Crystal structures of 2-[5-nitrothien-2-yl)- CH=N–NR–CO(CH2)n]thiophene compounds (R = H or Me; n = 0 or 1)

Authors: Cardoso, L.N.F.; Nogueira, T.C.M.; Kaiser, C.R.; Wardell, J.L.; Wardell, S.M.S.V.; De Souza, M.V.N.


Abstract

The crystal structures of four acylhydrazonyl derivatives of thiophene, 2-(ArCH=N–NHCO)- thiophene, (1a), 2-(ArCH=N–NMeCO)-thiophene, (2a), 2-(ArCH=N–NHCOCH2)-thiophene, (3a) and 2-(ArCH= N–NMeCOCH2)-thiophene, (4a) [in each case Ar= 5-nitrothien-2-yl] are reported. The molecular conformations of 1a and 2a are near planar, while those of 3a and 4a exhibit bends at the methylene carbon. Methylations at the hydrazonyl groups in 1a and 3a, to give 2a and 4a, do not result in any significant changes in the molecular conformations. Each of the four molecular conformations possesses a ZC(O)NR/E(C=N) arrangement about the C(O)–NR–N=C(H, aryl) fragment (R=H or Me). The dominant intermolecular interactions in 1a and 3a are N–H···O(carbonyl) hydrogen bonds, with other intermolecular interactions being weaker interactions: C–H···O and N–O···π in 1a and C–H···X (X=O, S, π) and π–π interactions in 3a. In the N-methylated compounds, the intermolecular interactions are restricted to weaker C–H···O hydrogen bonds in 2a and C–H···X (X=O or π) interactions in 4a.
Keywords: acyl hydrazones; crystal structures; thienyl derivativesDocument Type: Research ArticleDOI: http://dx.doi.org/10.1515/zkri-2015-1902Publication date: 1 de Março de 2016

Compartilhar publicação

Facebook
Twitter
Email
LinkedIn
WhatsApp

Deixe seu comentário

Compartilhar

Sobre a SSCDT

Nosso grupo de pesquisa está situado em Farmanguinhos e atualmente é o maior laboratório farmacêutico oficial vinculado ao Ministério da Saúde. Farmanguinhos produz mais de um bilhão de medicamentos por ano para os programas estratégicos do Governo Federal, além de atender demandas emergenciais no Brasil e no exterior.

posts Recentes