Preparation and molecular structures of N′-(2-heteroarylmethylidene)-3-(3-pyridyl)acrylohydrazides
-
Karolina Jasiak
,
Bartosz Zarychta
Abstract
The crystal and molecular structures of N′-(2-furylmethylidene)-3-(3-pyridyl)acrylohydrazide and N′-(2-thienylmethylidene)-3-(3-pyridyl)acrylohydrazide are reported, and the influence of the type of the heteroatom on the aromaticity of the aromatic rings is discussed. Both molecules are nearly planar. The geometry of the acrylohydrazide arrangement is comparable to that of homologous compounds. Density functional theory (DFT) calculations were performed in order to analyze the changes in the geometry of the studied compounds in the crystalline state and for the isolated molecule. The most significant changes were observed in the values of the N–N and C–N bond lengths. The harmonic oscillator model of aromaticity index, calculated for the furan and thiophene rings, demonstrated a noticeable increase in aromaticity in comparison to isolated rings and their DFT-calculated structures. By contrast, the nucleus independent chemical shift index indicated a decrease in aromatic character of the rings containing heteroatoms.
Acknowledgments
The authors are thankful for calculation facilities and software. Calculations have been carried out in the Wroclaw Centre for Networking and Supercomputing (http://www.wcss.pl), grant no. 311.
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Articles in the same Issue
- Frontmatter
- In this Issue
- Analysis of two [2]catenanes based on electron densities from invariom refinement and results from DFT calculations
- Orthoamide und Iminiumsalze, XCVa. Umsetzungen von Orthoamiden von Alkin-Carbonsäuren mit Acetophenonen und Acetophenon-Phenylhydrazonen
- Metal-free, air-promoted, radical-mediated arylation of benzoquinone with phenylhydrazines
- Three-component condensation reaction of various aldehydes, dimedone and malononitrile catalyzed by boric acid in water in comparison with multifunctional ionic liquids as green catalytic systems
- Synthesis, characterization, and electrochemical study of a mononuclear Cu(II) complex with a 4-acyl pyrazolone ligand
- Synthesis of LaCoO3 powder by a combined mechanical/thermal process
- Preparation and molecular structures of N′-(2-heteroarylmethylidene)-3-(3-pyridyl)acrylohydrazides
- A new modification of [Ag4Br4(PPh3)4]: synthesis, structure and properties
- Magnetic and magnetocaloric properties of the coloured Heusler phases GdAg2Mg and REAgAuMg (RE=Gd, Tb, Dy)
