Two acyclic imides: 3-bromo-N-(3-bromo-benzo-yl)-N-(pyridin-2-yl)benzamide and 3-bromo-N-(3-bromo-benzo-yl)-N-(pyrimidin-2-yl)benzamide.

Féilim Desmond,Niall Hehir,John F Gallagher

doi:10.1107/s2056989020014413

Abstract

The title compounds, C19H12Br2N2O2 and C18H11Br2N3O2, were synthesized in good yields from condensation reactions of 3-bromo-benzoyl chloride with 2-amino-pyridine or 2-amino-pyrimidine using standard condensation reaction conditions and subsequent column chromatography.

Highlights

The title compounds, C19H12Br2N2O2 and C18H11Br2N3O2, were synthesized in good yields from condensation reactions of 3-bromobenzoyl chloride with 2-aminopyridine or 2-aminopyrimidine using standard condensation reaction conditions and subsequent column chromatography
E76, 1800–1804 research communications macrocyclic imides (Evans & Gale, 2004; Mocilac & Gallagher, 2013). Both syn and anti types of acyclic imide conformation have been observed in the macrocycles
Further studies are needed to demonstrate the ease with which the two distinct conformations can interconvert in acyclic imides

Summary

Structural commentary

From the condensation reaction of meta-BrC6H4COCl with 2-aminopyridine and 2-aminopyrimidine, the benzamide and imide products were obtained and separated by standard column chromatography for each reaction. Using 2-aminopyridine, Brmo and Brmod, (I) were obtained and for 2aminopyrimidine, Brmopz and Brmopzd, (II) were isolated. Brmo and Brmopz are the (1:1) benzamide products, whereas Brmod, (I) and Brmopzd, (II) are the (2:1) acyclic imides. A comparison of acyclic imides and their key torsion angles demonstrates the range of angles observed and the key differences between the syn (carbonyl OÁ Á ÁO separations of $4.5 A ) and anti conformations (OÁ Á ÁO separations of $3.7 A ) in crystal structures (Groom et al, 2016). We have previously used the cisoid and transoid terminology for the disposition of the two C O groups; this is used to describe the orientation and direction of the C O groups/aromatic rings with respect to one another (Mocilac et al, 2018)

Supramolecular features

Database survey

Synthesis and crystallization

Refinement