{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,21]],"date-time":"2026-08-21T13:02:42Z","timestamp":1787317362051,"version":"build-2736575974"},"reference-count":64,"publisher":"MDPI AG","issue":"11","license":[{"start":{"date-parts":[[2025,5,27]],"date-time":"2025-05-27T00:00:00Z","timestamp":1748304000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"ANID","award":["1210689"],"award-info":[{"award-number":["1210689"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>This article discloses the synthesis of four new positional isomeric zwitterionic ligands exhibiting semi-flexible and flexible characteristics\u2014n-pyridinium-1,2,3-triazole-4-carboxy-5-Acetate (n-PTCA), and n-methylpyridinium-1,2,3-triazole-4-carboxy-5-Acetate (n-MPTCA; where n = 3, 4)\u2014which were derived from an aqueous solution of the corresponding sodium salts in an acidic medium (HCl). These compounds are successfully synthesized and characterized with FT-IR and multinuclear NMR spectroscopy; likewise, proper single crystals are obtained for each compound. All compounds adopt zwitterionic forms in the solid state, which are stabilized via intermolecular proton transfer processes involving HCl and solvent molecules. A single-crystal X-ray analysis revealed how positional isomerism and molecular flexibility influence the supramolecular topology. Specifically, 3-PTCA and 4-PTCA exhibit isomorphic hydrogen bond networks, while 3-MPTCA and 4-MPTCA display distinct packing motifs, attributed to the presence of a methylene spacer between the pyridinium and triazole rings. The Hirshfeld surface analysis quantitatively confirmed the dominance of O\u00b7\u00b7\u00b7H\/H\u00b7\u00b7\u00b7O and N\u00b7\u00b7\u00b7H\/H\u00b7\u00b7\u00b7N interactions in the solid-state architecture. These strong hydrogen-bonding networks are indicative of the potential proton-conductive behavior in the crystalline state, positioning these compounds as promising candidates for applications in proton-conducting materials. The structural insights gained underscore the pivotal role of molecular topology in tailoring crystal packing, with implications for the rational design of zwitterionic ligands in functional materials, including MOFs and coordination polymers. The calculated HOMO-LUMO energy gaps reveal a significant electronic variability among the ligands, influenced primarily by the positional isomerism and structural flexibility introduced by the methylene spacer.<\/jats:p>","DOI":"10.3390\/ijms26115123","type":"journal-article","created":{"date-parts":[[2025,5,28]],"date-time":"2025-05-28T03:52:08Z","timestamp":1748404328000},"page":"5123","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Structure\u2013Property Relationships in Zwitterionic Pyridinium\u2013Triazole Ligands: Insights from Crystal Engineering and Hirshfeld Surface Analysis"],"prefix":"10.3390","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-3970-2387","authenticated-orcid":false,"given":"Gerzon E.","family":"Delgado","sequence":"first","affiliation":[{"name":"Departamento de Qu\u00edmica, Facultad de Ciencias, Universidad de los Andes, M\u00e9rida 5101, Venezuela"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5952-7083","authenticated-orcid":false,"given":"Jonathan","family":"Cisterna","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica, Facultad de Ciencias, Universidad de Cat\u00f3lica del Norte, Sede Casa Central, Av. Angamos 0610, Antofagasta 1270709, Chile"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0804-3166","authenticated-orcid":false,"given":"Jaime","family":"Llanos","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica, Facultad de Ciencias, Universidad de Cat\u00f3lica del Norte, Sede Casa Central, Av. Angamos 0610, Antofagasta 1270709, Chile"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7244-0265","authenticated-orcid":false,"given":"Ruth","family":"Pulido","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica, Universidad de Antofagasta, Av. Universidad de Antofagasta 02800, Campus Coloso, Antofagasta 1240000, Chile"},{"name":"Instituto Universitario de Ciencia de Materiales \u201cNicol\u00e1s Cabrera\u201d (INC), Universidad Aut\u00f3noma de Madrid, Campus de Cantoblanco, 28049 Madrid, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0949-277X","authenticated-orcid":false,"given":"Nelson","family":"Naveas","sequence":"additional","affiliation":[{"name":"Instituto Universitario de Ciencia de Materiales \u201cNicol\u00e1s Cabrera\u201d (INC), Universidad Aut\u00f3noma de Madrid, Campus de Cantoblanco, 28049 Madrid, Spain"},{"name":"Departamento de F\u00edsica Aplicada, Universidad Aut\u00f3noma de Madrid, 28049 Madrid, Spain"},{"name":"Departamento de Ingenier\u00eda Qu\u00edmica y Procesos de Minerales, Universidad de Antofagasta, Avenida Angamos 601, Antofagasta 1270300, Chile"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pilar","family":"Narea","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica, Universidad de Antofagasta, Av. Universidad de Antofagasta 02800, Campus Coloso, Antofagasta 1240000, Chile"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1952-1020","authenticated-orcid":false,"given":"Pilar","family":"Amo-Ochoa","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Inorg\u00e1nica, Universidad Aut\u00f3noma de Madrid, 28049 Madrid, Spain"},{"name":"Institute for Advanced Research Chemistry (IAdChem), Universidad Aut\u00f3noma de Madrid, 28049 Madrid, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7529-5120","authenticated-orcid":false,"given":"F\u00e9lix","family":"Zamora","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Inorg\u00e1nica, Universidad Aut\u00f3noma de Madrid, 28049 Madrid, Spain"},{"name":"Institute for Advanced Research Chemistry (IAdChem), Universidad Aut\u00f3noma de Madrid, 28049 Madrid, Spain"},{"name":"Condensed Matter Physics Center (IFIMAC), Universidad Aut\u00f3noma de Madrid, 28049 Madrid, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0292-383X","authenticated-orcid":false,"given":"Yasna","family":"Le\u00f3n","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica, Universidad de Antofagasta, Av. 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