Hydrazones from hydroxy naphthaldehydes and N-aminoheterocycles: structure and stereodynamics |
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Authors: | R Fernando Martínez Martín ÁvalosReyes Babiano Pedro CintasMark E Light José L JiménezJuan C Palacios Esther MS PérezVicenta Rastrojo |
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Institution: | a Departamento de Química Orgánica e Inorgánica, QUOREX Research Group, Universidad de Extremadura, Avda. Elvas s/n, E-06006 Badajoz, Spain b Department of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UK |
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Abstract: | Schiff bases derived from 2-hydroxy-1-naphthaldehyde, or 1-hydroxy-2-naphthaldehyde, and different saturated N-aminoheterocycles have been prepared. Their structures have been elucidated in both solution and the solid state, including unequivocal X-ray diffraction analyses. Experimental data evidence the presence of imine (or hydrazone) structures as the most stable tautomers, while all attempts to switch to enamine (or enhydrazine) structures based on electronic and steric considerations were unsuccessful. A complete conformational analysis assisted by DFT calculations at B3LYP/6-31G∗ and M06-2X/6-311++G∗∗ levels has been performed on each series of representative structures. |
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Keywords: | Imine-enamine tautomerism Conformational analysis Hidrazones |
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