Reductive Activation of Arenes. Part 17. Effect of Methyl Substituent in Anion-Radicals of Tolunitriles on the Mechanism of Their Reaction with Alkyl Bromides in Liquid Ammonia.

ChemInform ◽  
2005 ◽  
Vol 36 (1) ◽  
Author(s):  
T. A. Vaganova ◽  
V. D. Shteingarts
Keyword(s):  
Liquid Ammonia ◽  
Methyl Substituent ◽  
Reductive Activation ◽  
Alkyl Bromides ◽  
Anion Radicals

scholarly journals Effect of methyl substituent on the solubility of 1,4-benzoquinone derivatives in n-octanol/water system

2020 ◽  
Vol 23 (5) ◽  
pp. 142-146
Author(s):  
Siti Mariyah Ulfa ◽  
Fath Dwisari ◽  
Ade Cintyia Sally ◽  
Mohammad Farid Rahman
Keyword(s):  
Shake Flask ◽  
Water System ◽  
Insertion Reaction ◽  
Log P ◽  
Methyl Substituent ◽  
Promising Candidate ◽  
New Drug ◽  
Alkyl Bromides ◽  
Ft Ir ◽  
Uv Visible

The solubility of the compound is a crucial task for new drug design. Quinone is a promising candidate to develop as a new drug. In this research, the synthesis of 1,4-benzoquinone derivatives, that is, 2-(5-bromoamyl)-3,5-dimethyl-1,4-benzoquinone (2a) and 2-(5-bromoamyl)-5-methyl-1,4-benzoquinone (2b) were carried out by decarboxylation and insertion reaction of alkyl bromides. The product 2a and 2b are purified using SiO2 gel column chromatography and analyzed by UV-Visible, FT-IR, and NMR. The yield of 2a is 13.75%, and 2b is 4.04%. The solubility of 2a and 2b, expressed by log P, is measured in the n-octanol/water (3:7 (v/v)) system by the shake flask method. The log P of 2a and 2b are 2.99 and 1.36, respectively. It is showed that the log P of 2a is higher compared to 2b. The presence of two methyl substituents on the quinone ring of 2a supports the increase of hydrophobicity of the compound in the n-octanol/water system.

Reductive activation of arenes. VII. Alkylation of 9-cyanoanthracene two-electron reduction products in liquid ammonia.

Tetrahedron ◽  
1994 ◽  
Vol 50 (33) ◽  
pp. 10011-10020 ◽  
Author(s):  
Tamara A. Vaganova ◽  
Elena V. Panteleeva ◽  
Andrej P. Tananakin ◽  
Vitalij D. Shteingarts ◽  
Itzhak I. Bilkis
Keyword(s):  
Liquid Ammonia ◽  
Reductive Activation ◽  
Electron Reduction
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