Synthesis, spectroscopic and X-ray structure analyses of two N-[(3′-aryl) prop-2′-ynyl]-N,N′-1,2-phenylene di-p-tosylamides

Abstract

Two N-substituted phenylene diamines C27H24N2S3O4 (I) and C29H25N2S2O4Cl (II), acyclic precursors leading to quinoxaline derivatives, have been synthesized, and characterized by spectroscopic and X-ray structural studies. The molecules of compounds (I) and (II) are linked through intermolecular N—H···O and C—H···O hydrogen bonds into centrosymmetric dimers, with characteristic R 2 2(14) and R 2 2(26) rings, which combine to form infinite polymeric chains propagating along the [001] direction. Additional intermolecular C—H···O hydrogen bonds connect the molecules of (I) into two-dimensional sheet of R 4 4(32) rings in the ab-plane and one-dimensional C(7) chain propagating along the [100] direction in (II). The combination of two-dimensional sheets in the ab-plane (in I) and one-dimensional C(7) chains along the [100] direction (in II) with the polymeric chains along the [001] direction generates a three-dimensional supramolecular assembly in (I) and a two-dimensional framework in (II).