The analysis of the proton magnetic resonance spectra of heteroaromatic systems. IV. Benzofuran, indole, and related compounds

1965 ◽  
Vol 18 (3) ◽  
pp. 353 ◽  
Author(s):  
PJ Black ◽  
ML Heffernan
Keyword(s):  
Magnetic Resonance ◽  
Proton Magnetic Resonance ◽  
Coupling Constants ◽  
Spectral Parameters ◽  
Related Compounds ◽  
Magnetic Resonance Spectra

The proton magnetic resonance spectra of benzofuran, dibenzofuran, indole, 7-azaindole, carbazole, and 4-azacarbazole (α-carboline) have been investigated at 100 Mc/s, and the spectral parameters for these molecules have been obtained. The presence of cross-ring coupling constants involving the NH proton of indole and carbazole is reported.

Protonenresonanz-Spektroskopie ungesättigter Ringsysteme I

1965 ◽  
Vol 20 (10) ◽  
pp. 948-956 ◽  
Author(s):  
Harald Günther
Keyword(s):  
Magnetic Resonance ◽  
Concentration Dependence ◽  
Proton Magnetic Resonance ◽  
Chemical Shifts ◽  
Electron System ◽  
Coupling Constants ◽  
Resonance Signal ◽  
Aromatic Character ◽  
Additional Support ◽  
Magnetic Resonance Spectra

The proton magnetic resonance spectra of 1.6-methano- and 1.6-oxido-cyclodecapentaene are described and analyzed in terms of chemical shifts and coupling constants. The results are discussed in connection with the structure and possible aromatic character of these compounds. Measurements of the concentration dependence of the chloroform resonance signal in solutions of both compounds give additional support for the presence of a delocalized 10 π-electron system.

The analysis of the proton magnetic resonance spectra of heteroaromatic systems. V. Diazanaphthalenes

1965 ◽  
Vol 18 (5) ◽  
pp. 707 ◽  
Author(s):  
PJ Black ◽  
ML Heffernan
Keyword(s):  
Carbon Tetrachloride ◽  
Magnetic Resonance ◽  
Long Range ◽  
Iterative Procedure ◽  
Proton Magnetic Resonance ◽  
Chemical Shifts ◽  
Direct Calculation ◽  
Coupling Constants ◽  
Dilute Solutions ◽  
Magnetic Resonance Spectra

The proton magnetic resonance spectra of the four isomeric diazanaphthalenes, quinoxaline, phthalazine, quinazoline, and cinnoline, all as dilute solutions in carbon tetrachloride and acetone, have been investigated at 100 Mc/s. The chemical shifts and coupling constants have been obtained by direct calculation or, where appropriate, by an iterative procedure. Long-range coupling constants between protons separated by five and six bonds have been observed.

Aza-analogues of pteridine. III. Some monomethoxy-1,2,4,6,8-pentaazanaphthalenes and related compounds

1971 ◽  
Vol 24 (3) ◽  
pp. 633 ◽  
Author(s):  
DJ Brown ◽  
T Sugimoto
Keyword(s):  
Magnetic Resonance ◽  
Proton Magnetic Resonance ◽  
Triethyl Orthoformate ◽  
Ionization Constants ◽  
Reductive Cyclization ◽  
Ultraviolet Spectra ◽  
Chloro Derivative ◽  
Related Compounds ◽  
Magnetic Resonance Spectra

4-Hydrazino-2-methoxy-6-methyl-5-nitropyrimidine reacted with triethyl orthoformate to give the ethoxymethylenehydrazino analogue or 4-methoxy-6-methyl-7-nitro-1,2,3a,5-tetraazaindene according to conditions. The first of these products was converted by reductive cyclization and subsequent dehydrogenation into 7-methoxy-5-methyl- 1,2,4,6,8-pentaazanaphthalene. Attempts to hydrolyse this and related compounds to the corresponding 7-hydroxypentaazanaphthalenes failed and direct approaches via appropriate 2-hydroxypyrimidines gave only 4- hydroxy-7-nitrotetraazaindenes. ��� 5-Alkoxypentaazanaphthalenes were prepared via 1,2-dihydropentaaza- naphthalene or its 5-chloro derivative. Nucleophilic displacements were used to make the 5-hydroxy, 5-methylthio, 5-diethylamino, and other analogues from 5-methoxy-3-methylpentaazanaphthalene. ��� The ionization constants, ultraviolet spectra, and proton magnetic resonance spectra of members of both bicyclic series are tabulated and discussed.

Infrared, Raman, and proton magnetic resonance spectra of dicyclopentadienylmercury and related compounds

1969 ◽  
Vol 8 (5) ◽  
pp. 1108-1113 ◽  
Author(s):  
E. Maslowsky ◽  
Kazuo Nakamoto
Keyword(s):  
Magnetic Resonance ◽  
Proton Magnetic Resonance ◽  
Related Compounds ◽  
Magnetic Resonance Spectra

Proton magnetic resonance spectra of indolizine and its methyl derivatives and aza analogues

1964 ◽  
Vol 17 (10) ◽  
pp. 1128 ◽  
Author(s):  
PJ Black ◽  
ML Heffernan ◽  
LM Jackman ◽  
QN Porter ◽  
GR Underwood
Keyword(s):  
Magnetic Resonance ◽  
Long Range ◽  
Iterative Procedure ◽  
Proton Magnetic Resonance ◽  
Chemical Shifts ◽  
Coupling Constants ◽  
Methyl Derivatives ◽  
Magnetic Resonance Spectra

The proton magnetic resonance spectra of indolizine, indolizine-1,3-d2, 1- and 2-methylindolizine, 2,3-, 2,5-, 2,6-, and 2,7-dimethylindolizine and 1-, 2-, and 3-azaindolizine have been determined at 100 and/or 60 Mc/s. Unequivocal assignments have been made to all protons and the coupling constants and chemical shifts for indolizine and its aza analogues have been obtained by an iterative procedure. Long-range coupling constants involving protons separated by five and six bonds have been observed.

REACTIONS OF AMIDES AND RELATED COMPOUNDS: III. N.M.R. INVESTIGATION OF THE PROTONATION OF N,N-DIMETHYLNITROSOAMINE, N,N-DIETHYLNITROSOAMINE, AND N-NITROSOPIPERIDINE

1966 ◽  
Vol 44 (2) ◽  
pp. 105-109 ◽  
Author(s):  
Stephen J. Kuhn ◽  
John S. McIntyre
Keyword(s):  
Sulfuric Acid ◽  
Magnetic Resonance ◽  
Perchloric Acid ◽  
Trifluoroacetic Acid ◽  
Proton Magnetic Resonance ◽  
Acid Solutions ◽  
Concentrated Sulfuric Acid ◽  
Related Compounds ◽  
Equimolar Solution ◽  
Magnetic Resonance Spectra

Protonation of N,N-dimethylnitrosoamine has been investigated by dissolving the nitrosoamine in different acids and recording the proton magnetic resonance spectra of these solutions. Concentrated sulfuric acid, sulfuric acid monohydrate, perchloric acid (72%), trifluoroacetic acid, and fluorosulfuric acid have been used in this study. Only in fluorosulfuric acid near 0 °C and lower was a new signal observed for the protonated nitrosoamine molecule. Integration of the peaks has shown that only one proton is captured by the nitrosoamine. The following structure is suggested for the protonated nitrosoamine.[Formula: see text]The n.m.r. spectra of fluorosulfuric acid solutions of N,N-diethylnitrosoamine and N-nitrosopiperidine also show separate signals for the captured proton.The n.m.r. spectrum of an equimolar solution of N,N-dimethylnitrosoamine, N,N-dimethylformamide, and trifluoroacetic acid in 2-nitropropane indicates that N,N-dimethylnitrosoamine is a weaker base.

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