Patterns of hydrogen bonding in mono- and di-substituted N-arylpyrazinecarboxamides

Acta Crystallographica. Section B, Structural Science
Solange M S V WardellChristopher Glidewell

Abstract

The molecular and supramolecular structures of 18 N-arylpyrazinecarboxamides, Ar NHCO(C(4)H(3)N(2)), have been determined, including the stoichiometric monohydrate of N-(3-methoxyphenyl)pyrazinecarboxamide, and two polymorphs of N-(4-fluorophenyl)pyrazinecarboxamide having Z' values of 1 and 4, respectively. The aryl groups were selected to include the geometric isomers for a compact range of substituents, namely methyl, trifluoromethyl, fluoro, chloro, methoxy and nitro groups, which exhibit markedly varied electronic properties and markedly varied behaviour as hydrogen-bond donors and acceptors. However, not all isomers in each group could be structurally investigated. A small number of derivatives containing disubstituted aryl groups have also been included in this study. The crystal structures of the solvent-free carboxamides reported here exhibit a wide range of direction-specific intermolecular forces, including N-H...N, N-H...O, C-H...N and C-H...O hydrogen bonds, and pi...pi stacking interactions, while the structure of N-(3-methoxyphenyl)pyrazinecarboxamide monohydrate also contains O-H...N and O-H...O hydrogen bonds. The resulting supramolecular structures can be zero-, one- or two-dimensional, although no three-dimen...Continue Reading

Citations

Jan 1, 2009·Acta Crystallographica. Section E, Structure Reports Online·R Alan HowieEdward R T Tiekink
Jan 1, 2010·Acta Crystallographica. Section E, Structure Reports Online·Marcelle de Lima FerreiraEdward R T Tiekink
Jan 1, 2010·Acta Crystallographica. Section E, Structure Reports Online·Camilo H da Silva LimaEdward R T Tiekink
Jan 4, 2013·Acta Crystallographica. Section E, Structure Reports Online·Mehri Noroozi TissehHamid Reza Khavasi
Dec 10, 2013·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jan ZitkoMartin Doležal
Mar 6, 2013·Acta Crystallographica. Section C, Crystal Structure Communications·Ligia R GomesMarcus V N de Souza

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