Crystal structures of 2-[5-nitrothien-2-yl)- CH=N–NR–CO(CH2)n]thiophene compounds (R = H or Me; n = 0 or 1)
Author:
Cardoso Laura N.F., Noguiera Thais C.M.1, Kaiser Carlos R.2, Wardell James L., Wardell Solange M.S.V.3, de Souza Marcus V.N.
Affiliation:
1. Fundação Oswaldo Cruz, Instituto de Tecnologia em Fármacos-Far Manguinhos, Manguinhos, 21041-250, Rio de Janeiro, Brazil 2. Instituto de Química, Universidade Federal do Rio de Janeiro, Cidade Universitária, 21945-970, Rio de Janeiro, Brazil 3. CHEMSOL 1 Harcourt Road, Aberdeen, AB15 5NY, Scotland
Abstract
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 Z
C(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.
Publisher
Walter de Gruyter GmbH
Subject
Inorganic Chemistry,Condensed Matter Physics,General Materials Science
Reference30 articles.
1. I. E. Perepichka, D. F. Perepicka, Eds, Handbook of Thiophene-Based Materials: Applications in Organic Electronics and Photonics, 2 Volume Set, Wiley, UK, 2009. 2. L. Chan, O. Pereira, T. J. Reddy, K. D. Sanjov, C. Possion, M. Courchesne, M. Proulx, A. Siddiqui, C. G. Yannopoulos, Discovery of thiophene-2-carboxylic acids as potent inhibitors of HCV NS5B polymerase and HCV subgenomic RNA replication. Part 2: Tertiary amides. Bioorg. Med. Chem. Lett.2004, 14, 797. 3. R. Romagnoli, P. G. Baraldi, P. Cruz-Lopez, M. Tolomeo, A. Di Cristina, R. M. Pipitone, S. Grimaudo, J. Balzarini, A. Brancale, E. Hamei, Synthesis of novel antimitotic agents based on 2-amino-3-aroyl-5-(hetero)arylethynyl thiophene derivatives. Bioorg. Med. Chem. Lett.2011, 21, 2746. 4. A. Sivadas, M. P. Satyaseela, T. Bharani, S. K. Upparapalli, N. Subbarava, Design, Synthesis, Characterization and antibacterial activity of methyl -2-(mercaptomethyl)-3-(2-thienyl) acrylate. Int. J. Pharm. Sci. Res.2011, 2, 27. 5. S. Jain, N. Babu, S. R. Jatti, H. Sahah, S. P. Dhaneira, Synthesis, antitubercular and antifungal activities of heteroaryl-substituted oxiranes derived from Baylis–Hillman adducts. Med. Chem. Res.2012, 21, 2744.
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