Structures of (pyrazinecarbonyl)hydrazones of substituted benzaldehydes: different supramolecular arrangements from C—H···X (X = O, N, π) hydrogen bonds

✍ Scribed by Howie, R. Alan; da Silva Lima, Camilo H.; Kaiser, Carlos R.; de Souza, Marcus V. N.; Wardell, James L.; Wardell, Solange M. S. V.

• Book ID: 120330585
• Publisher: Oldenbourg Wissenschaftsverlag
• Year: 2010
• Tongue: English
• Weight: 675 KB
• Volume: 225
• Category: Article
• ISSN: 2194-4946
• DOI: 10.1524/zkri.2010.1235

✦ Synopsis

Abstract

The crystal structures of six (pyrazinecarbonyl)hydrazone di-substituted benzaldehyde derivatives [N~2~C~4~H~3~CONHN = CHC~6~H~3~XY: X,Y = 2,3-Cl~2~; 2,3-(MeO)~2~; 2,4-F~2~; 2,4-Me~2~; 3-HO—4-MeO; 3-MeO—4-HO] and one tri-substituted benzaldehyde derivative, [N~2~C~4~H~3~CONHN = CHC~6~H~2~X~3~: X~3~ = 3,4,5-(MeO)~3~] are reported. In all cases extensive intermolecular C—H···X (X = O, N or π-ring) hydrogen-bonding is present in which the the oxygen atoms of OH and OMe substituents act as hydrogen-bond acceptors and C—H bonds of methyl groups act as hydrogen-bond donors. The connectivity attained is one-dimensional in chains or ribbons in the 2,3-(OMe)~2~ and 2,4-Me~2~ derivatives, three dimensional only in the case of the 3-MeO—4-HO derivative and two dimensional in layers of molecules otherwise. It is concluded, therefore, that the bulky nature of the substituents limits the connectivity attainable in this series of compounds.