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In this work, the generation of the hydrated or hemiacetal forms using pyridine\u2010 and imidazole\u2010carboxaldehyde isomers in different chemical environments was studied by Nuclear Magnetic Resonance (NMR) recorded in different media and combined with theoretical calculations. The change in the position of aldehyde group in either the pyridine or the imidazole ring had a clear effect in the course of the hydration\/hemiacetal generation reaction, which was favored in protic solvents mainly in the presence of methanol. For pyridinecarboxaldehydes, the acidity\/basicity degree of the reaction medium influenced not only the generation of the\n                    <jats:italic>gem<\/jats:italic>\n                    \u2010diol or hemiacetal forms but also the oxidation to the corresponding carboxylic acid. However, imidazolecarboxaldehyde was found to be less reactive to the nucleophilic addition of water and methanol than the other compounds in all the environments evaluated. Furthermore, both the\n                    <jats:italic>gem<\/jats:italic>\n                    \u2010diol\/hemiacetal generation and the Cannizzaro reaction products were studied in alkaline medium.\n                  <\/jats:p>","DOI":"10.1002\/open.202400411","type":"journal-article","created":{"date-parts":[[2025,1,6]],"date-time":"2025-01-06T00:36:06Z","timestamp":1736123766000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Reactivity of Imidazole\u2010 and Pyridine\u2010Carboxaldehydes for\n                    <i>Gem<\/i>\n                    \u2010Diol and Hemiacetal Generation: Theoretical and Experimental Insights"],"prefix":"10.1002","volume":"14","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-9296-5939","authenticated-orcid":false,"given":"Ayel\u00e9n F.","family":"Crespi","sequence":"first","affiliation":[{"name":"Universidad de Buenos Aires Facultad de Farmacia y Bioqu\u00edmica Department of Chemistry  Ciudad Aut\u00f3noma de Buenos Aires 1113 Argentina"},{"name":"CONICET \u2013 Universidad de Buenos Aires Instituto de Qu\u00edmica y Metabolismo del F\u00e1rmaco (IQUIMEFA-UBA-CONICET)  Ciudad Aut\u00f3noma de Buenos Aires 1113 Argentina"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1166-0832","authenticated-orcid":false,"given":"Emiliano","family":"Barrionuevo","sequence":"additional","affiliation":[{"name":"CONICET \u2013 Universidad de Buenos Aires Instituto de Qu\u00edmica y Metabolismo del F\u00e1rmaco (IQUIMEFA-UBA-CONICET)  Ciudad Aut\u00f3noma de Buenos Aires 1113 Argentina"},{"name":"Universidad de Buenos Aires Facultad de Farmacia y Bioqu\u00edmica Department of Pharmacology  Ciudad Aut\u00f3noma de Buenos Aires 1113 Argentina"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9245-432X","authenticated-orcid":false,"given":"Gabriel","family":"Jasinski","sequence":"additional","affiliation":[{"name":"CONICET \u2013 Universidad de Buenos Aires Instituto de Qu\u00edmica y Metabolismo del F\u00e1rmaco (IQUIMEFA-UBA-CONICET)  Ciudad Aut\u00f3noma de Buenos Aires 1113 Argentina"},{"name":"Universidad de Buenos Aires Facultad de Farmacia y Bioqu\u00edmica Department of Pharmacology  Ciudad Aut\u00f3noma de Buenos Aires 1113 Argentina"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5625-3627","authenticated-orcid":false,"given":"Albertina G.","family":"Moglioni","sequence":"additional","affiliation":[{"name":"CONICET \u2013 Universidad de Buenos Aires Instituto de Qu\u00edmica y Metabolismo del F\u00e1rmaco (IQUIMEFA-UBA-CONICET)  Ciudad Aut\u00f3noma de Buenos Aires 1113 Argentina"},{"name":"Universidad de Buenos Aires Facultad de Farmacia y Bioqu\u00edmica Department of Pharmacology  Ciudad Aut\u00f3noma de Buenos Aires 1113 Argentina"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Daniel","family":"Vega","sequence":"additional","affiliation":[{"name":"Department of Condensed Matter Physics Comisi\u00f3n Nacional de Energ\u00eda At\u00f3mica  San Mart\u00edn, Buenos Aires 1650 Argentina"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7189-6874","authenticated-orcid":false,"given":"Juan M.","family":"L\u00e1zaro\u2010Mart\u00ednez","sequence":"additional","affiliation":[{"name":"Universidad de Buenos Aires Facultad de Farmacia y Bioqu\u00edmica Department of Chemistry  Ciudad Aut\u00f3noma de Buenos Aires 1113 Argentina"},{"name":"CONICET \u2013 Universidad de Buenos Aires Instituto de Qu\u00edmica y Metabolismo del F\u00e1rmaco (IQUIMEFA-UBA-CONICET)  Ciudad Aut\u00f3noma de Buenos Aires 1113 Argentina"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,1,5]]},"reference":[{"key":"e_1_2_7_1_1","doi-asserted-by":"publisher","DOI":"10.1039\/tf9605601281"},{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ica.2011.11.013"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol401663u"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol800021r"},{"key":"e_1_2_7_5_1","unstructured":"E.\u2005J. 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