{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,21]],"date-time":"2026-08-21T13:09:49Z","timestamp":1787317789296,"version":"build-2736575974"},"reference-count":68,"publisher":"Wiley","issue":"15","license":[{"start":{"date-parts":[[2022,4,22]],"date-time":"2022-04-22T00:00:00Z","timestamp":1650585600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["Germany's Excellence Strategy \u2010 EXC 2033 \u2010 3906778"],"award-info":[{"award-number":["Germany's Excellence Strategy \u2010 EXC 2033 \u2010 3906778"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["Project Ha 2588\/8\u20101"],"award-info":[{"award-number":["Project Ha 2588\/8\u20101"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["J Comput Chem"],"published-print":{"date-parts":[[2022,6,5]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    In this contribution we extent the use of the conductor\u2010like screening model for realistic solvation (COSMO\u2010RS) to the prediction of p\n                    <jats:italic>K<\/jats:italic>\n                    <jats:sub>a<\/jats:sub>\n                    values in acetone, a commonly used dipolar aprotic solvent. For this, we calculated the Gibbs free energy of dissociation of 120 organic acids (nine acrylic acids, 87 benzoic acids, nine phenols, and 15 benzenesulfonamides) using COSMO\u2010RS at the two levels BP\u2010TZVP and BP\u2010TZVPD\u2010FINE and determined the parameters for a linear free energy relation for the  prediction by performing linear fits to experimental values. Our results suggest that the data set dissects into two groups, with the phenols being different from the other three subsets. The acrylic and benzoic acids and the sulfonamides can be treated together and yield an excellent linear correlation () with an RMSD of only ~0.3. The slope is found to be significantly smaller than the theoretical value (), only 45% of it, which is in accordance with findings in the literature. The phenols, however, while similarly well correlated in their own subset with an RMSD of 1.7\u20131.9, exhibit a slope larger than one. We discuss both a higher uncertainty in the reference values as well as physical origins as possible reasons.\n                  <\/jats:p>","DOI":"10.1002\/jcc.26864","type":"journal-article","created":{"date-parts":[[2022,4,23]],"date-time":"2022-04-23T02:25:18Z","timestamp":1650680718000},"page":"1011-1022","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":11,"title":["Prediction of acid p\n                    <i>K<\/i>\n                    <sub>a<\/sub>\n                    values in the solvent acetone based on COSMO\u2010RS"],"prefix":"10.1002","volume":"43","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-8734-5807","authenticated-orcid":false,"given":"Niklas","family":"S\u00fclzner","sequence":"first","affiliation":[{"name":"Lehrstuhl f\u00fcr Theoretische Chemie Ruhr\u2010Universit\u00e4t Bochum  Bochum 44780 Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0100-1959","authenticated-orcid":false,"given":"Julia","family":"Haberhauer","sequence":"additional","affiliation":[{"name":"Lehrstuhl f\u00fcr Theoretische Chemie Ruhr\u2010Universit\u00e4t Bochum  Bochum 44780 Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5752-2710","authenticated-orcid":false,"given":"Christof","family":"H\u00e4ttig","sequence":"additional","affiliation":[{"name":"Lehrstuhl f\u00fcr Theoretische Chemie Ruhr\u2010Universit\u00e4t Bochum  Bochum 44780 Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9508-4889","authenticated-orcid":false,"given":"Arnim","family":"Hellweg","sequence":"additional","affiliation":[{"name":"Dassault Syst\u00e8mes Deutschland GmbH  Am Kabellager 11\u201015, K\u00f6ln 51063 Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2022,4,22]]},"reference":[{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jpcb.1c01929"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8OB00473K"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.6b03182"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jclepro.2020.121446"},{"key":"e_1_2_7_6_1","volume-title":"Proton\u2010Transfer Reactions","author":"Caldin E. F.","year":"2013"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.4137\/ACI.S12304"},{"key":"e_1_2_7_8_1","first-page":"26","volume":"6","author":"Pathare B.","year":"2014","journal-title":"Int. J. Pharm. Pharm. Sci."},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/ed080p822"},{"key":"e_1_2_7_10_1","first-page":"243","volume":"60","author":"Buv\u00e1ri\u2010Barcza \u00c1.","year":"2005","journal-title":"Pharmazie"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.aca.2006.03.020"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/S1574-1400(10)06008-1"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/wcms.1218"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1002\/wcms.1086"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr9904009"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1039\/P29930000799"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1039\/b000184h"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.1002\/wcms.56"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0009-2614(02)01686-X"},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.1002\/qua.24699"},{"key":"e_1_2_7_21_1","doi-asserted-by":"publisher","DOI":"10.1021\/j100007a062"},{"key":"e_1_2_7_22_1","first-page":"5074","volume":"102","author":"Klamt A.","year":"1998","journal-title":"Chem. A Eur. J."},{"key":"e_1_2_7_23_1","doi-asserted-by":"publisher","DOI":"10.1002\/aic.690480220"},{"key":"e_1_2_7_24_1","doi-asserted-by":"publisher","DOI":"10.1146\/annurev-chembioeng-073009-100903"},{"key":"e_1_2_7_25_1","first-page":"9380","volume":"107","author":"Klamt A.","year":"2003","journal-title":"Chem. A Eur. J."},{"key":"e_1_2_7_26_1","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.20309"},{"key":"e_1_2_7_27_1","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.21103"},{"key":"e_1_2_7_28_1","unstructured":"BIOVIA COSMOtherm Release2020;Dassault Syst\u00e8mes.http:\/\/www.3ds.com."},{"key":"e_1_2_7_29_1","volume-title":"Acid\u2010base dissociation constants in dipolar aprotic solvents, 1st edn","author":"Izutsu K.","year":"1990"},{"key":"e_1_2_7_30_1","doi-asserted-by":"publisher","DOI":"10.1007\/s10822-014-9764-9"},{"key":"e_1_2_7_31_1","doi-asserted-by":"publisher","DOI":"10.1135\/cccc19862135"},{"key":"e_1_2_7_32_1","doi-asserted-by":"publisher","DOI":"10.1135\/cccc19942005"},{"key":"e_1_2_7_33_1","doi-asserted-by":"publisher","DOI":"10.1135\/cccc19970913"},{"key":"e_1_2_7_34_1","doi-asserted-by":"publisher","DOI":"10.1135\/cccc19940627"},{"key":"e_1_2_7_35_1","doi-asserted-by":"publisher","DOI":"10.1135\/cccc19941637"},{"key":"e_1_2_7_36_1","unstructured":"J.Knorr N.S\u00fclzner B.Geissler C.Spies A.Grandjean R. J.Kutta G.Jung andP.Nuernberger2022.In Press."},{"key":"e_1_2_7_37_1","unstructured":"N.S\u00fclzner B.Geissler A.Grandjean G.Jung andP.Nuernberger(2022) https:\/\/doi.org\/10.1002\/cptc.202200041R2"},{"key":"e_1_2_7_38_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8CP00643A"},{"key":"e_1_2_7_39_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jctc.0c00316"},{"key":"e_1_2_7_40_1","doi-asserted-by":"publisher","DOI":"10.1002\/aic.15716"},{"key":"e_1_2_7_41_1","doi-asserted-by":"publisher","DOI":"10.1016\/0009-2614(95)00621-A"},{"key":"e_1_2_7_42_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.469408"},{"key":"e_1_2_7_43_1","unstructured":"TURBOMOLE V7.3 A development of University of Karlsruhe and Forschungszentrum Karlsruhe GmbH 1989\u20132007 TURBOMOLE GmbH 2007 2018;http:\/\/www.turbomole.com."},{"key":"e_1_2_7_44_1","unstructured":"BIOVIA COSMOconf Release 2020; Dassault Syst\u00e8mes.http:\/\/www.3ds.com.25"},{"key":"e_1_2_7_45_1","doi-asserted-by":"publisher","DOI":"10.1103\/PhysRevA.38.3098"},{"key":"e_1_2_7_46_1","doi-asserted-by":"publisher","DOI":"10.1103\/PhysRevB.33.8822"},{"key":"e_1_2_7_47_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.467146"},{"key":"e_1_2_7_48_1","doi-asserted-by":"publisher","DOI":"10.1007\/s002140050244"},{"key":"e_1_2_7_49_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.3484283"},{"key":"e_1_2_7_50_1","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.25342"},{"key":"e_1_2_7_51_1","unstructured":"N.S\u00fclzner J.Haberhauer C.H\u00e4ttig andA.Hellweg Raw Data to \"Prediction of acid pKa values in the solvent acetone based on COSMO\u2010RS\"(2022) https:\/\/doi.org\/10.5281\/zenodo.5676011."},{"key":"e_1_2_7_52_1","first-page":"1327","volume":"106","author":"Klici\u0107 J. J.","year":"2002","journal-title":"Chem. A Eur. J."},{"key":"e_1_2_7_53_1","first-page":"8757","volume":"106","author":"Himo F.","year":"2002","journal-title":"Chem. A Eur. J."},{"key":"e_1_2_7_54_1","doi-asserted-by":"publisher","DOI":"10.2478\/acs-2013-0011"},{"key":"e_1_2_7_55_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.theochem.2010.04.002"},{"key":"e_1_2_7_56_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.480486"},{"key":"e_1_2_7_57_1","first-page":"1304","volume":"47","author":"Barabanov V. P.","year":"1973","journal-title":"Russ. J. Phys. Chem."},{"key":"e_1_2_7_58_1","first-page":"2407","volume":"55","author":"Nowak B.","year":"1981","journal-title":"Pol. J. Chem."},{"key":"e_1_2_7_59_1","doi-asserted-by":"publisher","DOI":"10.1135\/cccc19861948"},{"key":"e_1_2_7_60_1","doi-asserted-by":"publisher","DOI":"10.1135\/cccc19780095"},{"key":"e_1_2_7_61_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo060031y"},{"key":"e_1_2_7_62_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.202001649"},{"key":"e_1_2_7_63_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja012474j"},{"key":"e_1_2_7_64_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja010534f"},{"key":"e_1_2_7_65_1","doi-asserted-by":"publisher","DOI":"10.1039\/tf9534900314"},{"key":"e_1_2_7_66_1","first-page":"7413","volume":"106","author":"Chipman D. M.","year":"2002","journal-title":"Chem. A Eur. J."},{"key":"e_1_2_7_67_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr00032a005"},{"key":"e_1_2_7_68_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00165a018"},{"key":"e_1_2_7_69_1","doi-asserted-by":"publisher","DOI":"10.1039\/c3cp53082e"}],"container-title":["Journal of Computational Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/jcc.26864","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/jcc.26864","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/jcc.26864","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,8,25]],"date-time":"2023-08-25T17:38:40Z","timestamp":1692985120000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/jcc.26864"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,4,22]]},"references-count":68,"journal-issue":{"issue":"15","published-print":{"date-parts":[[2022,6,5]]}},"alternative-id":["10.1002\/jcc.26864"],"URL":"https:\/\/doi.org\/10.1002\/jcc.26864","archive":["Portico"],"relation":{},"ISSN":["0192-8651","1096-987X"],"issn-type":[{"value":"0192-8651","type":"print"},{"value":"1096-987X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,4,22]]},"assertion":[{"value":"2021-12-02","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2022-03-29","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2022-04-22","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}