1 H and 13 C NMR studies of substituted nitropyridines and nitrobenzenes

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 hinde...

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Detalles Bibliográficos
Autor principal: Cerdeira, Silvia Beatriz
Publicado: 1986
Materias:
1 H and 13 C NMR
Conformation MS
Hydrogen bonding
Nitrobenzenes
Nitropyridines
Acceso en línea:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_07491581_v24_n6_p507_Nudelman
http://hdl.handle.net/20.500.12110/paper_07491581_v24_n6_p507_Nudelman
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id paper:paper_07491581_v24_n6_p507_Nudelman
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spelling paper:paper_07491581_v24_n6_p507_Nudelman2023-06-08T15:45:26Z 1 H and 13 C NMR studies of substituted nitropyridines and nitrobenzenes Cerdeira, Silvia Beatriz 1 H and 13 C NMR Conformation MS Hydrogen bonding Nitrobenzenes Nitropyridines 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. Fil:Cerdeira, S.B. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 1986 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_07491581_v24_n6_p507_Nudelman http://hdl.handle.net/20.500.12110/paper_07491581_v24_n6_p507_Nudelman
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic 1 H and 13 C NMR
Conformation MS
Hydrogen bonding
Nitrobenzenes
Nitropyridines
spellingShingle 1 H and 13 C NMR
Conformation MS
Hydrogen bonding
Nitrobenzenes
Nitropyridines
Cerdeira, Silvia Beatriz
1 H and 13 C NMR studies of substituted nitropyridines and nitrobenzenes
topic_facet 1 H and 13 C NMR
Conformation MS
Hydrogen bonding
Nitrobenzenes
Nitropyridines
description 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.
author Cerdeira, Silvia Beatriz
author_facet Cerdeira, Silvia Beatriz
author_sort Cerdeira, Silvia Beatriz
title 1 H and 13 C NMR studies of substituted nitropyridines and nitrobenzenes
title_short 1 H and 13 C NMR studies of substituted nitropyridines and nitrobenzenes
title_full 1 H and 13 C NMR studies of substituted nitropyridines and nitrobenzenes
title_fullStr 1 H and 13 C NMR studies of substituted nitropyridines and nitrobenzenes
title_full_unstemmed 1 H and 13 C NMR studies of substituted nitropyridines and nitrobenzenes
title_sort 1 h and 13 c nmr studies of substituted nitropyridines and nitrobenzenes
publishDate 1986
url https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_07491581_v24_n6_p507_Nudelman
http://hdl.handle.net/20.500.12110/paper_07491581_v24_n6_p507_Nudelman
work_keys_str_mv AT cerdeirasilviabeatriz 1hand13cnmrstudiesofsubstitutednitropyridinesandnitrobenzenes
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