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Answer to Question #59013 in Organic Chemistry for sahar

Question #59013
chloroazodin
this compound has Nitrogen groups and can be charged for hydrogen bond in water according to the structure,so i have question why chloroazodin cant be dissolve in water?
Thanks.
Expert's answer
There are 2 key points to explain low dissolvance of the chloroazodin in the water. First point is that molecule has it's own strong condenced structure ( something likemolecule of benzene). Electronic density is shifted to the centre of the molecule - N=N- azobond. The second point is that amine groups have strong electrofilic substituents - chlorine atoms, thus they can not react with the water molecules due to the strong electronic shift. Likewise the chloroamine groups, H atoms of the imido group C=N-H, can not react with the water molecules owing the double = bond. All mentioned above results in the low solubility of the chloroazodine molecule in the water.

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