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Title:Synthesis, structural and conformational analysis of a 3 × 3 isomer grid based on nine methyl-N-(pyridyl)benzamides
Authors:Pavle Mocilac, Mark Tallon, Alan J. Lough, John F. Gallagher, 2010
Abstract: A 3 × 3 isomer grid of nine methyl-N-(pyridyl)benzamides (C13H12N2O) as Mxx (x = para-/meta-/ortho-) has been synthesized and characterised to evaluate and correlate structural relationships from both ab initio calculations (gas-phase, PCM-SMD model solvated forms) and the solid-state. The effect of methyl group (Mx) and pyridine N atom (x) substitution patterns on molecular conformations from calculations and in terms of molecular organisation is evaluated. The primary hydrogen bonding is amideN–HNpyridine in eight isomers but is amideN–HOCamide in Mpm. The N–HN interactions form C(6) chains in the Mxp series, C(5) chains in Mmm, Mom and cyclic centrosymmetric R22(8) rings in the Mxo series. Of note is the short intradimer C–Hπ(arene) interaction in Moo, one of the shortest reported in a neutral organic system CCg = 3.3875(18) Å, HCg = 2.46 Å [2.33 Å] and C–HCg = 167° [166°] [with normalised C–H distances]. Conformational features and differences between the computational calculations and crystal structures are discussed.
ICHEC Project:Molecular modelling and ab initio calculations benzamides and pyridinecarboxamides.
Publication:CrystEngComm (2010), 12, pp 3080-3090
URL: http://dx.doi.org/10.1039/C002986F
Status: Published

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