Studying the gem-diol generation in imidazole and pyridine aldehyde derivatives using NMR and X-ray crystallography

JUAN MANUEL LÁZARO MARTÍNEZ; DANIEL VEGA; GUSTAVO ALBERTO MONTI; ANA KARINA CHATTAH; GRACIELA YOLANDA BULDAIN

Rio de Janeiro

Encuentro; 18th ISMAR Meeting; 2013

AUREMN

Introduction: The adduct formed upon addition of water to an aldehyde or ketone is called a hydrate or geminal diol (gem-diol). In particular, the 2-formylimidazole hydrate is a stable crystalline substance because, in order to revert to the aldehyde-form, a water molecule must be left out, and this is difficult by the electron-withdrawing character of the imidazolium cation. The aim of the present work was to study the existence and stability of the aldehyde-hydrate form of some pyridine or imidazole aldehyde derivatives commonly employed as reagents in the synthesis of active- and coordination-compounds,1,2 using solution- and solid-state NMR experiments. In addition, some of the derivatives presented here were studied through single-crystal X-ray crystallography.