article-title":"Hydrogen,\nNitrogen and Chlorine Isotope Fractionation\nduring 3-Chloroaniline Transformation in Aqueous Environments by Direct\nPhotolysis, TiO2 Photocatalysis and Hydrolysis","volume":"273","author":"Min","year":"2025","journal-title":"Water Res."},{"issue":"80","key":"2026083119451365900_cit43","doi-asserted-by":"publisher","first-page":"2326","DOI":"10.1021\/ja01542a075","article-title":"Kinetic Isotope\nEffects in the Acetolyses of Deuterated Cyclopentyl Tosylates1","volume":"80","author":"Streitwieser","year":"1958","journal-title":"J. Am. Chem. 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