Abstract

The effect of fluorine and pyridine N atom substitution patterns on molecular structure and conformation is probed in a 3  3 isomer grid (Scheme 1) of fluoro-N-(pyridyl)benzamides (Fxx) (C12H9N2OF, x = para-/meta-/ortho-) to evaluate and correlate structural relationships between the solid-state and ab initio calculations. Physicochemical comparisons are analysed with an extended series of three related 3 x 3 isomer grids. Our analysis integrates crystal structure analyses, computational chemistry and conformational analyses together with NMR data and physicochemical trends such as melting point analysis. This study concludes structural systematics survey of four fluoro/methyl substituted benzamide/pyridinecarboxamide isomer grids.