{"id":9764,"date":"2014-05-19T12:19:06","date_gmt":"2014-05-19T10:19:06","guid":{"rendered":"https:\/\/web.computaex.es\/?page_id=9764"},"modified":"2025-08-27T12:21:07","modified_gmt":"2025-08-27T10:21:07","slug":"hydrazones-from-hydroxy-naphthaldehydes-part-2-condensations-with-aromatic-n-aminoheterocycles-and-elucidation-of-tautomeric-structures","status":"publish","type":"page","link":"https:\/\/computaex.es\/en\/publicaciones\/hydrazones-from-hydroxy-naphthaldehydes-part-2-condensations-with-aromatic-n-aminoheterocycles-and-elucidation-of-tautomeric-structures\/","title":{"rendered":"Hydrazones from hydroxy naphthaldehydes. Part 2. Condensations with aromatic N-aminoheterocycles and elucidation of tautomeric structures"},"content":{"rendered":"
\n
\n
\n

R. Fernando Mart\u00ednez,Mart\u00edn \u00c1valos,Reyes Babiano,Pedro Cintas,Mark E. Light,Jos\u00e9 L. Jim\u00e9nez,Juan C. Palacios.\u00a0Hydrazones from hydroxy naphthaldehydes. Part 2. Condensations with aromatic N-aminoheterocycles and elucidation of tautomeric structures. Tetrahedron<\/strong>. Volume 70, Issue 14, 8 April 2014, Pages 2319\u20132329.\u00a0http:\/\/dx.doi.org\/10.1016\/j.tet.2014.02.049.<\/a><\/p>\n

Abstract<\/strong>
\nThis paper extends previous studies on hydrazones<\/a>\u00a0derived from\u00a0hydroxyl<\/a>\u00a0naphthaldehydes<\/a>\u00a0to aromatic\u00a0N<\/em>-aminoheterocycles (exemplified herein by\u00a0triazole<\/a>\u00a0derivatives), in an attempt to freeze\u00a0enamine<\/a>\u00a0structures either by altering the electronic properties of the non-iminic nitrogen or through\u00a0steric hindrance<\/a>\u00a0leading to coplanar dispositions between the lone pairs. By comparing experimentally obtained results (NMR in solution and crystal data) to computationally simulated ones (via DFT calculations in the gas phase and CHCl3<\/sub>), the structures of the preferential\u00a0conformers<\/a>\u00a0and\u00a0tautomers<\/a>\u00a0can be confidently assigned. All data are consistent with enhanced stability of\u00a0imine<\/a>\u00a0forms with respect to their\u00a0enamine<\/a>\u00a0counterparts. DFT calculations have the ability to identify the orbital interactions responsible for\u00a0electron delocalization<\/a>\u00a0and the energy of intramolecular\u00a0hydrogen bonding<\/a>. In addition, all transition structures for conformational and tautomeric equilibria are located and characterized.<\/p>\n<\/div>\n<\/div>\n<\/div>\n

\n
Fuente de la publicaci\u00f3n:<\/div>\n
\n
\n