{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,15]],"date-time":"2026-09-15T11:07:24Z","timestamp":1789470444464,"version":"build-2803163510"},"reference-count":178,"publisher":"AIP Publishing","issue":"11","funder":[{"DOI":"10.13039\/100007780","name":"Indian Institute of Science","doi-asserted-by":"publisher","award":["IE\/REDA-22-1863"],"award-info":[{"award-number":["IE\/REDA-22-1863"]}],"id":[{"id":"10.13039\/100007780","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["pubs.aip.org"],"crossmark-restriction":true},"short-container-title":[],"published-print":{"date-parts":[[2026,9,21]]},"abstract":"<jats:p>The nucleobase cytosine has been utilized for co-crystallization with three coformers (gallic acid, aspirin, and thiazole-4-carboxylic acid) by the solvent grinding method. The resulting salts CYT-GAL, CYT-SAL, and CYT-TCA were characterized by the single-crystal x-ray diffraction technique. Structural analysis reveals that the salts are stabilized by N\u2013H\u22efO and N\u2013H\u22efN hydrogen bonds (HBs). Protonation of cytosine (N3) leads to the formation of R22(8) ring sets, which violates the Watson\u2013Crick pair formation. Furthermore, all the features of these salts were confirmed by PXRD, TGA, NMR, and FTIR. HOMO\u2013LUMO gaps were benchmarked using 65 DFAs against the HF\/VTZ-F12 HOMO\u2013LUMO gaps because DLPNO-CCSD(T)-F12, such as MP2, retains the HF orbitals and does not alter orbital energies. HOMO\u2013LUMO gaps obtained at this level are the same as the HF\/VTZ-F12 HOMO\u2013LUMO gaps. Range-separated double-hybrid DFAs (RSX-QIDH, SCS-RSX-QIDH, and SOS-RSX-QIDH) showed the best agreement with these gaps. G0W0 calculations using several DFAs and HF starting points were additionally performed to assess their reliability for predicting these gaps. Bonding analysis using quantum theory of atoms in molecules (QTAIM), non-covalent interaction (NCI), natural bond orbital, and molecular electrostatic potential was carried out at the DSD-PBEP86-D3BJ\/def2-TZVP level of theory, validated against seven additional DFAs. QTAIM reveals that CYT-GAL is stabilized by N\u2013H\u22efO intermolecular HBs, CYT-SAL is stabilized by a partially covalent O\u2013H\u22efO intramolecular HB (delocalization index 0.1128), and CYT-TCA is stabilized by weaker van der Waals interactions (C\u22efC, C\u22efN, and S\u22efN). Furthermore, NCI analysis reveals new interactions, including intramolecular HBs of type O\u2013H\u22efO and H\u22efO interactions in CYT-GAL, a new H\u22efO interaction in the case of CYT-SAL, and a new C\u22efC interaction in the case of CYT-TCA.<\/jats:p>","DOI":"10.1063\/5.0335574","type":"journal-article","created":{"date-parts":[[2026,9,15]],"date-time":"2026-09-15T10:58:29Z","timestamp":1789469909000},"update-policy":"https:\/\/doi.org\/10.1063\/aip-crossmark-policy-page","source":"Crossref","is-referenced-by-count":0,"title":["Proton-transfer dictated supramolecular hydrogen bonded architecture in cytosine with substituted carboxylic acid coformers: Experimental and theoretical investigation by density functional approximations, DLPNO-CCSD(T)-F12, and G0W0 calculations"],"prefix":"10.1063","volume":"165","author":[{"ORCID":"https:\/\/orcid.org\/0009-0000-3306-9109","authenticated-orcid":false,"given":"Ranganathan","family":"Sathishkumar","sequence":"first","affiliation":[{"name":"Solid State and Structural Chemistry Unit, Indian Institute of Science 1 , Bangalore 560012,","place":["India"]},{"name":"Inorganic and Physical Chemistry, Indian Institute of Science 2 , Bangalore 560012,","place":["India"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0991-7005","authenticated-orcid":false,"given":"Govinda Prasad","family":"Khanal","sequence":"additional","affiliation":[{"name":"Inorganic and Physical Chemistry, Indian Institute of Science 2 , Bangalore 560012,","place":["India"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7186-1444","authenticated-orcid":false,"given":"Nainamalai","family":"Devarajan","sequence":"additional","affiliation":[{"name":"Solid State and Structural Chemistry Unit, Indian Institute of Science 1 , Bangalore 560012,","place":["India"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0008-4571-8821","authenticated-orcid":false,"given":"Dineshchakravarthy","family":"Senthurpandi","sequence":"additional","affiliation":[{"name":"Inorganic and Physical Chemistry, Indian Institute of Science 2 , Bangalore 560012,","place":["India"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9669-4307","authenticated-orcid":false,"given":"Elangannan","family":"Arunan","sequence":"additional","affiliation":[{"name":"Inorganic and Physical Chemistry, Indian Institute of Science 2 , Bangalore 560012,","place":["India"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1632-2595","authenticated-orcid":false,"given":"Munirathinam","family":"Nethaji","sequence":"additional","affiliation":[{"name":"Inorganic and Physical Chemistry, Indian Institute of Science 2 , Bangalore 560012,","place":["India"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"317","published-online":{"date-parts":[[2026,9,15]]},"reference":[{"issue":"1","key":"2026091506582110200_c1","doi-asserted-by":"publisher","first-page":"88","DOI":"10.1016\/j.ijpharm.2012.11.028","volume":"453","year":"2013","journal-title":"Int. J. Pharm."},{"issue":"5","key":"2026091506582110200_c2","doi-asserted-by":"publisher","first-page":"2147","DOI":"10.1021\/cg3002948","volume":"12","year":"2012","journal-title":"Cryst. Growth Des."},{"key":"2026091506582110200_c3","doi-asserted-by":"publisher","first-page":"136264","DOI":"10.1016\/j.snb.2024.136264","volume":"418","year":"2024","journal-title":"Sens. Actuators, B"},{"issue":"1","key":"2026091506582110200_c4","doi-asserted-by":"publisher","first-page":"0965","DOI":"10.36922\/ijb.0965","volume":"10","year":"2023","journal-title":"Int. J. Bioprinting"},{"issue":"35","key":"2026091506582110200_c5","doi-asserted-by":"publisher","first-page":"2403111","DOI":"10.1002\/adma.202403111","volume":"36","year":"2024","journal-title":"Adv. Mater."},{"key":"2026091506582110200_c6","doi-asserted-by":"publisher","first-page":"122105","DOI":"10.1016\/j.indcrop.2025.122105","volume":"236","year":"2025","journal-title":"Ind. Crops Prod."},{"issue":"6","key":"2026091506582110200_c7","doi-asserted-by":"publisher","first-page":"2950","DOI":"10.1021\/cg900129f","volume":"9","year":"2009","journal-title":"Cryst. Growth Des."},{"issue":"2","key":"2026091506582110200_c8","doi-asserted-by":"publisher","first-page":"1106","DOI":"10.1021\/cg800936d","volume":"9","year":"2009","journal-title":"Cryst. Growth Des."},{"issue":"7","key":"2026091506582110200_c9","doi-asserted-by":"publisher","first-page":"890","DOI":"10.1039\/B400978A","volume":"40","year":"2004","journal-title":"Chem. Commun."},{"issue":"5","key":"2026091506582110200_c10","doi-asserted-by":"publisher","first-page":"990","DOI":"10.1002\/jps.20949","volume":"96","year":"2007","journal-title":"J.\u00a0Pharm. Sci."},{"issue":"8","key":"2026091506582110200_c11","doi-asserted-by":"publisher","first-page":"3376","DOI":"10.1021\/cg801019d","volume":"9","year":"2009","journal-title":"Cryst. Growth Des."},{"issue":"4","key":"2026091506582110200_c12","doi-asserted-by":"publisher","first-page":"478","DOI":"10.1002\/(SICI)1520-6017(200004)89:4&lt;478::AID-JPS5&gt;3.0.CO;2-5","volume":"89","year":"2000","journal-title":"J.\u00a0Pharm. Sci."},{"issue":"3","key":"2026091506582110200_c13","doi-asserted-by":"publisher","first-page":"418","DOI":"10.1039\/B815174A","volume":"11","year":"2009","journal-title":"CrystEngComm"},{"issue":"1","key":"2026091506582110200_c14","doi-asserted-by":"publisher","first-page":"8","DOI":"10.1063\/1.475360","volume":"108","year":"1998","journal-title":"J.\u00a0Chem. Phys."},{"issue":"4\u20136","key":"2026091506582110200_c15","doi-asserted-by":"publisher","first-page":"201","DOI":"10.1016\/j.cplett.2006.12.080","volume":"435","year":"2007","journal-title":"Chem. Phys. Lett."},{"issue":"1\u20133","key":"2026091506582110200_c16","doi-asserted-by":"publisher","first-page":"86","DOI":"10.1016\/j.theochem.2009.05.033","volume":"909","year":"2009","journal-title":"J.\u00a0Mol. Struct.: THEOCHEM"},{"issue":"4\u20136","key":"2026091506582110200_c17","doi-asserted-by":"publisher","first-page":"500","DOI":"10.1016\/j.cplett.2006.02.092","volume":"422","year":"2006","journal-title":"Chem. Phys. Lett."},{"issue":"4\u20136","key":"2026091506582110200_c18","doi-asserted-by":"publisher","first-page":"633","DOI":"10.1016\/j.cplett.2006.08.094","volume":"429","year":"2006","journal-title":"Chem. Phys. Lett."},{"issue":"46","key":"2026091506582110200_c19","doi-asserted-by":"publisher","first-page":"14065","DOI":"10.1021\/ja034034t","volume":"125","year":"2003","journal-title":"J.\u00a0Am. Chem. Soc."},{"issue":"9","key":"2026091506582110200_c20","doi-asserted-by":"publisher","first-page":"2062","DOI":"10.1021\/ja993145i","volume":"122","year":"2000","journal-title":"J.\u00a0Am. Chem. Soc."},{"issue":"1\u20133","key":"2026091506582110200_c21","doi-asserted-by":"publisher","first-page":"37","DOI":"10.1016\/j.cplett.2008.11.009","volume":"467","year":"2008","journal-title":"Chem. Phys. Lett."},{"issue":"26","key":"2026091506582110200_c22","doi-asserted-by":"publisher","first-page":"8227","DOI":"10.1021\/jp062300u","volume":"110","year":"(2006","journal-title":"J.\u00a0Phys. Chem. A"},{"key":"2026091506582110200_c23","volume-title":"Principles of Nucleic Acid Structure","year":"2013"},{"key":"2026091506582110200_c24","doi-asserted-by":"publisher","first-page":"91","DOI":"10.1016\/j.molstruc.2015.08.003","volume":"1101","year":"2015","journal-title":"J.\u00a0Mol. Struct."},{"key":"2026091506582110200_c25","doi-asserted-by":"publisher","first-page":"74","DOI":"10.1016\/j.molstruc.2015.04.037","volume":"1096","year":"2015","journal-title":"J.\u00a0Mol. Struct."},{"key":"2026091506582110200_c26","doi-asserted-by":"publisher","first-page":"118","DOI":"10.1016\/j.molstruc.2015.03.046","volume":"1094","year":"2015","journal-title":"J.\u00a0Mol. Struct."},{"key":"2026091506582110200_c27","doi-asserted-by":"publisher","first-page":"6","DOI":"10.1016\/j.saa.2014.04.149","volume":"132","year":"2014","journal-title":"Spectrochim. Acta, Part A"},{"key":"2026091506582110200_c28","doi-asserted-by":"publisher","first-page":"41","DOI":"10.1016\/j.comptc.2014.06.027","volume":"1045","year":"2014","journal-title":"Comput. Theor. Chem."},{"issue":"8","key":"2026091506582110200_c29","doi-asserted-by":"publisher","first-page":"2388","DOI":"10.1246\/bcsj.46.2388","volume":"46","year":"1973","journal-title":"Bull. Chem. Soc. Jpn."},{"issue":"10","key":"2026091506582110200_c30","doi-asserted-by":"publisher","first-page":"o566","DOI":"10.1107\/S010827010802979X","volume":"64","year":"2008","journal-title":"Acta Crystallogr., Sect. C: Cryst. Struct. Commun."},{"issue":"1\u20133","key":"2026091506582110200_c31","doi-asserted-by":"publisher","first-page":"160","DOI":"10.1016\/j.molstruc.2007.03.020","volume":"873","year":"2008","journal-title":"J.\u00a0Mol. Struct."},{"issue":"12","key":"2026091506582110200_c32","doi-asserted-by":"publisher","first-page":"o3058","DOI":"10.1107\/S1600536809046571","volume":"65","year":"2009","journal-title":"Acta Crystallogr., Sect. E: Struct. Rep. Online"},{"issue":"8","key":"2026091506582110200_c33","doi-asserted-by":"publisher","first-page":"o414","DOI":"10.1107\/S0108270110026430","volume":"66","year":"2010","journal-title":"Acta Crystallogr., Sect. C: Cryst. Struct. Commun."},{"issue":"3","key":"2026091506582110200_c34","doi-asserted-by":"publisher","first-page":"1419","DOI":"10.1021\/cg901412d","volume":"10","year":"2010","journal-title":"Cryst. Growth Des."},{"issue":"39","key":"2026091506582110200_c35","doi-asserted-by":"publisher","first-page":"7573","DOI":"10.1039\/C6CE01534D","volume":"18","year":"2016","journal-title":"CrystEngComm"},{"issue":"3","key":"2026091506582110200_c36","doi-asserted-by":"publisher","first-page":"1700118","DOI":"10.1002\/crat.201700118","volume":"53","year":"2018","journal-title":"Cryst. Res. Technol."},{"issue":"1","key":"2026091506582110200_c37","doi-asserted-by":"publisher","first-page":"42","DOI":"10.1186\/1752-153X-8-42","volume":"8","year":"2014","journal-title":"Chem. Cent. J."},{"key":"2026091506582110200_c38","doi-asserted-by":"publisher","first-page":"703","DOI":"10.1016\/j.molstruc.2017.06.053","volume":"1146","year":"2017","journal-title":"J.\u00a0Mol. Struct."},{"issue":"2","key":"2026091506582110200_c39","doi-asserted-by":"publisher","first-page":"664","DOI":"10.1002\/jps.22805","volume":"101","year":"2012","journal-title":"J.\u00a0Pharm. Sci."},{"issue":"22","key":"2026091506582110200_c40","doi-asserted-by":"publisher","first-page":"4732","DOI":"10.1039\/C3CE42156B","volume":"16","year":"2014","journal-title":"CrystEngComm"},{"issue":"6","key":"2026091506582110200_c41","doi-asserted-by":"publisher","first-page":"3350","DOI":"10.1021\/acs.cgd.7b00322","volume":"17","year":"2017","journal-title":"Cryst. Growth Des."},{"issue":"11","key":"2026091506582110200_c42","doi-asserted-by":"publisher","first-page":"e02669","DOI":"10.1016\/j.heliyon.2019.e02669","volume":"5","year":"2019","journal-title":"Heliyon"},{"key":"2026091506582110200_c43","first-page":"1045","article-title":"Role of gallic acid in cardiovascular disorders","volume-title":"Polyphenols in Human Health and Disease","author":"Watson","year":"2014"},{"issue":"8","key":"2026091506582110200_c44","doi-asserted-by":"publisher","first-page":"2653","DOI":"10.1002\/jps.23212","volume":"101","year":"2012","journal-title":"J.\u00a0Pharm. Sci."},{"key":"2026091506582110200_c45","doi-asserted-by":"crossref","first-page":"149","DOI":"10.1016\/B978-0-08-101033-4.00005-X","article-title":"Five-membered heterocycles","volume-title":"The Chemistry of Heterocycles","year":"2019"},{"issue":"18","key":"2026091506582110200_c46","doi-asserted-by":"publisher","first-page":"3687","DOI":"10.1016\/S0040-4039(03)00685-3","volume":"44","year":"2003","journal-title":"Tetrahedron Lett."},{"issue":"1","key":"2026091506582110200_c47","doi-asserted-by":"publisher","first-page":"9","DOI":"10.1016\/S1463-0184(02)00002-3","volume":"5","year":"2002","journal-title":"Cryst. Eng."},{"issue":"3","key":"2026091506582110200_c48","doi-asserted-by":"publisher","first-page":"323","DOI":"10.1021\/mp0601345","volume":"4","year":"2007","journal-title":"Mol. Pharmaceutics"},{"issue":"4","key":"2026091506582110200_c49","doi-asserted-by":"publisher","first-page":"1122","DOI":"10.1039\/d4qo02024c","volume":"12","year":"2025","journal-title":"Org. Chem. Front."},{"key":"2026091506582110200_c50","doi-asserted-by":"publisher","first-page":"216035","DOI":"10.1016\/j.ccr.2024.216035","volume":"517","year":"2024","journal-title":"Coord. Chem. Rev."},{"issue":"16","key":"2026091506582110200_c51","doi-asserted-by":"publisher","first-page":"5789","DOI":"10.1039\/c4cs00129j","volume":"43","year":"2014","journal-title":"Chem. Soc. Rev."},{"issue":"3","key":"2026091506582110200_c52","doi-asserted-by":"publisher","first-page":"199","DOI":"10.1080\/08893110500245899","volume":"11","year":"2005","journal-title":"Crystallogr. Rev."},{"issue":"100","key":"2026091506582110200_c53","doi-asserted-by":"publisher","first-page":"608","DOI":"10.1039\/B511944H","volume":"7","year":"2005","journal-title":"CrystEngComm"},{"issue":"40","key":"2026091506582110200_c54","doi-asserted-by":"publisher","first-page":"9791","DOI":"10.1021\/jp306169f","volume":"116","year":"2012","journal-title":"J.\u00a0Phys. Chem. A"},{"issue":"17","key":"2026091506582110200_c55","doi-asserted-by":"publisher","first-page":"174108","DOI":"10.1063\/1.4979993","volume":"146","year":"2017","journal-title":"J.\u00a0Chem. Phys."},{"issue":"8","key":"2026091506582110200_c56","doi-asserted-by":"publisher","first-page":"084102","DOI":"10.1063\/1.2831537","volume":"128","year":"2008","journal-title":"J.\u00a0Chem. Phys."},{"issue":"8","key":"2026091506582110200_c57","doi-asserted-by":"publisher","first-page":"4052","DOI":"10.1021\/acs.jctc.8b00261","volume":"14","year":"2018","journal-title":"J.\u00a0Chem. Theory Comput."},{"issue":"8","key":"2026091506582110200_c58","doi-asserted-by":"publisher","first-page":"5165","DOI":"10.1021\/acs.jctc.1c00535","volume":"17","year":"2021","journal-title":"J.\u00a0Chem. Theory Comput."},{"key":"2026091506582110200_c59","doi-asserted-by":"publisher","first-page":"377","DOI":"10.3389\/fchem.2019.00377","volume":"7","year":"2019","journal-title":"Front. Chem."},{"issue":"38","key":"2026091506582110200_c60","doi-asserted-by":"publisher","first-page":"11882","DOI":"10.1039\/d5gc03797b","volume":"27","year":"2025","journal-title":"Green Chem."},{"issue":"6","key":"2026091506582110200_c61","doi-asserted-by":"publisher","first-page":"2931","DOI":"10.1021\/cg500226z","volume":"14","year":"2014","journal-title":"Cryst. Growth Des."},{"issue":"3","key":"2026091506582110200_c62","doi-asserted-by":"publisher","first-page":"347","DOI":"10.1021\/mp0700054","volume":"4","year":"2007","journal-title":"Mol. Pharmaceutics"},{"issue":"49","key":"2026091506582110200_c63","doi-asserted-by":"publisher","first-page":"12895","DOI":"10.1021\/ja981405a","volume":"120","year":"1998","journal-title":"J.\u00a0Am. Chem. Soc."},{"issue":"19","key":"2026091506582110200_c64","doi-asserted-by":"publisher","first-page":"4857","DOI":"10.1021\/ja00995a007","volume":"89","year":"1967","journal-title":"J.\u00a0Am. Chem. Soc."},{"key":"2026091506582110200_c65","doi-asserted-by":"publisher","first-page":"112200","DOI":"10.1016\/j.ejmech.2020.112200","volume":"192","year":"2020","journal-title":"Eur. J. Med. Chem."},{"key":"2026091506582110200_c66","year":"2012"},{"issue":"1","key":"2026091506582110200_c67","doi-asserted-by":"publisher","first-page":"3","DOI":"10.1107\/S2053229614024218","volume":"71","year":"2015","journal-title":"Acta Crystallogr., Sect. C: Struct. Chem."},{"issue":"5","key":"2026091506582110200_c68","doi-asserted-by":"publisher","first-page":"e1600192","DOI":"10.1126\/sciadv.1600192","volume":"2","year":"2016","journal-title":"Sci. Adv."},{"issue":"3","key":"2026091506582110200_c69","doi-asserted-by":"publisher","first-page":"279","DOI":"10.1107\/S0021889887012755","volume":"21","year":"1988","journal-title":"J.\u00a0Appl. Crystallogr."},{"issue":"9","key":"2026091506582110200_c70","doi-asserted-by":"publisher","first-page":"13643","DOI":"10.3390\/molecules190913643","volume":"19","year":"2014","journal-title":"Molecules"},{"issue":"7","key":"2026091506582110200_c71","doi-asserted-by":"publisher","first-page":"1523","DOI":"10.1071\/CH9731523","volume":"26","year":"1973","journal-title":"Aust. J. Chem."},{"key":"2026091506582110200_c72","doi-asserted-by":"publisher","first-page":"148","DOI":"10.1016\/j.jmr.2013.10.001","volume":"241","year":"2014","journal-title":"J.\u00a0Magn. Reson."},{"issue":"2","key":"2026091506582110200_c73","doi-asserted-by":"publisher","first-page":"025002","DOI":"10.1088\/2043-6262\/ac6c22","volume":"13","year":"2022","journal-title":"Adv. Nat. Sci: Nanosci. Nanotechnol."},{"issue":"15","key":"2026091506582110200_c74","doi-asserted-by":"publisher","first-page":"2322","DOI":"10.1039\/c8qo00519b","volume":"5","year":"2018","journal-title":"Org. Chem. Front."},{"issue":"13","key":"2026091506582110200_c75","doi-asserted-by":"publisher","first-page":"2385","DOI":"10.1016\/0584-8539(95)01479-9","volume":"51","year":"1995","journal-title":"Spectrochim. Acta, Part A"},{"issue":"3","key":"2026091506582110200_c76","doi-asserted-by":"publisher","first-page":"437","DOI":"10.1002\/ajoc.201900708","volume":"9","year":"2020","journal-title":"Asian J. Org. Chem."},{"issue":"11","key":"2026091506582110200_c77","doi-asserted-by":"publisher","first-page":"546","DOI":"10.1021\/ed039p546","volume":"39","year":"1962","journal-title":"J.\u00a0Chem. Educ."},{"issue":"1","key":"2026091506582110200_c78","doi-asserted-by":"publisher","first-page":"36","DOI":"10.1139\/v64-006","volume":"42","year":"1964","journal-title":"Can. J. Chem."},{"issue":"5890","key":"2026091506582110200_c79","doi-asserted-by":"publisher","first-page":"792","DOI":"10.1126\/science.1158722","volume":"321","year":"2008","journal-title":"Science"},{"issue":"1","key":"2026091506582110200_c80","doi-asserted-by":"publisher","first-page":"289","DOI":"10.1021\/cr200107z","volume":"112","year":"2012","journal-title":"Chem. Rev."},{"issue":"8","key":"2026091506582110200_c81","doi-asserted-by":"publisher","first-page":"1554","DOI":"10.1021\/jp061633o","volume":"111","year":"2007","journal-title":"J.\u00a0Phys. Chem. A"},{"issue":"14","key":"2026091506582110200_c82","doi-asserted-by":"publisher","first-page":"146401","DOI":"10.1103\/PhysRevLett.100.146401","volume":"100","year":"2008","journal-title":"Phys. Rev. Lett."},{"issue":"2","key":"2026091506582110200_c83","doi-asserted-by":"publisher","first-page":"e1631","DOI":"10.1002\/wcms.1631","volume":"13","year":"2023","journal-title":"WIREs Comput. Mol. Sci."},{"key":"2026091506582110200_c84","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1063\/1.1390175","volume":"577","year":"2001","journal-title":"AIP Conf. Proc."},{"issue":"9","key":"2026091506582110200_c85","doi-asserted-by":"publisher","first-page":"743","DOI":"10.1557\/mrs.2013.178","volume":"38","year":"2013","journal-title":"MRS Bull."},{"key":"2026091506582110200_c86","doi-asserted-by":"publisher","first-page":"12","DOI":"10.1016\/j.chemphys.2017.05.020","volume":"493","year":"2017","journal-title":"Chem. Phys."},{"issue":"1","key":"2026091506582110200_c87","doi-asserted-by":"publisher","first-page":"257","DOI":"10.1021\/acs.jpca.8b10240","volume":"123","year":"2019","journal-title":"J.\u00a0Phys. Chem. A"},{"issue":"18","key":"2026091506582110200_c88","doi-asserted-by":"publisher","first-page":"e70175","DOI":"10.1002\/jcc.70175","volume":"46","year":"2025","journal-title":"J.\u00a0Comput. Chem."},{"key":"2026091506582110200_c89","volume-title":"Gaussian 16, Revision A.02","year":"2016"},{"issue":"18","key":"2026091506582110200_c90","doi-asserted-by":"publisher","first-page":"3297","DOI":"10.1039\/B508541A","volume":"7","year":"2005","journal-title":"Phys. Chem. Chem. Phys."},{"key":"2026091506582110200_c91","doi-asserted-by":"publisher","first-page":"157677","DOI":"10.1016\/j.cej.2024.157677","volume":"501","year":"2024","journal-title":"Chem. Eng. J."},{"issue":"1","key":"2026091506582110200_c92","doi-asserted-by":"publisher","first-page":"263","DOI":"10.1021\/ct300715s","volume":"9","year":"2013","journal-title":"J.\u00a0Chem. Theory Comput."},{"issue":"11","key":"2026091506582110200_c93","doi-asserted-by":"publisher","first-page":"5725","DOI":"10.1021\/acs.jctc.8b00842","volume":"14","year":"2018","journal-title":"J.\u00a0Chem. Theory Comput."},{"issue":"30","key":"2026091506582110200_c94","doi-asserted-by":"publisher","first-page":"2562","DOI":"10.1002\/jcc.26411","volume":"41","year":"2020","journal-title":"J.\u00a0Comput. Chem."},{"issue":"21","key":"2026091506582110200_c95","doi-asserted-by":"publisher","first-page":"9904","DOI":"10.1039\/C3CP54374A","volume":"16","year":"2014","journal-title":"Phys. Chem. Chem. Phys."},{"issue":"21","key":"2026091506582110200_c96","doi-asserted-by":"publisher","first-page":"214110","DOI":"10.1063\/1.4952647","volume":"144","year":"2016","journal-title":"J.\u00a0Chem. Phys."},{"issue":"50","key":"2026091506582110200_c97","doi-asserted-by":"publisher","first-page":"12868","DOI":"10.1021\/jp801805p","volume":"112","year":"2008","journal-title":"J.\u00a0Phys. Chem. A"},{"issue":"1","key":"2026091506582110200_c98","doi-asserted-by":"publisher","first-page":"3","DOI":"10.1021\/jp710179r","volume":"112","year":"2008","journal-title":"J.\u00a0Phys. Chem. A"},{"issue":"27","key":"2026091506582110200_c99","doi-asserted-by":"publisher","first-page":"2327","DOI":"10.1002\/jcc.23391","volume":"34","year":"2013","journal-title":"J.\u00a0Comput. Chem."},{"key":"2026091506582110200_c100","doi-asserted-by":"publisher","first-page":"121","DOI":"10.1016\/j.cplett.2012.04.045","volume":"538","year":"2012","journal-title":"Chem. Phys. Lett."},{"issue":"2","key":"2026091506582110200_c101","doi-asserted-by":"publisher","first-page":"291","DOI":"10.1021\/ct100466k","volume":"7","year":"2011","journal-title":"J.\u00a0Chem. Theory Comput."},{"issue":"22","key":"2026091506582110200_c102","doi-asserted-by":"publisher","first-page":"224103","DOI":"10.1063\/5.0174988","volume":"159","year":"2023","journal-title":"J.\u00a0Chem. Phys."},{"issue":"9","key":"2026091506582110200_c103","doi-asserted-by":"publisher","first-page":"4735","DOI":"10.1021\/acs.jctc.9b00013","volume":"15","year":"2019","journal-title":"J.\u00a0Chem. Theory Comput."},{"issue":"17","key":"2026091506582110200_c104","doi-asserted-by":"publisher","first-page":"174105","DOI":"10.1063\/1.3244209","volume":"131","year":"2009","journal-title":"J.\u00a0Chem. Phys."},{"issue":"20","key":"2026091506582110200_c105","doi-asserted-by":"publisher","first-page":"201102","DOI":"10.1063\/1.5097164","volume":"150","year":"2019","journal-title":"J.\u00a0Chem. Phys."},{"issue":"13","key":"2026091506582110200_c106","doi-asserted-by":"publisher","first-page":"134101","DOI":"10.1063\/1.4821834","volume":"139","year":"2013","journal-title":"J.\u00a0Chem. Phys."},{"issue":"22","key":"2026091506582110200_c107","doi-asserted-by":"publisher","first-page":"224108","DOI":"10.1063\/5.0004608","volume":"152","year":"2020","journal-title":"J.\u00a0Chem. Phys."},{"issue":"11","key":"2026091506582110200_c108","doi-asserted-by":"publisher","first-page":"114112","DOI":"10.1063\/5.0246763","volume":"162","year":"2025","journal-title":"J.\u00a0Chem. Phys."},{"issue":"3A","key":"2026091506582110200_c109","doi-asserted-by":"publisher","first-page":"A796","DOI":"10.1103\/PhysRev.139.A796","volume":"139","year":"1965","journal-title":"Phys. Rev."},{"issue":"3","key":"2026091506582110200_c110","doi-asserted-by":"publisher","first-page":"237","DOI":"10.1088\/0034-4885\/61\/3\/002","volume":"61","year":"1998","journal-title":"Rep. Prog. Phys."},{"issue":"5","key":"2026091506582110200_c111","doi-asserted-by":"publisher","first-page":"053020","DOI":"10.1088\/1367-2630\/14\/5\/053020","volume":"14","year":"2012","journal-title":"New J. Phys."},{"issue":"8","key":"2026091506582110200_c112","doi-asserted-by":"publisher","first-page":"3623","DOI":"10.1021\/acs.jctc.6b00380","volume":"12","year":"2016","journal-title":"J.\u00a0Chem. Theory Comput."},{"issue":"2","key":"2026091506582110200_c113","doi-asserted-by":"publisher","first-page":"024109","DOI":"10.1063\/5.0006074","volume":"153","year":"2020","journal-title":"J.\u00a0Chem. Phys."},{"issue":"5","key":"2026091506582110200_c114","doi-asserted-by":"publisher","first-page":"893","DOI":"10.1021\/cr00005a013","volume":"91","year":"1991","journal-title":"Chem. Rev."},{"issue":"1","key":"2026091506582110200_c115","doi-asserted-by":"publisher","first-page":"9","DOI":"10.1021\/ar00109a003","volume":"18","year":"1985","journal-title":"Acc. Chem. Res."},{"key":"2026091506582110200_c116","year":"2012"},{"issue":"16","key":"2026091506582110200_c117","doi-asserted-by":"publisher","first-page":"3040","DOI":"10.1139\/v77-422","volume":"55","year":"1977","journal-title":"Can. J. Chem."},{"issue":"6","key":"2026091506582110200_c118","doi-asserted-by":"publisher","first-page":"1389","DOI":"10.1021\/ja00500a006","volume":"101","year":"1979","journal-title":"J.\u00a0Am. Chem. Soc."},{"issue":"6","key":"2026091506582110200_c119","doi-asserted-by":"publisher","first-page":"2871","DOI":"10.1063\/1.440457","volume":"73","year":"1980","journal-title":"J.\u00a0Chem. Phys."},{"issue":"9","key":"2026091506582110200_c120","doi-asserted-by":"publisher","first-page":"4316","DOI":"10.1063\/1.438006","volume":"70","year":"1979","journal-title":"J.\u00a0Chem. Phys."},{"issue":"8","key":"2026091506582110200_c121","doi-asserted-by":"publisher","first-page":"893","DOI":"10.1088\/0034-4885\/44\/8\/002","volume":"44","year":"1981","journal-title":"Rep. Prog. Phys."},{"issue":"5","key":"2026091506582110200_c122","doi-asserted-by":"publisher","first-page":"1943","DOI":"10.1063\/1.446956","volume":"80","year":"1984","journal-title":"J.\u00a0Chem. Phys."},{"issue":"18","key":"2026091506582110200_c123","doi-asserted-by":"publisher","first-page":"6498","DOI":"10.1021\/ja100936w","volume":"132","year":"2010","journal-title":"J.\u00a0Am. Chem. Soc."},{"issue":"5","key":"2026091506582110200_c124","doi-asserted-by":"publisher","first-page":"580","DOI":"10.1002\/jcc.22885","volume":"33","year":"2012","journal-title":"J.\u00a0Comput. Chem."},{"issue":"1","key":"2026091506582110200_c125","doi-asserted-by":"publisher","first-page":"33","DOI":"10.1016\/0263-7855(96)00018-5","volume":"14","year":"1996","journal-title":"J.\u00a0Mol. Graphics"},{"key":"2026091506582110200_c126","article-title":"Chemcraft 1.6-graphical software for visualization of quantum chemistry computations"},{"key":"2026091506582110200_c127","doi-asserted-by":"publisher","first-page":"1429","DOI":"10.1002\/jcc.23266","volume":"34","year":"2013","journal-title":"J. Comput. Chem."},{"issue":"45","key":"2026091506582110200_c128","doi-asserted-by":"publisher","first-page":"20104","DOI":"10.1039\/C1CP22592H","volume":"13","year":"2011","journal-title":"Phys. Chem. Chem. Phys."},{"issue":"4","key":"2026091506582110200_c129","doi-asserted-by":"publisher","first-page":"1918","DOI":"10.1021\/ct301064t","volume":"9","year":"2013","journal-title":"J.\u00a0Chem. Theory Comput."},{"issue":"2","key":"2026091506582110200_c130","doi-asserted-by":"publisher","first-page":"832","DOI":"10.1021\/ct500986b","volume":"11","year":"2015","journal-title":"J.\u00a0Chem. Theory Comput."},{"issue":"9","key":"2026091506582110200_c131","doi-asserted-by":"publisher","first-page":"1701","DOI":"10.1021\/jp508422u","volume":"119","year":"2015","journal-title":"J.\u00a0Phys. Chem. A"},{"issue":"31","key":"2026091506582110200_c132","doi-asserted-by":"publisher","first-page":"20905","DOI":"10.1039\/C6CP00688D","volume":"18","year":"2016","journal-title":"Phys. Chem. Chem. Phys."},{"issue":"48","key":"2026091506582110200_c133","doi-asserted-by":"publisher","first-page":"32184","DOI":"10.1039\/C7CP04913G","volume":"19","year":"2017","journal-title":"Phys. Chem. Chem. Phys."},{"issue":"24","key":"2026091506582110200_c134","doi-asserted-by":"publisher","first-page":"5129","DOI":"10.1021\/acs.jpca.9b03157","volume":"123","year":"2019","journal-title":"J.\u00a0Phys. Chem. A"},{"issue":"8\u20139","key":"2026091506582110200_c135","doi-asserted-by":"publisher","first-page":"787","DOI":"10.1002\/ijch.201900114","volume":"60","year":"2020","journal-title":"Isr. J. Chem."},{"issue":"22","key":"2026091506582110200_c136","doi-asserted-by":"publisher","first-page":"1590","DOI":"10.1002\/jcc.26698","volume":"42","year":"2021","journal-title":"J.\u00a0Comput. Chem."},{"issue":"8","key":"2026091506582110200_c137","doi-asserted-by":"publisher","first-page":"3634","DOI":"10.1021\/acs.macromol.1c00351","volume":"54","year":"2021","journal-title":"Macromolecules"},{"issue":"12","key":"2026091506582110200_c138","doi-asserted-by":"publisher","first-page":"5354","DOI":"10.1021\/acs.macromol.1c00860","volume":"54","year":"2021","journal-title":"Macromolecules"},{"issue":"42","key":"2026091506582110200_c139","doi-asserted-by":"publisher","first-page":"25842","DOI":"10.1039\/D2CP03796C","volume":"24","year":"2022","journal-title":"Phys. Chem. Chem. Phys."},{"issue":"1","key":"2026091506582110200_c140","doi-asserted-by":"publisher","first-page":"e1737","DOI":"10.1002\/wcms.1737","volume":"15","year":"2025","journal-title":"WIREs Comput. Mol. Sci."},{"issue":"21","key":"2026091506582110200_c141","doi-asserted-by":"publisher","first-page":"5505","DOI":"10.1021\/jp2031384","volume":"115","year":"2011","journal-title":"J.\u00a0Phys. Chem. A"},{"issue":"6320","key":"2026091506582110200_c142","doi-asserted-by":"publisher","first-page":"49","DOI":"10.1126\/science.aah5975","volume":"355","year":"2017","journal-title":"Science"},{"issue":"6337","key":"2026091506582110200_c143","doi-asserted-by":"publisher","first-page":"496","DOI":"10.1126\/science.aam9550","volume":"356","year":"2017","journal-title":"Science"},{"issue":"12","key":"2026091506582110200_c144","doi-asserted-by":"publisher","first-page":"6068","DOI":"10.1021\/acs.jctc.7b00865","volume":"13","year":"2017","journal-title":"J.\u00a0Chem. Theory Comput."},{"issue":"22","key":"2026091506582110200_c145","doi-asserted-by":"publisher","first-page":"6385","DOI":"10.1021\/acs.jpclett.8b02855","volume":"9","year":"2018","journal-title":"J.\u00a0Phys. Chem. Lett."},{"issue":"20","key":"2026091506582110200_c146","doi-asserted-by":"publisher","first-page":"204103","DOI":"10.1063\/1.5001939","volume":"147","year":"2017","journal-title":"J.\u00a0Chem. Phys."},{"issue":"23","key":"2026091506582110200_c147","doi-asserted-by":"publisher","first-page":"14719","DOI":"10.3390\/ijms232314719","volume":"23","year":"2022","journal-title":"Int. J. Mol. Sci."},{"key":"2026091506582110200_c148","doi-asserted-by":"publisher","first-page":"115452","DOI":"10.1016\/j.poly.2021.115452","volume":"209","year":"2021","journal-title":"Polyhedron"},{"issue":"1","key":"2026091506582110200_c149","doi-asserted-by":"publisher","first-page":"293","DOI":"10.1021\/acs.jctc.1c00981","volume":"18","year":"2021","journal-title":"J.\u00a0Chem. Theory Comput."},{"issue":"38","key":"2026091506582110200_c150","doi-asserted-by":"publisher","first-page":"7997","DOI":"10.1021\/acs.jpca.3c04504","volume":"127","year":"2023","journal-title":"J.\u00a0Phys. Chem. A"},{"issue":"29","key":"2026091506582110200_c151","doi-asserted-by":"publisher","first-page":"2485","DOI":"10.1002\/jcc.26404","volume":"41","year":"2020","journal-title":"J.\u00a0Comput. Chem."},{"issue":"8","key":"2026091506582110200_c152","doi-asserted-by":"publisher","first-page":"130","DOI":"10.1007\/s00214-020-02643-7","volume":"139","year":"2020","journal-title":"Theor. Chem. Acc."},{"issue":"21","key":"2026091506582110200_c153","doi-asserted-by":"publisher","first-page":"5240","DOI":"10.1021\/jp3029769","volume":"116","year":"2012","journal-title":"J.\u00a0Phys. Chem. A"},{"issue":"12","key":"2026091506582110200_c154","doi-asserted-by":"publisher","first-page":"5005","DOI":"10.1007\/s00894-012-1496-y","volume":"18","year":"2012","journal-title":"J.\u00a0Mol. Model."},{"issue":"17","key":"2026091506582110200_c155","doi-asserted-by":"publisher","first-page":"174302","DOI":"10.1063\/5.0067570","volume":"155","year":"2021","journal-title":"J.\u00a0Chem. Phys."},{"key":"2026091506582110200_c156","doi-asserted-by":"publisher","first-page":"114188","DOI":"10.1016\/j.comptc.2023.114188","volume":"1226","year":"2023","journal-title":"Comput. Theor. Chem."},{"issue":"7","key":"2026091506582110200_c157","doi-asserted-by":"publisher","first-page":"3113","DOI":"10.1007\/s00894-011-1325-8","volume":"18","year":"2012","journal-title":"J.\u00a0Mol. Model."},{"issue":"45","key":"2026091506582110200_c158","doi-asserted-by":"publisher","first-page":"9071","DOI":"10.1021\/acs.jpca.6b07578","volume":"120","year":"2016","journal-title":"J.\u00a0Phys. Chem. A"},{"key":"2026091506582110200_c159","doi-asserted-by":"publisher","first-page":"129362","DOI":"10.1016\/j.molliq.2026.129362","volume":"447","year":"2026","journal-title":"J.\u00a0Mol. Liq."},{"issue":"5","key":"2026091506582110200_c160","doi-asserted-by":"publisher","first-page":"2240","DOI":"10.1021\/jp911047s","volume":"114","year":"2010","journal-title":"J.\u00a0Phys. Chem. A"},{"issue":"15","key":"2026091506582110200_c161","doi-asserted-by":"publisher","first-page":"9153","DOI":"10.1021\/ic4015114","volume":"52","year":"2013","journal-title":"Inorg. Chem."},{"key":"2026091506582110200_c162","doi-asserted-by":"publisher","first-page":"26","DOI":"10.1016\/j.comptc.2017.11.009","volume":"1123","year":"2018","journal-title":"Comput. Theor. Chem."},{"issue":"6","key":"2026091506582110200_c163","doi-asserted-by":"publisher","first-page":"576","DOI":"10.1002\/wcms.1193","volume":"4","year":"2014","journal-title":"Wiley Interdiscip. Rev.: Comput. Mol. Sci."},{"issue":"17","key":"2026091506582110200_c164","doi-asserted-by":"publisher","first-page":"174101","DOI":"10.1063\/1.3491272","volume":"133","year":"2010","journal-title":"J.\u00a0Chem. Phys."},{"issue":"4","key":"2026091506582110200_c165","doi-asserted-by":"publisher","first-page":"375","DOI":"10.1002\/wcms.1178","volume":"4","year":"2014","journal-title":"Wiley Interdiscip. Rev.: Comput. Mol. Sci."},{"issue":"1","key":"2026091506582110200_c166","doi-asserted-by":"publisher","first-page":"324","DOI":"10.1021\/ct300835h","volume":"9","year":"2013","journal-title":"J.\u00a0Chem. Theory Comput."},{"issue":"11","key":"2026091506582110200_c167","doi-asserted-by":"publisher","first-page":"115103","DOI":"10.1103\/PhysRevB.83.115103","volume":"83","year":"2011","journal-title":"Phys. Rev. B"},{"issue":"10","key":"2026091506582110200_c168","doi-asserted-by":"publisher","first-page":"5076","DOI":"10.1021\/acs.jctc.6b00774","volume":"12","year":"2016","journal-title":"J.\u00a0Chem. Theory Comput."},{"issue":"24","key":"2026091506582110200_c169","doi-asserted-by":"publisher","first-page":"9747","DOI":"10.1021\/j100024a016","volume":"99","year":"1995","journal-title":"J.\u00a0Phys. Chem."},{"issue":"8","key":"2026091506582110200_c170","doi-asserted-by":"publisher","first-page":"627","DOI":"10.1002\/anie.198406271","volume":"23","year":"1984","journal-title":"Angew. Chem., Int. Ed. Engl."},{"issue":"12","key":"2026091506582110200_c171","doi-asserted-by":"publisher","first-page":"5529","DOI":"10.1063\/1.1501133","volume":"117","year":"2002","journal-title":"J.\u00a0Chem. Phys."},{"issue":"1","key":"2026091506582110200_c172","doi-asserted-by":"publisher","first-page":"552","DOI":"10.1021\/jp907550k","volume":"114","year":"2010","journal-title":"J.\u00a0Phys. Chem. A"},{"issue":"42","key":"2026091506582110200_c173","doi-asserted-by":"publisher","first-page":"22935","DOI":"10.1039\/C4CP02585G","volume":"16","year":"2014","journal-title":"Phys. Chem. Chem. Phys."},{"issue":"37","key":"2026091506582110200_c174","doi-asserted-by":"publisher","first-page":"7314","DOI":"10.1021\/jp981794v","volume":"102","year":"1998","journal-title":"J.\u00a0Phys. Chem. A"},{"issue":"12","key":"2026091506582110200_c175","doi-asserted-by":"publisher","first-page":"5436","DOI":"10.1021\/ct500899h","volume":"10","year":"2014","journal-title":"J.\u00a0Chem. Theory Comput."},{"key":"2026091506582110200_c176","doi-asserted-by":"publisher","first-page":"63","DOI":"10.1016\/j.cplett.2013.03.044","volume":"568\u2013569","year":"2013","journal-title":"Chem. Phys. Lett."},{"issue":"8","key":"2026091506582110200_c177","doi-asserted-by":"publisher","first-page":"3263","DOI":"10.1021\/ct400420r","volume":"9","year":"2013","journal-title":"J.\u00a0Chem. Theory Comput."},{"issue":"1\u20133","key":"2026091506582110200_c178","doi-asserted-by":"publisher","first-page":"126","DOI":"10.1016\/j.molstruc.2009.11.021","volume":"964","year":"2010","journal-title":"J.\u00a0Mol. Struct."}],"container-title":["The Journal of Chemical Physics"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.aip.org\/aip\/jcp\/article-pdf\/doi\/10.1063\/5.0335574\/21139716\/114301_1_5.0335574.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.aip.org\/aip\/jcp\/article-pdf\/doi\/10.1063\/5.0335574\/21139716\/114301_1_5.0335574.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,15]],"date-time":"2026-09-15T10:58:32Z","timestamp":1789469912000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.aip.org\/jcp\/article\/165\/11\/114301\/3404514\/Proton-transfer-dictated-supramolecular-hydrogen"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,9,15]]},"references-count":178,"journal-issue":{"issue":"11","published-print":{"date-parts":[[2026,9,21]]}},"URL":"https:\/\/doi.org\/10.1063\/5.0335574","relation":{},"ISSN":["0021-9606","1089-7690"],"issn-type":[{"value":"0021-9606","type":"print"},{"value":"1089-7690","type":"electronic"}],"subject":[],"published-other":{"date-parts":[[2026,9,21]]},"published":{"date-parts":[[2026,9,15]]},"article-number":"114301"}}