{"id":9517,"date":"2011-09-05T17:21:42","date_gmt":"2011-09-05T15:21:42","guid":{"rendered":"https:\/\/web.computaex.es\/?page_id=9517"},"modified":"2025-08-27T09:24:31","modified_gmt":"2025-08-27T07:24:31","slug":"tautomerism-in-schiff-bases-the-cases-of-2-hydroxy-1-naphthaldehyde-and-1-hydroxy-2-naphthaldehyde-investigated-in-solution-and-the-solid-state","status":"publish","type":"page","link":"https:\/\/computaex.es\/en\/publicaciones\/tautomerism-in-schiff-bases-the-cases-of-2-hydroxy-1-naphthaldehyde-and-1-hydroxy-2-naphthaldehyde-investigated-in-solution-and-the-solid-state\/","title":{"rendered":"Tautomerism in Schiff bases. The cases of 2-hydroxy-1-naphthaldehyde and 1-hydroxy-2-naphthaldehyde investigated in solution and the solid state"},"content":{"rendered":"<div class=\"field field-name-field-pub-descripcion field-type-text-long field-label-hidden\">\n<div class=\"field-items\">\n<div class=\"field-item even\">\n<p>R. Fernando Mart\u00ednez, Mart\u00edn \u00c1valos, Reyes Babiano, Pedro Cintas, Jos\u00e9 L. Jim\u00e9nez, Mark E. Light and Juan C. Palacios:\u00a0<strong>Tautomerism in Schiff bases. The cases of 2-hydroxy-1-naphthaldehyde and 1-hydroxy-2-naphthaldehyde investigated in solution and the solid state<\/strong>. Organic &amp; Biomolecular Chemistry. Septiembre de 2011, 9, 8268\u20138275.<\/p>\n<p><strong>Abstract<\/strong><br \/>\nSchiff bases derived from hydroxyl naphthaldehydes and\u00a0<em>o<\/em>-substituted anilines\u00a0have been prepared and their tautomerism assessed by spectroscopic, crystallographic, and computational methods. Tautomeric equilibria have also been studied and reveal in most cases a slight preference of\u00a0imine\u00a0tautomers in solution; a fact supported by DFT calculations in the gas phase as well as incorporating\u00a0solvent\u00a0effects through the SMD model. To simulate the effect exerted by the crystal lattice on tautomer stability, we have developed a computational protocol in the case of\u00a01-<em>tert<\/em>-butyl-2-(2-hydroxy-1-naphthylmethylene)aminobenzene\u00a0whose data have been obtained experimentally at 120 K. Although a rapid\u00a0imine-enamine\u00a0interconversion may be occurring in the solid state, the\u00a0imine\u00a0tautomer becomes the most stable form and the energy difference should be related to the difference in the packing of the molecules.<\/p>\n<\/div>\n<\/div>\n<\/div>\n<div class=\"field field-name-field-pub-fuente field-type-text-long field-label-above\">\n<div class=\"field-label\">Fuente de la publicaci\u00f3n:<\/div>\n<div class=\"field-items\">\n<div class=\"field-item even\">\n<ul>\n<li><a title=\"Tautomerism in Schiff bases. The cases of 2-hydroxy-1-naphthaldehyde and 1-hydroxy-2-naphthaldehyde investigated in solution and the solid state\" href=\"http:\/\/pubs.rsc.org\/en\/content\/articlelanding\/2011\/ob\/c1ob06073b\">Tautomerism in Schiff bases. The cases of 2-hydroxy-1-naphthaldehyde and 1-hydroxy-2-naphthaldehyde investigated in solution and the solid state<\/a><\/li>\n<\/ul>\n<\/div>\n<\/div>\n<\/div>","protected":false},"excerpt":{"rendered":"<p>R. Fernando Mart\u00ednez, Mart\u00edn \u00c1valos, Reyes Babiano, Pedro Cintas, Jos\u00e9 L. Jim\u00e9nez, Mark E. Light and Juan C. Palacios:\u00a0Tautomerism in Schiff bases. The cases of 2-hydroxy-1-naphthaldehyde and 1-hydroxy-2-naphthaldehyde investigated in &#8230;<\/p>","protected":false},"author":1,"featured_media":0,"parent":1583,"menu_order":0,"comment_status":"closed","ping_status":"closed","template":"","meta":{"footnotes":""},"categories":[110,91],"tags":[],"class_list":["post-9517","page","type-page","status-publish","hentry","category-anteriores","category-publicaciones"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.1.1 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Tautomerism in Schiff bases. 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The cases of 2-hydroxy-1-naphthaldehyde and 1-hydroxy-2-naphthaldehyde investigated in solution and the solid state - Fundaci\u00f3n COMPUTAEX","robots":{"index":"index","follow":"follow","max-snippet":"max-snippet:-1","max-image-preview":"max-image-preview:large","max-video-preview":"max-video-preview:-1"},"canonical":"https:\/\/computaex.es\/en\/publicaciones\/tautomerism-in-schiff-bases-the-cases-of-2-hydroxy-1-naphthaldehyde-and-1-hydroxy-2-naphthaldehyde-investigated-in-solution-and-the-solid-state\/","og_locale":"en_US","og_type":"article","og_title":"Tautomerism in Schiff bases. The cases of 2-hydroxy-1-naphthaldehyde and 1-hydroxy-2-naphthaldehyde investigated in solution and the solid state - Fundaci\u00f3n COMPUTAEX","og_description":"R. Fernando Mart\u00ednez, Mart\u00edn \u00c1valos, Reyes Babiano, Pedro Cintas, Jos\u00e9 L. Jim\u00e9nez, Mark E. Light and Juan C. Palacios:\u00a0Tautomerism in Schiff bases. 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