Hydrazones from hydroxy naphthaldehydes and N-aminoheterocycles: structure and stereodynamics
Hydrazones from hydroxy naphthaldehydes and N-aminoheterocycles: structure and stereodynamics
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.
imine–enamine tautomerism, conformational analysis, hidrazones
2025-2034
Martínez, R. Fernando
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Ávalos, Martín
2d0b39c7-15a3-4f90-bdfb-8e4b6e69c64a
Babiano, Reyes
b7ffd91c-bacd-4372-ab99-fc30ac2450ae
Cintas, Pedro
29979233-8382-47a8-bde7-1faf4869308c
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Jiménez, José L.
074cc8fd-9ea1-41fc-b8b6-551d26e5fcd3
Palacios, Juan C.
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Pérez, Esther M.S.
ef821a32-3f5b-4a33-a123-f6adf462a26e
Rastrojo, Vicenta
c78d434c-25bb-4742-b31c-15d37c04b618
11 March 2011
Martínez, R. Fernando
25456861-d6d7-4964-ac9c-54f5a1e5c2ba
Ávalos, Martín
2d0b39c7-15a3-4f90-bdfb-8e4b6e69c64a
Babiano, Reyes
b7ffd91c-bacd-4372-ab99-fc30ac2450ae
Cintas, Pedro
29979233-8382-47a8-bde7-1faf4869308c
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Jiménez, José L.
074cc8fd-9ea1-41fc-b8b6-551d26e5fcd3
Palacios, Juan C.
2c06e379-89b3-46b1-95c8-7f5057732f9f
Pérez, Esther M.S.
ef821a32-3f5b-4a33-a123-f6adf462a26e
Rastrojo, Vicenta
c78d434c-25bb-4742-b31c-15d37c04b618
Martínez, R. Fernando, Ávalos, Martín, Babiano, Reyes, Cintas, Pedro, Light, Mark E., Jiménez, José L., Palacios, Juan C., Pérez, Esther M.S. and Rastrojo, Vicenta
(2011)
Hydrazones from hydroxy naphthaldehydes and N-aminoheterocycles: structure and stereodynamics.
Tetrahedron, 67 (11), .
(doi:10.1016/j.tet.2011.01.065).
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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Accepted/In Press date: 22 January 2011
e-pub ahead of print date: 28 January 2011
Published date: 11 March 2011
Keywords:
imine–enamine tautomerism, conformational analysis, hidrazones
Identifiers
Local EPrints ID: 385752
URI: http://eprints.soton.ac.uk/id/eprint/385752
ISSN: 0040-4020
PURE UUID: cb62e83b-8dd8-4382-a853-ec11864667b4
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Date deposited: 21 Jan 2016 16:27
Last modified: 15 Mar 2024 03:01
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Contributors
Author:
R. Fernando Martínez
Author:
Martín Ávalos
Author:
Reyes Babiano
Author:
Pedro Cintas
Author:
José L. Jiménez
Author:
Juan C. Palacios
Author:
Esther M.S. Pérez
Author:
Vicenta Rastrojo
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