NMR and DFT investigations of the substituent and solvent effect on amino-imino tautomerism in acridin-9-amines substituted at the exocyclic nitrogen atom

2005 ◽  
Vol 18 (8) ◽  
pp. 870-879 ◽  
Author(s):  
Youssif Ebead ◽  
Agnieszka Wróblewska ◽  
Karol Krzymiński ◽  
Janusz Rak ◽  
Jerzy Błażejowski
1983 ◽  
Vol 36 (5) ◽  
pp. 1031 ◽  
Author(s):  
TJ Broxton ◽  
MJ Mcleish

A comparison of the relative amounts of dediazoniation, SNAr and aryne reactions of 4-chloro-3- nitrobenzenediazonium ion with methoxide ion in CH3OH and in CD3OH confirms that the dediazoniation reaction involves hydride abstraction from the alkoxide ion by the electrophilic terminal nitrogen atom of the diazonium ion. Furthermore, the relative amounts of anionic and free-radical dediazoniation are the same in CH3OH and in CD3OH. This confirms that the partitioning between the free-radical and anionic pathways for dediazoniation is on the aryl diimide and not on the free diazonium ion. Some previously reported results on the solvent effect (methanol against ethanol) for the reaction have been reinterpreted in the light of the above conclusions.


Tetrahedron ◽  
2013 ◽  
Vol 69 (3) ◽  
pp. 1217-1228 ◽  
Author(s):  
Viktor O. Iaroshenko ◽  
Marcelo Vilches-Herrera ◽  
Ashot Gevorgyan ◽  
Satenik Mkrtchyan ◽  
Knar Arakelyan ◽  
...  

1984 ◽  
Vol 62 (11) ◽  
pp. 2186-2191 ◽  
Author(s):  
Marie-Rose Marre ◽  
Michel Sanchez ◽  
Robert Wolf ◽  
Joël Jaud ◽  
Jean Galy

Iminodiazophospholane 1 was obtained as monoclinic crystals, space group P21/c with a = 10.243(9), b = 17.236(5), c = 11.992(9) Å, and Z = 4. The structure was determined by single-crystal X-ray diffraction and was refined up to R = 0.056[Formula: see text]for 1342 reflections. The geometry of the molecule is that of a distorted tetrahedron with [Formula: see text] angles varying from 91.8° (ring angle) to 121.7° for [Formula: see text]. The diazophospholane ring has an envelope conformation where one of the 2 carbon atoms is at the tip. The three tricoordinated nitrogen atoms have a planar structure; the lone pairs on the two ring nitrogens have parallel orientation and both are orthogonal to the lone pair of the exocyclic nitrogen atom (N7). The P—N bond lengths are relatively short, falling between 1.620 Å and 1.669 Å, while the P2=N6 bond of 1.539 Å is among the smallest values ever reported. The multiplicities of the P—N bonds were assigned on the basis of an empirical method: 0.10 for the two cyclic P—N, 0.25 for the exocyclic P—N, and 0.60 for [Formula: see text] [Journal translation]


2004 ◽  
Vol 303 (3) ◽  
pp. 301-308 ◽  
Author(s):  
Agnieszka Wróblewska ◽  
Joanna Meszko ◽  
Karol Krzymiński ◽  
Youssif Ebead ◽  
Jerzy Błażejowski

2016 ◽  
Vol 12 ◽  
pp. 2563-2569 ◽  
Author(s):  
Alena S Pankova ◽  
Pavel R Golubev ◽  
Alexander F Khlebnikov ◽  
Alexander Yu Ivanov ◽  
Mikhail A Kuznetsov

2-(Alkyl(aryl)amino)thiazol-4(5H)-ones can regioselectively be prepared from monoalkyl(aryl)thioureas and maleimides. In solution, the former heterocycles exist in a tautomeric equilibrium with 2-(alkyl(aryl)imino)thiazolidin-4-ones and the substituent on the exocyclic nitrogen atom governs the ratio of these tautomers. Isomers with the alkyl group in the endocyclic position can be obtained from N-methyl(ethyl)thioureas. 2D NMR spectroscopy and DFT calculations rationalize experimental results.


2007 ◽  
Vol 66 (4-5) ◽  
pp. 1016-1023 ◽  
Author(s):  
Youssif Ebead ◽  
Alexander D. Roshal ◽  
Agnieszka Wróblewska ◽  
Andrey O. Doroshenko ◽  
Jerzy Błażejowski

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