{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,13]],"date-time":"2026-10-13T00:22:15Z","timestamp":1791850935924,"version":"4.3.4"},"reference-count":47,"publisher":"Wiley","issue":"9","license":[{"start":{"date-parts":[[2026,8,19]],"date-time":"2026-08-19T00:00:00Z","timestamp":1787097600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2026,8,19]],"date-time":"2026-08-19T00:00:00Z","timestamp":1787097600000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/501100003593","name":"Conselho Nacional de Desenvolvimento Cient\u00edfico e Tecnol\u00f3gico","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100003593","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002322","name":"Coordena\u00e7\u00e3o de Aperfei\u00e7oamento de Pessoal de N\u00edvel Superior","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100002322","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chirality"],"published-print":{"date-parts":[[2026,9]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    <jats:italic>S<\/jats:italic>\n                    \u2010Naproxen (NPX) exhibits an unusual inversion of its ECD spectrum upon solvent change, a phenomenon that this work analyzes both experimentally and theoretically. By evaluating NPX in water, ethanol, and acetonitrile, it was observed that pH variation shifts the chemical equilibrium between protonated and deprotonated forms, making this transition the direct cause of the ECD signal inversion. Molecular dynamics and TD\u2010DFT (CAM\u2010B3LYP\/aug\u2010cc\u2010pVDZ) calculations corroborated the experimental data, demonstrating that structural changes alter the predominant electronic transitions from \u03c0\u2009\u2192\u2009\u03c0* in NPX to n\u2009\u2192\u2009\u03c0* in the NPX\n                    <jats:sup>\u2212<\/jats:sup>\n                    anion, as evidenced by transition density differences and natural transition orbitals (NTOs). These findings demonstrate that explicit solvent treatment and statistical analysis are requisite to accurately reproduce the data, validating that the negative signal in water and the positive signal in acetonitrile is governed by the predominant species dictated by the chemical equilibrium.\n                  <\/jats:p>","DOI":"10.1002\/chir.70137","type":"journal-article","created":{"date-parts":[[2026,8,19]],"date-time":"2026-08-19T08:06:15Z","timestamp":1787126775000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Evaluating the Solvent and pH Effect in the Inversion of the Circular Dichroism Signal of\n                    <i>S<\/i>\n                    \u2010Naproxen"],"prefix":"10.1002","volume":"38","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-7978-4597","authenticated-orcid":false,"given":"Lucas Chuman","family":"Santana","sequence":"first","affiliation":[{"name":"Department of Physical Chemistry, Institute of Chemistry University of Campinas (UNICAMP)  Campinas SP Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5001-7503","authenticated-orcid":false,"given":"Eduardo","family":"de Faria Franca","sequence":"additional","affiliation":[{"name":"Laboratory of Crystallography and Computational Chemistry, Chemistry Institute Federal University of Uberl\u00e2ndia \u2013 UFU  Uberl\u00e2ndia MG Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2636-3080","authenticated-orcid":false,"given":"Valdecir Farias","family":"Ximenes","sequence":"additional","affiliation":[{"name":"Department of Chemistry, School of Science S\u00e3o Paulo State University (UNESP)  Bauru S\u00e3o Paulo Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2373-267X","authenticated-orcid":false,"given":"Aguinaldo Robinson","family":"de Souza","sequence":"additional","affiliation":[{"name":"Department of Chemistry, School of Science S\u00e3o Paulo State University (UNESP)  Bauru S\u00e3o Paulo Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8349-8179","authenticated-orcid":false,"given":"Nelson Henrique","family":"Morgon","sequence":"additional","affiliation":[{"name":"Department of Physical Chemistry, Institute of Chemistry University of Campinas (UNICAMP)  Campinas SP Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,8,19]]},"reference":[{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/chir.22988"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1080\/00268979709482744"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1039\/b515476f"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4CS00104D"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1038\/nprot.2006.202"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1002\/chir.20265"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1002\/chir.20789"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1002\/chir.20310"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.43.3920"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1515\/9783110867855"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jpba.2006.06.015"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp020124t"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1002\/cphc.200600477"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200702858"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/qua.21043"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0CP04027D"},{"key":"e_1_2_7_18_1","unstructured":"PubChem homepage retrieved January 2025 https:\/\/pubchem.ncbi.nlm.nih.gov\/compound\/Naproxen."},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1039\/c0cp00111b"},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00074a030"},{"key":"e_1_2_7_21_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cpc.2010.04.018"},{"key":"e_1_2_7_22_1","doi-asserted-by":"publisher","DOI":"10.1080\/08927022.2011.608847"},{"key":"e_1_2_7_23_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja9621760"},{"key":"e_1_2_7_24_1","unstructured":"M.Abraham A.Alekseenko B.Andrews et\u00a0al. \u201cGROMACS 2025.0 Manual \u201d Zenodo (2025)."},{"key":"e_1_2_7_25_1","doi-asserted-by":"publisher","DOI":"10.1137\/0916069"},{"key":"e_1_2_7_26_1","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1096-987X(199709)18:12<1463::AID-JCC4>3.0.CO;2-H"},{"key":"e_1_2_7_27_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.464397"},{"key":"e_1_2_7_28_1","doi-asserted-by":"publisher","DOI":"10.1103\/PhysRevLett.45.1196"},{"issue":"7182","key":"e_1_2_7_29_1","first-page":"190","article-title":"Polymorphic Transitions in Single Crystals: A New Molecular Dynamics Method","volume":"52","author":"Parrinello M.","year":"1981","journal-title":"Journal of Applied Physics"},{"key":"e_1_2_7_30_1","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3773(19990115)38:1\/2<236::AID-ANIE236>3.0.CO;2-M"},{"key":"e_1_2_7_31_1","doi-asserted-by":"publisher","DOI":"10.1016\/0263-7855(96)00018-5"},{"key":"e_1_2_7_32_1","unstructured":"PyMol homepage retrieved January 2025 https:\/\/www.pymol.org\/."},{"key":"e_1_2_7_33_1","volume-title":"Gaussian 16, Revision C. 01","author":"Frisch M. J.","year":"2016"},{"key":"e_1_2_7_34_1","volume-title":"Gauss View, Version 5","author":"Dennington R.","year":"2009"},{"key":"e_1_2_7_35_1","doi-asserted-by":"publisher","DOI":"10.1103\/PhysRevLett.52.997"},{"key":"e_1_2_7_36_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cplett.2004.06.011"},{"issue":"132","key":"e_1_2_7_37_1","first-page":"1","article-title":"Application of Subsurface Bioreactor for Wastewater Treatment","volume":"2","author":"Dolle K.","year":"2017","journal-title":"International Journal of Earth Sciences"},{"key":"e_1_2_7_38_1","doi-asserted-by":"publisher","DOI":"10.1021\/ac300087z"},{"key":"e_1_2_7_39_1","doi-asserted-by":"publisher","DOI":"10.1002\/poc.2946"},{"key":"e_1_2_7_40_1","doi-asserted-by":"publisher","DOI":"10.1002\/poc.610051107"},{"key":"e_1_2_7_41_1","doi-asserted-by":"publisher","DOI":"10.1139\/v76-398"},{"key":"e_1_2_7_42_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molliq.2016.02.045"},{"key":"e_1_2_7_43_1","doi-asserted-by":"publisher","DOI":"10.1088\/0026-1394\/31\/4\/001"},{"key":"e_1_2_7_44_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jpca.6b12287"},{"key":"e_1_2_7_45_1","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.molliq.2025.128341","article-title":"Therapeutic Potential of Carbon Nitride as a Drug Delivery System for Naproxen and Aspirin: A DFT and MD Simulations","volume":"437","author":"Tariq T.","year":"2025","journal-title":"Journal of Molecular Liquids"},{"key":"e_1_2_7_46_1","doi-asserted-by":"publisher","DOI":"10.1002\/chir.22316"},{"key":"e_1_2_7_47_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11224-017-0911-5"},{"key":"e_1_2_7_48_1","article-title":"Integration of Wallach's Rule Into Intermolecular Charge Transfer: A Visual Strategy for Chiral Purification","volume":"11","author":"Wang W.","year":"2024","journal-title":"Advancement of Science"}],"container-title":["Chirality"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chir.70137","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/chir.70137","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chir.70137","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,15]],"date-time":"2026-09-15T02:17:25Z","timestamp":1789438645000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/chir.70137"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,8,19]]},"references-count":47,"journal-issue":{"issue":"9","published-print":{"date-parts":[[2026,9]]}},"alternative-id":["10.1002\/chir.70137"],"URL":"https:\/\/doi.org\/10.1002\/chir.70137","archive":["Portico"],"relation":{},"ISSN":["0899-0042","1520-636X"],"issn-type":[{"value":"0899-0042","type":"print"},{"value":"1520-636X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,8,19]]},"assertion":[{"value":"2026-06-08","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-08-03","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-08-19","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e70137"}}