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Abstract:

The 1 H and 13 C NMR spectra of 3‐nitro‐, 5‐nitro‐ and 3,5‐dinitro‐2‐methoxypyridines have been determined. The results show the preferred cis conformation for the 2‐methoxy group, and the importance of steric repulsion between the oxygen atom of this group and those of the o‐nitro group which hinders conjugation in the 3‐nitro‐substituted derivatives. Similar steric inhibition of resonance is observable with 2‐N‐butylamine‐, 2‐N‐cyclohexylamine‐ and 2‐(N‐piperidyl)‐substituted nitropyridines, whose 1 H and 13 C NMR spectra were also determined. In the case of the secondary amines, a hydrogen bond between the amino proton and the 3‐nitro group was clearly detected. 1 H and 13 C NMR spectra of 2,6‐dinitro‐, 2,4‐dinitro‐ and 2,4,6‐trinitro‐2‐R‐benzenes (R = OCH 3 , NHC 4 H 9 , NH‐cyclo‐C 6 H 11 , NC 5 H 10 ) were also recorded and compared with those of the pyridine derivatives. The electronic aza and nitro group effects are comparable if conjugation of the nitro group is not hindered. Copyright © 1986 John Wiley & Sons, Ltd.

Registro:

Documento: Artículo
Título:1 H and 13 C NMR studies of substituted nitropyridines and nitrobenzenes
Autor:Nudelman, N.S.; Cerdeira, S.B.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas Y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón II, P. 3, Buenos Aires, 1428, Argentina
Palabras clave:1 H and 13 C NMR; Conformation MS; Hydrogen bonding; Nitrobenzenes; Nitropyridines
Año:1986
Volumen:24
Número:6
Página de inicio:507
Página de fin:511
DOI: http://dx.doi.org/10.1002/mrc.1260240607
Título revista:Magnetic Resonance in Chemistry
Título revista abreviado:Magn. Reson. Chem.
ISSN:07491581
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_07491581_v24_n6_p507_Nudelman

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Citas:

---------- APA ----------
Nudelman, N.S. & Cerdeira, S.B. (1986) . 1 H and 13 C NMR studies of substituted nitropyridines and nitrobenzenes. Magnetic Resonance in Chemistry, 24(6), 507-511.
http://dx.doi.org/10.1002/mrc.1260240607
---------- CHICAGO ----------
Nudelman, N.S., Cerdeira, S.B. "1 H and 13 C NMR studies of substituted nitropyridines and nitrobenzenes" . Magnetic Resonance in Chemistry 24, no. 6 (1986) : 507-511.
http://dx.doi.org/10.1002/mrc.1260240607
---------- MLA ----------
Nudelman, N.S., Cerdeira, S.B. "1 H and 13 C NMR studies of substituted nitropyridines and nitrobenzenes" . Magnetic Resonance in Chemistry, vol. 24, no. 6, 1986, pp. 507-511.
http://dx.doi.org/10.1002/mrc.1260240607
---------- VANCOUVER ----------
Nudelman, N.S., Cerdeira, S.B. 1 H and 13 C NMR studies of substituted nitropyridines and nitrobenzenes. Magn. Reson. Chem. 1986;24(6):507-511.
http://dx.doi.org/10.1002/mrc.1260240607