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Issue 10, 2010
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Synthesis, structural and conformational analysis of a 3 × 3 isomer grid based on nine methyl-N-(pyridyl)benzamides

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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–H⋯Npyridine in eight isomers but is amideN–H⋯O[double bond, length as m-dash]Camide in Mpm. The N–H⋯N 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–H⋯π(arene) interaction in Moo, one of the shortest reported in a neutral organic system C⋯Cg = 3.3875(18) Å, H⋯Cg = 2.46 Å [2.33 Å] and C–H⋯Cg = 167° [166°] [with normalised C–H distances]. Conformational features and differences between the computational calculations and crystal structures are discussed.

Graphical abstract: Synthesis, structural and conformational analysis of a 3 × 3 isomer grid based on nine methyl-N-(pyridyl)benzamides

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Publication details

The article was received on 15 Feb 2010, accepted on 11 May 2010 and first published on 09 Jun 2010


Article type: Paper
DOI: 10.1039/C002986F
Citation: CrystEngComm, 2010,12, 3080-3090
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    Synthesis, structural and conformational analysis of a 3 × 3 isomer grid based on nine methyl-N-(pyridyl)benzamides

    P. Mocilac, M. Tallon, A. J. Lough and J. F. Gallagher, CrystEngComm, 2010, 12, 3080
    DOI: 10.1039/C002986F

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