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Analysis of ethyl (2 E )-3-(4-hydroxy-3,5-dimethoxyphenyl) prop-2-enoate

2011; Wiley; Volume: 67; Issue: a1 Linguagem: Inglês

10.1107/s0108767311083097

1600-5724

C. Lariucci, L. Malaspin, Wren Austin Fernandes, Joaquim Mendes da Silva, Gilberto L. B. Aquino, H. C. A. S. Napolitano,

Chemical Synthesis and Analysis

SessionsC668 primary hydrogen bond backbone; Fpm_N with N-H…N and Fpm_ O with N-H…O=C as primary interaction.The Fom isomer was unexpectedly found highly disordered with Z' = 6.The most significant structural characteristic of the Fxo triad was formation of twisted dimmers trough double N...H-N hydrogen bonding creating centrosymmetric R 2 2 (8) rings.Formation of dimmers when pyridine nitrogen is in ortho position is already seen in analogue Mxo [2] isomers.Computational modelling and conformational analyses of the Fxx isomers and their comparison with solid state structures showed that modelled structures generally comply with solid state conformations except in the Fxm isomers.Modelling of the Fox isomer triad suggested existence of intramolecular F...H-N bonding.Spectroscopic and crystallographic data supported this prediction.This work represents the final step in the investigation of the four benzamide/carboxamide isomer grids with methyl/fluorine substituents (Mxx [1] , NxxF [2], NxxM [3] and Fxx), by both solid state methods and computational modelling, with innovative approach in bridging two powerful structural methods together.The comparison of the four isomer grids revealed high degree of similarity regarding solid state aggregation and physicochemical properties, while correlated melting point values indicated significance of the substituent position on thermal behaviour, rather than the nature of substituent.