{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,27]],"date-time":"2026-09-27T05:07:04Z","timestamp":1790485624653,"version":"4.1.0"},"reference-count":52,"publisher":"American Chemical Society (ACS)","issue":"11","license":[{"start":{"date-parts":[[2021,3,9]],"date-time":"2021-03-09T00:00:00Z","timestamp":1615248000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001665","name":"Agence Nationale de la Recherche","doi-asserted-by":"publisher","award":["ANR-11-IDEX-0003-02"],"award-info":[{"award-number":["ANR-11-IDEX-0003-02"]}],"id":[{"id":"10.13039\/501100001665","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004794","name":"Centre National de la Recherche Scientifique","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100004794","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100006489","name":"Commissariat \u00e0 l'\u00c9nergie Atomique et aux \u00c9nergies Alternatives","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100006489","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2021,3,23]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Microbiological reductive sulfidation (RS) has rarely been documented, although it represents an efficient strategy for thiol formation. In this work, we reported on the sulfate-respiring bacterium Desulfovibrio sp.86 that has previously demonstrated RS activity toward the pesticide chlordecone. The purpose of this study was to assess its substrate versatility using a set of 28 carbonyls, to compare with chemical RS and to rationalize the observed trends using a dual experimental and theoretical approach. The chemical RS generally proceeds in two steps (S\/O exchange using a sulfur donor like P4S10, reduction of the thione intermediate). Intriguingly, chlordecone was found to be converted into chlordecthiol following the first step. Hence, we designed a protocol and applied it to the 28 substrates to assess their propensity to be directly converted into thiols with the P4S10 treatment alone. Finally, we performed density functional theory calculations on these carbonyls and their thiocarbonyl derivatives to build a set of structural, electronic, and thermodynamic parameters. The results showed that chemical and microbiological RS probably involved two distinct mechanisms. Chemically, we observed that several carbonyls, possessing electron-withdrawing groups and\/or aromatic rings, were directly transformed into thiols in the presence of P4S10. The correlation obtained with the electron affinity of the thiones led us to conclude that a probable single-electron reductive transfer occurred during the first step. We also found that Desulfovibrio sp.86 transformed a variety of aldehydes and ketones, without ever detecting thiones. No significant correlation was observed with the calculated parameters, but a relationship between aldehyde RS biotransformation and bacterial growth was observed. Differences in selectivity with chemical RS open the way for further applications in organic synthesis.<\/jats:p>","DOI":"10.1021\/acsomega.0c06041","type":"journal-article","created":{"date-parts":[[2021,3,9]],"date-time":"2021-03-09T16:13:23Z","timestamp":1615306403000},"page":"7512-7523","source":"Crossref","is-referenced-by-count":5,"title":["Microbiological versus Chemical Reductive Sulfidation:\nAn Experimental and Theoretical Study"],"prefix":"10.1021","volume":"6","author":[{"given":"Oriane","family":"Della-Negra","sequence":"first","affiliation":[{"name":"Ge\u0301nomique Me\u0301tabolique, Genoscope, Institut Franc\u0327ois Jacob, CEA, CNRS, Univ Evry, Universite\u0301 Paris-Saclay , ,","place":["Evry, France, 91057"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Brieuc","family":"Le Cacher de Bonneville","sequence":"additional","affiliation":[{"name":"Ge\u0301nomique Me\u0301tabolique, Genoscope, Institut Franc\u0327ois Jacob, CEA, CNRS, Univ Evry, Universite\u0301 Paris-Saclay , ,","place":["Evry, France, 91057"]},{"name":"Laboratoire de Chimie Mole\u0301culaire, Ecole Polytechnique, CNRS, IP Paris , ,","place":["Palaiseau, France, 91128"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Se\u0301bastien","family":"Chaussonnerie","sequence":"additional","affiliation":[{"name":"Ge\u0301nomique Me\u0301tabolique, Genoscope, Institut Franc\u0327ois Jacob, CEA, CNRS, Univ Evry, Universite\u0301 Paris-Saclay , ,","place":["Evry, France, 91057"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4335-9956","authenticated-orcid":true,"given":"Denis","family":"Le Paslier","sequence":"additional","affiliation":[{"name":"Ge\u0301nomique Me\u0301tabolique, Genoscope, Institut Franc\u0327ois Jacob, CEA, CNRS, Univ Evry, Universite\u0301 Paris-Saclay , ,","place":["Evry, France, 91057"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5677-3569","authenticated-orcid":true,"given":"Gilles","family":"Frison","sequence":"additional","affiliation":[{"name":"Laboratoire de Chimie Mole\u0301culaire, Ecole Polytechnique, CNRS, IP Paris , ,","place":["Palaiseau, France, 91128"]},{"name":"Sorbonne Universite\u0301, CNRS, Laboratoire de Chimie The\u0301orique , ,","place":["Paris, France, 75005"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3028-4764","authenticated-orcid":true,"given":"Pierre-Loi\u0308c","family":"Saaidi","sequence":"additional","affiliation":[{"name":"Ge\u0301nomique Me\u0301tabolique, Genoscope, Institut Franc\u0327ois Jacob, CEA, CNRS, Univ Evry, Universite\u0301 Paris-Saclay , ,","place":["Evry, France, 91057"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2021,3,9]]},"reference":[{"key":"2026081415094094200_cit1","doi-asserted-by":"publisher","first-page":"194","DOI":"10.1080\/00304940509354887","article-title":"Reductive\nThiolation Approach to Pure Cyclobutyl Phenyl\nSulfide","volume":"37","author":"Fyfe","year":"2005","journal-title":"Org. Prep. Proced. Int."},{"key":"2026081415094094200_cit2","doi-asserted-by":"publisher","first-page":"102","DOI":"10.1246\/cl.151035","article-title":"Emerging Organosulfonium Electrophiles\nas Unique Reagents\nfor Carbon\u2013Sulfur Bond Formation: Prospects in Synthetic Chemistry\nof Organosulfur Compounds","volume":"45","author":"Aida","year":"2016","journal-title":"Chem. Lett."},{"key":"2026081415094094200_cit3","doi-asserted-by":"publisher","first-page":"11287","DOI":"10.1002\/anie.201605193","article-title":"Cobalt-Catalyzed C\u2013H Thiolation\nthrough Dehydrogenative Cross-Coupling","volume":"55","author":"Gensch","year":"2016","journal-title":"Angew.\nChem., Int. Ed."},{"key":"2026081415094094200_cit4","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-018-04646-2","article-title":"Nickel-catalyzed\nreductive thiolation and selenylation of unactivated alkyl bromides","volume":"9","author":"Fang","year":"2018","journal-title":"Nat. Commun."},{"key":"2026081415094094200_cit5","doi-asserted-by":"publisher","first-page":"1066","DOI":"10.1002\/adsc.201601329","article-title":"Recent\nAdvances in Organic Reactions Involving Elemental Sulfur","volume":"359","author":"Nguyen","year":"2017","journal-title":"Adv. Synth. Catal."},{"key":"2026081415094094200_cit6","doi-asserted-by":"publisher","DOI":"10.1007\/s41061-018-0209-0","article-title":"The Construction\nand Application of C\ue5fbS Bonds","volume":"376","author":"Murai","year":"2018","journal-title":"Top. Curr.\nChem."},{"key":"2026081415094094200_cit7","doi-asserted-by":"publisher","first-page":"873","DOI":"10.1016\/0040-4039(93)89036-P","article-title":"Bis\u00ad(trimethylsilyl)\u00adsulfide\nbased thionation of carbonyl\ncompounds: Synthesis of thioketones","volume":"34","author":"Degl\u2019Innocenti","year":"1993","journal-title":"Tetrahedron\nLett."},{"key":"2026081415094094200_cit8","doi-asserted-by":"publisher","first-page":"8433","DOI":"10.1016\/j.tetlet.2006.09.033","article-title":"Preparation and structural\ncharacterization of a new class of stable thioketones: ortho-hydroxythioacetophenones","volume":"47","author":"Nguyen","year":"2006","journal-title":"Tetrahedron Lett."},{"key":"2026081415094094200_cit9","doi-asserted-by":"publisher","first-page":"2890","DOI":"10.1021\/jo7022069","article-title":"Expeditious Microwave-Assisted Thionation\nwith the System PSCl3\/H2O\/Et3N under\nSolvent-Free Condition","volume":"73","author":"Pathak","year":"2008","journal-title":"J. Org. Chem."},{"key":"2026081415094094200_cit10","doi-asserted-by":"publisher","first-page":"3419","DOI":"10.1021\/cr900243d","article-title":"A Berzelius Reagent, Phosphorus Decasulfide\n(P4S10), in Organic Syntheses","volume":"110","author":"Ozturk","year":"2010","journal-title":"Chem. Rev."},{"key":"2026081415094094200_cit11","doi-asserted-by":"publisher","first-page":"2641","DOI":"10.1081\/SCC-200025627","article-title":"Synthesis of Dithioacetals and Oxathioacetals\nwith Chiral Auxiliaries","volume":"34","author":"Zaidi","year":"2004","journal-title":"Synth. Commun."},{"key":"2026081415094094200_cit12","doi-asserted-by":"publisher","first-page":"447","DOI":"10.1016\/S0040-4039(97)10572-X","article-title":"Thioketones as key\nintermediates\nin the reduction of ketones to thiols by HS\u2013 in natural environments","volume":"39","author":"Schneckenburger","year":"1998","journal-title":"Tetrahedron Lett."},{"key":"2026081415094094200_cit13","doi-asserted-by":"publisher","first-page":"354","DOI":"10.1021\/jo01061a021","article-title":"The Reductive Thiolation\nof Fluorinated Carbonyl Compounds","volume":"26","author":"Harris","year":"1961","journal-title":"J. Org. Chem."},{"key":"2026081415094094200_cit14","doi-asserted-by":"publisher","first-page":"694","DOI":"10.5059\/yukigoseikyokaishi.33.694","article-title":"The Reduction of Carbonyl\nCompounds\nwith Hydrogen Sulfide under Pressure","volume":"33","author":"Takido","year":"1975","journal-title":"J. Synth.\nOrg. Chem., Jpn."},{"key":"2026081415094094200_cit15","doi-asserted-by":"publisher","first-page":"1502","DOI":"10.1246\/nikkashi.1987.1502","article-title":"Reductive Thiolation\nof Aromatic Ketones and Aldehyde\nwith Sulfur, Carbon Monoxide and Water Leading to Thiols","volume":"1987","author":"Nishiyama","year":"1987","journal-title":"Nippon Kagaku Kaishi"},{"key":"2026081415094094200_cit16","doi-asserted-by":"publisher","DOI":"10.1038\/s41598-020-70124-9","article-title":"Transformation of the recalcitrant pesticide chlordecone\nby Desulfovibrio sp.86 with a switch from ring-opening dechlorination\nto reductive sulfidation activity","volume":"10","author":"Della-Negra","year":"2020","journal-title":"Sci. Rep."},{"key":"2026081415094094200_cit17","doi-asserted-by":"publisher","first-page":"541","DOI":"10.1016\/S1367-5931(00)00249-0","article-title":"Enzymology\nof carbon\u2013sulfur bond formation","volume":"5","author":"Marquet","year":"2001","journal-title":"Curr.\nOpin. Chem. Biol."},{"key":"2026081415094094200_cit18","doi-asserted-by":"publisher","first-page":"5521","DOI":"10.1021\/acs.chemrev.6b00697","article-title":"Enzymatic Carbon\u2013Sulfur\nBond Formation in Natural Product Biosynthesis","volume":"117","author":"Dunbar","year":"2017","journal-title":"Chem. Rev."},{"key":"2026081415094094200_cit19","doi-asserted-by":"publisher","first-page":"20096","DOI":"10.1074\/jbc.M002680200","article-title":"The iscS Gene\nin Escherichia coli Is Required for\nthe Biosynthesis of 4-Thiouridine, Thiamin, and\nNAD","volume":"275","author":"Lauhon","year":"2000","journal-title":"J. Biol. Chem."},{"key":"2026081415094094200_cit20","doi-asserted-by":"publisher","first-page":"7405","DOI":"10.1021\/ja1014037","article-title":"A Biosynthetic Pathway for BE-7585A,\na 2-Thiosugar-Containing Angucycline-Type Natural Product","volume":"132","author":"Sasaki","year":"2010","journal-title":"J. Am. Chem. Soc."},{"key":"2026081415094094200_cit21","doi-asserted-by":"publisher","first-page":"337","DOI":"10.1007\/s00775-014-1173-y","article-title":"The biosynthesis\nof the molybdenum cofactors","volume":"20","author":"Mendel","year":"2015","journal-title":"J. Biol. Inorg.\nChem."},{"key":"2026081415094094200_cit22","doi-asserted-by":"publisher","first-page":"799","DOI":"10.1002\/cbic.201500670","article-title":"Identifying\nthe Minimal Enzymes for Unusual Carbon\u2013Sulfur Bond Formation\nin Thienodolin Biosynthesis","volume":"17","author":"Wang","year":"2016","journal-title":"ChemBioChem"},{"key":"2026081415094094200_cit23","doi-asserted-by":"publisher","first-page":"1060","DOI":"10.1021\/acs.jnatprod.7b00835","article-title":"Heterologous\nExpression Guides Identification of the Biosynthetic Gene Cluster\nof Chuangxinmycin, an Indole Alkaloid Antibiotic","volume":"81","author":"Xu","year":"2018","journal-title":"J. Nat. Prod."},{"key":"2026081415094094200_cit24","doi-asserted-by":"crossref","unstructured":"Lesueur-Jannoyer, M.; Cattan, P.; Woignier, T.; Clostre, F.\n          Crisis Management\nof Chronic Pollution: Contaminated Soil and Human Health. CRC Press; 2016. https:\/\/www.routledge.com\/Crisis-Management-of-Chronic-Pollution-Contaminated-Soil-and-Human-Health\/Jannoyer-Cattan-Woignier-Clostre\/p\/book\/9781498737838 (accessed April 15, 2020).","DOI":"10.1201\/9781315369440"},{"key":"2026081415094094200_cit25","doi-asserted-by":"publisher","first-page":"1278","DOI":"10.1021\/jo01322a020","article-title":"Structures of some Kepone photoproducts and related\nchlorinated pentacyclodecanes by carbon-13 and proton nuclear magnetic\nresonance","volume":"44","author":"Wilson","year":"1979","journal-title":"J. Org. Chem."},{"key":"2026081415094094200_cit26","doi-asserted-by":"publisher","first-page":"111","DOI":"10.1021\/jf60144a004","article-title":"Formation and Evaluation\nof Derivatives, Preparation and Insecticidal Evaluation of Alcoholic\nAnalogs of Kepone","volume":"14","author":"Gilbert","year":"1966","journal-title":"J. Agric. Food Chem."},{"key":"2026081415094094200_cit27","doi-asserted-by":"publisher","first-page":"115","DOI":"10.1021\/jf60144a005","article-title":"Formation and Evaluation\nof Derivatives,\nPreparation and Insecticidal Evaluation of Alcohol and Amine Adducts\nof Kepone","volume":"14","author":"Gilbert","year":"1966","journal-title":"J. Agric. Food Chem."},{"key":"2026081415094094200_cit28","doi-asserted-by":"publisher","first-page":"232","DOI":"10.1002\/bms.1200050312","article-title":"Mass spectrometric analyses and characterization of\nKepone in environmental and human samples","volume":"5","author":"Harless","year":"1978","journal-title":"Biol.\nMass Spectrom."},{"key":"2026081415094094200_cit29","doi-asserted-by":"publisher","first-page":"18","DOI":"10.1016\/j.chemosphere.2016.05.018","article-title":"Toward better\nunderstanding of chloral hydrate stability\nin water: Kinetics, pathways, and influencing factors","volume":"157","author":"Ma","year":"2016","journal-title":"Chemosphere"},{"key":"2026081415094094200_cit30","doi-asserted-by":"publisher","first-page":"1546","DOI":"10.1021\/jo101865y","article-title":"Thionations Using\na P4S10\u2013Pyridine Complex in Solvents Such as Acetonitrile and\nDimethyl Sulfone","volume":"76","author":"Bergman","year":"2011","journal-title":"J. Org. Chem."},{"key":"2026081415094094200_cit31","doi-asserted-by":"publisher","first-page":"431","DOI":"10.1021\/ef00034a012","article-title":"Aqueous high-temperature chemistry\nof carbo- and heterocycles. 17. Thiophene, tetrahydrothiophene, 2-methylthiophene,\n2,5-dimethylthiophene, benzo\u00ad[b]\u00adthiophene, and dibenzothiophene","volume":"6","author":"Katritzky","year":"1992","journal-title":"Energy Fuels"},{"key":"2026081415094094200_cit32","first-page":"95","article-title":"Chapter Three - Paal\u2013Knorr Reaction in the\nSynthesis of Heterocyclic\nCompounds","volume-title":"Advances in Heterocyclic Chemistry","author":"Khaghaninejad","year":"2014"},{"key":"2026081415094094200_cit33","doi-asserted-by":"publisher","DOI":"10.3390\/pr8030275","article-title":"Mass\nSpectroscopic Analysis, MNDO Quantum Chemical Studies and Antifungal\nActivity of Essential and Recovered Oil Constituents of Lemon-Scented\nGum against Three Common Molds","volume":"8","author":"Behiry","year":"2020","journal-title":"Processes"},{"key":"2026081415094094200_cit34","doi-asserted-by":"publisher","first-page":"801","DOI":"10.1021\/jf00118a030","article-title":"Deterioration mechanism\nof lemon flavor. 2. Formation mechanism of off-odor substances arising\nfrom citral","volume":"31","author":"Kimura","year":"1983","journal-title":"J. Agric. Food Chem."},{"key":"2026081415094094200_cit35","doi-asserted-by":"publisher","first-page":"176","DOI":"10.1016\/j.jfda.2015.02.001","article-title":"Reactivity and stability\nof selected flavor compounds","volume":"23","author":"Weerawatanakorn","year":"2015","journal-title":"J. Food Drug Anal."},{"key":"2026081415094094200_cit36","doi-asserted-by":"publisher","first-page":"4364","DOI":"10.1002\/cctc.201700734","article-title":"Selectivity\nin the Cyclization of Citronellal Introduced by Squalene Hopene Cyclase\nVariants","volume":"9","author":"Bastian","year":"2017","journal-title":"ChemCatChem"},{"key":"2026081415094094200_cit37","doi-asserted-by":"publisher","first-page":"2164","DOI":"10.1016\/j.tetlet.2010.02.081","article-title":"Flavouring and odorant thiols from renewable natural\nresources by InIII-catalysed hydrothioacetylation and lipase-catalysed\nsolvolysis","volume":"51","author":"Dia","year":"2010","journal-title":"Tetrahedron Lett."},{"key":"2026081415094094200_cit38","doi-asserted-by":"publisher","first-page":"505","DOI":"10.1007\/BF00900973","article-title":"Zur Kenntnis des 1-Thiophthalids","volume":"89","author":"Prey","year":"1958","journal-title":"Monatsh. Chem. Verw. Teile Anderer Wiss."},{"key":"2026081415094094200_cit39","doi-asserted-by":"publisher","first-page":"355","DOI":"10.1007\/BF00276531","article-title":"Anaerobic degradation of acetone\nby Desulfococcus biacutus spec. nov","volume":"154","author":"Platen","year":"1990","journal-title":"Arch. Microbiol."},{"key":"2026081415094094200_cit40","doi-asserted-by":"publisher","first-page":"11559","DOI":"10.1021\/bi00094a012","article-title":"Aldehyde\noxidoreductase activity\nin Desulfovibrio gigas: In vitro reconstitution of an electron-transfer\nchain from aldehydes to the production of molecular hydrogen","volume":"32","author":"Barata","year":"1993","journal-title":"Biochemistry"},{"key":"2026081415094094200_cit41","doi-asserted-by":"publisher","first-page":"135","DOI":"10.1111\/j.1365-313X.2004.02113.x","article-title":"Metabolic\nengineering of monoterpene biosynthesis: two-step production of (+)-trans-isopiperitenol\nby tobacco","volume":"39","author":"Lu\u0308cker","year":"2004","journal-title":"Plant J."},{"key":"2026081415094094200_cit42","doi-asserted-by":"publisher","first-page":"11423","DOI":"10.1021\/jp907209a","article-title":"Computational\nCalculation of Equilibrium\nConstants: Addition to Carbonyl Compounds","volume":"113","author":"Go\u0301mez-Bombarelli","year":"2009","journal-title":"J.\nPhys. Chem. A"},{"key":"2026081415094094200_cit43","first-page":"1","article-title":"The Reversible\nHydration of Carbonyl Compounds","volume-title":"Advances\nin Physical Organic Chemistry","author":"Bell","year":"1966"},{"key":"2026081415094094200_cit44","doi-asserted-by":"publisher","first-page":"3524","DOI":"10.1021\/ja00990a032","article-title":"Hydration\nof acetaldehyde. I. Equilibrium thermodynamic parameters","volume":"89","author":"Kurz","year":"1967","journal-title":"J. Am. Chem. Soc."},{"key":"2026081415094094200_cit45","unstructured":"Dawson, G. W.; Weimer, W. C.; Shupe, S. J.\n          Kepone--a case\nstudy of a persistent material. Water - Am.\nInst. Chem. Eng., 1979. http:\/\/agris.fao.org\/agris-search\/search.do?recordID=US201301357524 (accessed April 10, 2020)."},{"key":"2026081415094094200_cit46","doi-asserted-by":"publisher","first-page":"6133","DOI":"10.1021\/acs.est.8b06305","article-title":"Natural Chlordecone Degradation Revealed by\nNumerous Transformation Products Characterized in Key French West\nIndies Environmental Compartments","volume":"53","author":"Chevallier","year":"2019","journal-title":"Environ.\nSci. Technol."},{"key":"2026081415094094200_cit47","doi-asserted-by":"publisher","first-page":"3865","DOI":"10.1103\/PhysRevLett.77.3865","article-title":"Generalized\nGradient Approximation\nMade Simple","volume":"77","author":"Perdew","year":"1996","journal-title":"Phys. Rev. Lett."},{"key":"2026081415094094200_cit48","doi-asserted-by":"publisher","first-page":"1396","DOI":"10.1103\/PhysRevLett.78.1396","article-title":"Generalized\nGradient Approximation\nMade Simple [Phys. Rev. Lett. 77, 3865 (1996)]","volume":"78","author":"Perdew","year":"1997","journal-title":"Phys. Rev. Lett."},{"key":"2026081415094094200_cit49","doi-asserted-by":"publisher","first-page":"215","DOI":"10.1007\/s00214-007-0310-x","article-title":"The M06 suite of\ndensity functionals for main group\nthermochemistry, thermochemical kinetics, noncovalent interactions,\nexcited states, and transition elements: two new functionals and systematic\ntesting of four M06-class functionals and 12 other functionals","volume":"120","author":"Zhao","year":"2008","journal-title":"Theor. Chem. Acc."},{"key":"2026081415094094200_cit50","doi-asserted-by":"publisher","first-page":"1426","DOI":"10.1021\/jz2004792","article-title":"Ground Electronic State\nof Peptide Cation Radicals: A Delocalized Unpaired Electron?","volume":"2","author":"Gilson","year":"2011","journal-title":"J. Phys. Chem. Lett."},{"key":"2026081415094094200_cit51","doi-asserted-by":"publisher","first-page":"367","DOI":"10.32614\/RJ-2016-027","article-title":"Nonparametric\nTests for the Interaction in Two-way Factorial Designs Using R","volume":"8","author":"Feys","year":"2016","journal-title":"R J."},{"key":"2026081415094094200_cit52","unstructured":"Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Menucci, B.; Petersson, G. A.; \n               et al.\n          Gaussian\n09.Gaussian, Inc.: Wallingford, CT, 2013."}],"container-title":["ACS Omega"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acsomega.0c06041","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/acsodf\/article-pdf\/6\/11\/7512\/3728740\/ao0c06041.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/acsodf\/article-pdf\/6\/11\/7512\/3728740\/ao0c06041.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,8,14]],"date-time":"2026-08-14T19:25:27Z","timestamp":1786735527000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/acsodf\/article\/6\/11\/7512\/384702\/Microbiological-versus-Chemical-Reductive"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,3,9]]},"references-count":52,"journal-issue":{"issue":"11","published-online":{"date-parts":[[2021,3,9]]},"published-print":{"date-parts":[[2021,3,23]]}},"URL":"https:\/\/doi.org\/10.1021\/acsomega.0c06041","relation":{},"ISSN":["2470-1343"],"issn-type":[{"value":"2470-1343","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,3,9]]}}}