A. Rybarczyk-Pirek, Marlena Łukomska-Rogala, Kinga Wzgarda-Raj
Oct 19, 2018
Citations
0
Influential Citations
4
Citations
Journal
Crystal Growth & Design
Abstract
Novel solid-state structures of 2-hydroxypyridine-N-oxide and its co-crystal with 3,5-dinitrobenzoic acid have been determined. The crystallographic results indicate that this pyridine derivative exists in a neutral tautomeric form in a crystal state; these results are in contrast to the 2-hydroxy, 2-mercapto, and 2-nitramino counterparts of the derivative, which were in a zwitterionic form. The phenomenon of tautomerism in this study was subsequently analyzed with quantum chemistry. The results of theoretical DFT calculations were in agreement with experimental findings (apart from the 2-nitramino derivative), indicating that, in low energy difference between the tautomeric forms, a molecule adopts a more profitable structure in terms of crystal stability, even if it is less stable in the gas phase.