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Sorption behavior, bioaccumulation, and environmental longevity of ionogenic molecules like FASAs is governed by the acid dissociation constant (pKa). However, limited experimental pKa values are available for FASAs, with most values computationally modeled with unknown accuracy. In this research 19F Nuclear Magnetic Resonance (NMR) spectroscopy was used to experimentally determine the pKa of perfluorobutane sulfonamide (FBSA) (6.22 \u00b1 0.06), N-methyl (Me) FBSA (7.46 \u00b1 0.03), perfluorohexane sulfonamide (FHxSA) (6.22 \u00b1 0.04), perfluorooctane sulfonamide (FOSA) (6.4 \u00b1 0.3), Me-FOSA (7.7 \u00b1 0.3), and N-ethyl FOSA (8.0 \u00b1 0.3). The pKa of low aqueous solubility FASAs (FOSA, MeFOSA, and EtFOSA) were determined using acetonitrile (ACN):aqueous buffer mixtures and an aggregated mathematical approach developed to simultaneously fit the data for 40, 50, and 60% ACN. Fluorinated carbon number did not significantly impact pKa. Methyl substitution of nitrogen (MeFBSA) increased the pKa by 1.24 log units for C4 and 1.3 log units for C8 FASAs. Ethyl substitution increased the pKa by 1.6 log units (FOSA vs EtFOSA). Experimentally measured values were compared to four different prediction models. Our internally corrected DFT model gave the best agreement with experimental values while Chemicalize gave pKa values up to 4 log units lower than experimental values.<\/jats:p>","DOI":"10.1021\/acs.est.6c08545","type":"journal-article","created":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T12:20:52Z","timestamp":1788438052000},"page":"25775-25785","source":"Crossref","is-referenced-by-count":0,"title":["Experimental\np\n                    <i>K<\/i>\n                    a Values\nof Substituted and Unsubstituted Perfluoroalkyl Sulfonamides Via 19F NMR"],"prefix":"10.1021","volume":"60","author":[{"given":"E. E.","family":"Hernandez","sequence":"first","affiliation":[{"name":"Oregon State University , , , ,","place":["Corvallis, Oregon, United States, 97331"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"X.","family":"Li","sequence":"additional","affiliation":[{"name":"Oregon State University , , , ,","place":["Corvallis, Oregon, United States, 97331"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6137-3367","authenticated-orcid":true,"given":"I. E.","family":"Logan","sequence":"additional","affiliation":[{"name":"Oregon State University , , , ,","place":["Corvallis, Oregon, United States, 97331"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8702-1602","authenticated-orcid":true,"given":"S.","family":"Endo","sequence":"additional","affiliation":[{"name":"National Institute for Environmental Studies , , Onogawa 16-2 , , ,","place":["Tsukuba, Ibaraki, Japan, 305-8506"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"I.","family":"Spackman","sequence":"additional","affiliation":[{"name":"Colorado School of Mines , , , ,","place":["Golden, Colorado, United States, 80401"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"S.","family":"Hubbard","sequence":"additional","affiliation":[{"name":"Oregon State University , , , ,","place":["Corvallis, Oregon, United States, 97331"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6925-9868","authenticated-orcid":true,"given":"P.","family":"Sengupta","sequence":"additional","affiliation":[{"name":"Oregon State University , , , ,","place":["Corvallis, Oregon, United States, 97331"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3385-6676","authenticated-orcid":true,"given":"D.","family":"Koley","sequence":"additional","affiliation":[{"name":"Oregon State University , , , ,","place":["Corvallis, Oregon, United States, 97331"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5849-8919","authenticated-orcid":true,"given":"S.","family":"Vyas","sequence":"additional","affiliation":[{"name":"Colorado School of Mines , , , ,","place":["Golden, Colorado, United States, 80401"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"L.","family":"Xue","sequence":"additional","affiliation":[{"name":"Oregon State University , , , ,","place":["Corvallis, Oregon, United States, 97331"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9346-4693","authenticated-orcid":true,"given":"J.","family":"Field","sequence":"additional","affiliation":[{"name":"Oregon State University , , , ,","place":["Corvallis, Oregon, United States, 97331"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6858-0086","authenticated-orcid":true,"given":"P. N.","family":"Reardon","sequence":"additional","affiliation":[{"name":"Oregon State University , , , ,","place":["Corvallis, Oregon, United States, 97331"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,1]]},"reference":[{"key":"2026091511105036600_cit1","doi-asserted-by":"publisher","first-page":"513","DOI":"10.1002\/ieam.258","article-title":"Perfluoroalkyl\nand Polyfluoroalkyl Substances in the\nEnvironment: Terminology, Classifications, and Origins","volume":"7","author":"Buck","year":"2011","journal-title":"Integr. Environ. Assess. Manage."},{"issue":"3","key":"2026091511105036600_cit2","doi-asserted-by":"publisher","DOI":"10.1029\/2021RG000765","article-title":"Per- and Polyfluoroalkyl Substances\n(PFAS) in Subsurface Environments: Occurrence, Fate, Transport, and\nResearch Prospect","volume":"60","author":"Lyu","year":"2022","journal-title":"Rev. Geophys."},{"issue":"11","key":"2026091511105036600_cit3","doi-asserted-by":"publisher","first-page":"6184","DOI":"10.1021\/es500169x","article-title":"In Vitro Metabolic Formation of Perfluoroalkyl Sulfonamides\nfrom Copolymer Surfactants of Pre- and Post-2002 Scotchgard Fabric\nProtector Products","volume":"48","author":"Chu","year":"2014","journal-title":"Environ. Sci. Technol."},{"key":"2026091511105036600_cit4","doi-asserted-by":"publisher","first-page":"168183","DOI":"10.1016\/j.cej.2025.168183","article-title":"PFAS in the textile industry: Sources, fate, detection,\nand pathways toward sustainable remediation and regulation","volume":"522","author":"Pervez","year":"2025","journal-title":"Chem. Eng. J."},{"key":"2026091511105036600_cit5","doi-asserted-by":"publisher","first-page":"121851","DOI":"10.1016\/j.envres.2025.121851","article-title":"Environmental occurrence of perfluorooctanesulfonic\nacid from sulfluramid-based ant bait usage and its ecotoxicological\nrisks","volume":"279","author":"Guida","year":"2025","journal-title":"Environ. Res."},{"issue":"13","key":"2026091511105036600_cit6","doi-asserted-by":"publisher","first-page":"4600","DOI":"10.1021\/es062792o","article-title":"Bioaccumulation\nof perfluorochemicals in sediments by the aquatic oligochaete Lumbriculds\nvariegatus","volume":"41","author":"Higgins","year":"2007","journal-title":"Environ. Sci. Technol."},{"key":"2026091511105036600_cit7","doi-asserted-by":"publisher","first-page":"146444","DOI":"10.1016\/j.scitotenv.2021.146444","article-title":"Transport\nof PFOS in aquifer sediment: Transport behavior and a distributed-sorption\nmodel","volume":"779","author":"Wang","year":"2021","journal-title":"Sci. Total Environ."},{"issue":"10","key":"2026091511105036600_cit8","doi-asserted-by":"publisher","first-page":"6580","DOI":"10.1021\/acs.est.1c01543","article-title":"The Case\nfor Direct Measures of Soil-to-Groundwater Contaminant Mass Discharge\nat AFFF-Impacted Sites","volume":"55","author":"Anderson","year":"2021","journal-title":"Environ. Sci. Technol."},{"issue":"4","key":"2026091511105036600_cit9","doi-asserted-by":"publisher","first-page":"2047","DOI":"10.1021\/acs.est.6b05843","article-title":"Discovery of 40\nClasses of Per- and Polyfluoroalkyl\nSubstances in Historical Aqueous Film-Forming Foams (AFFFs) and AFFF-Impacted\nGroundwater","volume":"51","author":"Barzen-Hanson","year":"2017","journal-title":"Environ. Sci. Technol."},{"issue":"21","key":"2026091511105036600_cit10","doi-asserted-by":"publisher","first-page":"13590","DOI":"10.1021\/acs.est.0c03117","article-title":"Aqueous\nFilm-Forming Foams Exhibit\nGreater Interfacial Activity than PFOA, PFOS, or FOSA","volume":"54","author":"Costanza","year":"2020","journal-title":"Environ. Sci. Technol."},{"key":"2026091511105036600_cit11","doi-asserted-by":"publisher","first-page":"444","DOI":"10.1016\/j.scitotenv.2016.07.010","article-title":"Uptake of perfluorooctanoic\nacid, perfluorooctane sulfonate and perfluorooctane sulfonamide by\ncarrot and lettuce from compost amended soil","volume":"571","author":"Bizkarguenaga","year":"2016","journal-title":"Sci. Total Environ."},{"key":"2026091511105036600_cit12","doi-asserted-by":"publisher","first-page":"38","DOI":"10.1016\/j.scitotenv.2017.06.111","article-title":"Per- and poly-fluoroalkyl\ncompounds in freshwater fish from the Rhone River: Influence of fish\nsize, diet, prey contamination and biotransformation","volume":"605","author":"Babut","year":"2017","journal-title":"Sci. Total Environ."},{"issue":"4","key":"2026091511105036600_cit13","doi-asserted-by":"publisher","first-page":"350","DOI":"10.1021\/acs.estlett.4c00143","article-title":"Bioaccumulation\nof Perfluoroalkyl\nSulfonamides (FASA)","volume":"11","author":"Pickard","year":"2024","journal-title":"Environ. Sci. Technol.\nLett."},{"issue":"12","key":"2026091511105036600_cit14","doi-asserted-by":"publisher","first-page":"8139","DOI":"10.1021\/acs.est.1c00522","article-title":"Unsaturated\nPFOS and Other PFASs\nin Human Serum and Drinking Water from an AFFF-Impacted Community","volume":"55","author":"McDonough","year":"2021","journal-title":"Environ. Sci. Technol."},{"issue":"1","key":"2026091511105036600_cit15","doi-asserted-by":"publisher","first-page":"dvac010","DOI":"10.1093\/eep\/dvac010","article-title":"Nephrotoxicity of perfluorooctane sulfonate (PFOS)\neffect on transcription and epigenetic factors","volume":"8","author":"Wen","year":"2022","journal-title":"Environ. Epigenet."},{"key":"2026091511105036600_cit16","doi-asserted-by":"publisher","first-page":"132552","DOI":"10.1016\/j.jhazmat.2023.132552","article-title":"Hepatotoxic\nresponse of perfluorooctane sulfonamide\n(PFOSA) in early life stage zebrafish (Danio rerio) is greater than\nperfluorooctane sulfonate (PFOS)","volume":"461","author":"Xuan","year":"2024","journal-title":"J. Hazard.\nMater."},{"issue":"2","key":"2026091511105036600_cit17","doi-asserted-by":"publisher","first-page":"323","DOI":"10.1016\/j.envpol.2004.12.020","article-title":"Preliminary\nscreening of perfluorooctane sulfonate\n(PFOS) and other fluorochemicals in fish, birds and marine mammals\nfrom Greenland and the Faroe Islands","volume":"136","author":"Bossi","year":"2005","journal-title":"Environ.\nPollut."},{"key":"2026091511105036600_cit18","doi-asserted-by":"publisher","first-page":"393","DOI":"10.1016\/j.scitotenv.2017.01.079","article-title":"Concentrations and\npatterns of perfluoroalkyl and polyfluoroalkyl substances in a river\nand three drinking water treatment plants near and far from a major\nproduction source","volume":"583","author":"Boiteux","year":"2017","journal-title":"Sci. Total Environ."},{"issue":"3","key":"2026091511105036600_cit19","doi-asserted-by":"publisher","first-page":"748","DOI":"10.1021\/es051799n","article-title":"Is fish a major source of fluorinated\nsurfactants and\nrepellents in humans living on the Baltic coast?","volume":"40","author":"Falandysz","year":"2006","journal-title":"Environ. Sci. Technol."},{"key":"2026091511105036600_cit20","doi-asserted-by":"publisher","first-page":"128615","DOI":"10.1016\/j.jhazmat.2022.128615","article-title":"Systematic developmental toxicity assessment of a structurally\ndiverse library of PFAS in zebrafish","volume":"431","author":"Truong","year":"2022","journal-title":"J. Hazard.\nMater."},{"key":"2026091511105036600_cit21","doi-asserted-by":"publisher","first-page":"113550","DOI":"10.1016\/j.envpol.2019.113550","article-title":"High-content\nscreening in zebrafish identifies perfluorooctanesulfonamide as a\npotent developmental toxicant","volume":"256","author":"Dasgupta","year":"2020","journal-title":"Environ. Pollut."},{"key":"2026091511105036600_cit22","doi-asserted-by":"crossref","volume-title":"Environmental\nOrganic Chemistry","author":"Schwarzenbach","DOI":"10.1002\/0471649643"},{"issue":"13","key":"2026091511105036600_cit23","doi-asserted-by":"publisher","first-page":"5032","DOI":"10.1021\/es8011904","article-title":"The pKa values of PFOA and other highly fluorinated\ncarboxylic acids (vol 73, pg 2323, 1951)","volume":"42","author":"Goss","year":"2008","journal-title":"Environ.\nSci. Technol."},{"issue":"24","key":"2026091511105036600_cit24","doi-asserted-by":"publisher","first-page":"9283","DOI":"10.1021\/es802047v","article-title":"Experimental\npKa Determination for Perfluorooctanoic\nAcid (PFOA) and the Potential Impact of pKa Concentration Dependence on Laboratory-Measured Partitioning Phenomena\nand Environmental Modeling","volume":"42","author":"Burns","year":"2008","journal-title":"Environ. Sci. Technol."},{"issue":"13","key":"2026091511105036600_cit25","doi-asserted-by":"publisher","first-page":"1388","DOI":"10.1080\/10934520903217278","article-title":"A new class of perfluorinated\nacid contaminants: Primary\nand secondary substituted perfluoroalkyl sulfonamides are acidic at\nenvironmentally and toxicologically relevant pH values","volume":"44","author":"Rayne","year":"2009","journal-title":"J. Environ. Sci. Health Part A"},{"key":"2026091511105036600_cit26","unstructured":"Final Report: Summary of Physical\/Chemical and Environmental\nParameters\nfor PFAS: Subject to Interim Special Order by Consent No. 20\u2013086-CWP\/AP\/GW\/HW\/DW\/SW,\nParagraph 37(J)(3). Laboratory Request Number: E21\u20130037. https:\/\/rais.ornl.gov\/documents\/3M.pdf(accessed May 20, 2026)."},{"issue":"36","key":"2026091511105036600_cit27","doi-asserted-by":"publisher","first-page":"24745","DOI":"10.1039\/D3CP01390A","article-title":"pKa prediction of per- and polyfluoroalkyl acids\nin water using in silico gas phase stretching vibrational frequencies\nand infrared intensities","volume":"25","author":"Murillo-Gelvez","year":"2023","journal-title":"Phys. Chem. Chem.\nPhys."},{"issue":"8","key":"2026091511105036600_cit28","doi-asserted-by":"publisher","first-page":"1094","DOI":"10.1021\/jo00922a017","article-title":"Acidites and\npartition coefficients\nof fluoromethanesulfonamides","volume":"39","author":"Trepka","year":"1974","journal-title":"J. Org. Chem."},{"issue":"22","key":"2026091511105036600_cit29","doi-asserted-by":"publisher","first-page":"10734","DOI":"10.1021\/acs.est.5c00906","article-title":"Perfluoroalkane\nSulfonamides and Derivatives, a Different\nClass of PFAS: Sorption and Microbial Biotransformation Insights","volume":"59","author":"Ma","year":"2025","journal-title":"Environ. Sci. Technol."},{"issue":"44","key":"2026091511105036600_cit30","doi-asserted-by":"publisher","first-page":"9380","DOI":"10.1021\/jp034688o","article-title":"First Principles\nCalculations of Aqueous pKa Values for\nOrganic and Inorganic Acids Using COSMO-RS Reveal an Inconsistency\nin the Slope of the pKa Scale","volume":"107","author":"Klamt","year":"2003","journal-title":"J. Phys. Chem.\nA"},{"key":"2026091511105036600_cit31","doi-asserted-by":"publisher","first-page":"1238","DOI":"10.1021\/acs.estlett.5c00688","article-title":"Experimental Determination of pKa for 10 PFAS, Mono-, Di-, and Trifluoroacetic\nAcid by 19F-NMR","volume":"12","author":"Balasuryia","year":"2025","journal-title":"Environ. Sci. Technol.\nLett."},{"key":"2026091511105036600_cit32","doi-asserted-by":"publisher","first-page":"4615","DOI":"10.1021\/acsestwater.4c00631","article-title":"Experimentally Determined\nAqueous Diffusion Coefficients\nof PFAS Using 19F NMR Diffusion-Ordered Spectroscopy","volume":"4","author":"Gauthier","year":"2024","journal-title":"ACS ES&T Water"},{"issue":"23","key":"2026091511105036600_cit33","doi-asserted-by":"publisher","first-page":"8760","DOI":"10.1021\/acs.est.3c01220","article-title":"Identifying Unknown\nFluorine-Containing Compounds in\nEnvironmental Samples Using 19F NMR and Spectral Database\nMatching","volume":"57","author":"Mabury","year":"2023","journal-title":"Environ. Sci. Technol."},{"issue":"7","key":"2026091511105036600_cit34","doi-asserted-by":"publisher","first-page":"510","DOI":"10.1021\/ed050p510","article-title":"Experimental Determination of pKa Values by Use of NMR Chemical-Shifts","volume":"50","author":"Handloser","year":"1973","journal-title":"J. Chem. Educ."},{"key":"2026091511105036600_cit35","doi-asserted-by":"publisher","first-page":"383","DOI":"10.1021\/acs.jpclett.7b02668","article-title":"15N Direct-Detect NMR Spectroscopy Experiments to Examine Determinants\nof Anomalous pKa Values of Lys Residues in Hydrophobic Environments","volume":"9","author":"Kougentakis","year":"2018","journal-title":"J. Phys. Chem. Lett."},{"issue":"3","key":"2026091511105036600_cit36","doi-asserted-by":"publisher","first-page":"29","DOI":"10.3390\/magnetochemistry3030029","article-title":"Low field nmr determination\nof pKa values for hydrophilic drugs for students in medicinal chemistry","volume":"3","author":"Zivkovic","year":"2017","journal-title":"Magnetochemistry"},{"issue":"6","key":"2026091511105036600_cit37","doi-asserted-by":"publisher","DOI":"10.1002\/poc.3940","article-title":"Determination of pKa values of fluorocompounds\nin water using 19F NMR","volume":"32","author":"Parman","year":"2019","journal-title":"J. Phys.\nOrg. Chem."},{"key":"2026091511105036600_cit38","doi-asserted-by":"publisher","first-page":"ACI.S12304","DOI":"10.4137\/aci.S12304","article-title":"Development\nof Methods for the Determination of pKa Values","volume":"8","author":"Reijenga","year":"2013","journal-title":"Anal. Chem. Insights"},{"key":"2026091511105036600_cit39","doi-asserted-by":"publisher","first-page":"100130","DOI":"10.1016\/j.hazadv.2022.100130","article-title":"Adsorption of per-\nand polyfluoroalkyl substances (PFAS) to containers","volume":"7","author":"Zenobio","year":"2022","journal-title":"J. Hazard. Mater. Adv."},{"issue":"5","key":"2026091511105036600_cit40","doi-asserted-by":"publisher","first-page":"2623","DOI":"10.1021\/ac504692m","article-title":"Unified pH Values of\nLiquid Chromatography Mobile Phases","volume":"87","author":"Suu","year":"2015","journal-title":"Anal. Chem."},{"key":"2026091511105036600_cit41","doi-asserted-by":"publisher","first-page":"117203","DOI":"10.1016\/j.bmc.2023.117203","article-title":"Ionization\nand lipophilicity in nonpolar media mimicking the cell membrane interior","volume":"81","author":"Vallaro","year":"2023","journal-title":"Bioorg. Med. Chem."},{"key":"2026091511105036600_cit42","doi-asserted-by":"publisher","first-page":"462795","DOI":"10.1016\/j.chroma.2021.462795","article-title":"Determination\nof the aqueous pKa of very insoluble drugs\nby capillary electrophoresis: Internal standards for methanol-water\nextrapolation","volume":"1665","author":"Albishri","year":"2022","journal-title":"J. Chromatogr. A"},{"issue":"20","key":"2026091511105036600_cit43","doi-asserted-by":"publisher","first-page":"1355","DOI":"10.1002\/jcc.26939","article-title":"Computational protocol\nfor predicting 19F NMR chemical shifts for PFAS and connection\nto PFAS structure","volume":"43","author":"Mifkovic","year":"2022","journal-title":"J. Comput. Chem."},{"issue":"3","key":"2026091511105036600_cit44","doi-asserted-by":"publisher","first-page":"277","DOI":"10.1007\/BF00197809","article-title":"NMRPipe: a multidimensional spectral\nprocessing system based on UNIX\npipes","volume":"6","author":"Delaglio","year":"1995","journal-title":"J. Biomol. NMR"},{"key":"2026091511105036600_cit45","unstructured":"A Python library of algorithms for the baseline correction of experimental\ndata; (accessed Jan 19, 2025)."},{"key":"2026091511105036600_cit46","unstructured":"MATLAB, Version: 9. 13. 0; The MathWorks\nInc.: Natick, Massachusetts, United\nStates, 2022."},{"key":"2026091511105036600_cit47","unstructured":"Visual MINTEQ 4.0. https:\/\/vminteq.com\/download\/ (accessed Mar 20, 2025)."},{"issue":"3","key":"2026091511105036600_cit48","doi-asserted-by":"publisher","first-page":"1103","DOI":"10.1021\/je700055p","article-title":"Static Dielectric Constants\nof Acetonitrile\/Water Mixtures at Different\nTemperatures and Debye-Hu\u0308ckel A and a0B Parameters for Activity\nCoefficients","volume":"52","author":"Gagliardi","year":"2007","journal-title":"J. Chem. Eng. 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