[anilin]

I would like to know in the salt formation of ergometrine compound which of the nitrogen atoms is involved in the salt formation and why?
Thanks

[Dolphinsiu]

This is not a difficult problem. Salt is formed by amide linkage which is implied by neutralization reaction of carboxylic acid (acid) and amine (base). Hence, obviously, the nitrogen atom not in ring structure is the most probably party involved in salt formation.

[dielsalder]

from my point of view i would say that the salt would be created with the cyclic nitrogen (n-methyl)

the nitrogen from the indol ring is not basic since it participate to the aromaticity of the indole
the amide .. well i don't know but if you compared to the lsd molecule im pretty shure the salt is not on the diethylamide

[anilin]

from my point of view i would say that the salt would be created with the cyclic nitrogen (n-methyl)

the nitrogen from the indol ring is not basic since it participate to the aromaticity of the indole
the amide .. well i don't know but if you compared to the lsd molecule im pretty shure the salt is not on the diethylamide

thanks but I cannot see any +ive ion attached to the cyclic nitrogen (n-methyl) apart from the methyl.  Lsd and ergometrine both have this methyl group. what is the role of maleic acid?
By the way, how do you paste an image (i.e. the Lsd structure) to your messages?

[dielsalder]

you cannot make a simple HCl salt in this molecule. The HCl could react somewhere esle in the molecule and could ruin you syntesis

you need to make a tartrate salt ...insted of HCl you use tartrate acid




with tartrate salt your molecule is watersoluble and can be stored in distilled water (not chlorinated water) in your fridge for ..well your lifetime

go to imageshack.us and you can upload your image and its gonna give you an URL of your picture

[anilin]

you cannot make a simple HCl salt in this molecule. The HCl could react somewhere esle in the molecule and could ruin you syntesis

you need to make a tartrate salt ...insted of HCl you use tartrate acid




with tartrate salt your molecule is watersoluble and can be stored in distilled water (not chlorinated water) in your fridge for ..well your lifetime

go to imageshack.us and you can upload your image and its gonna give you an URL of your picture

I am still not sure why this salt formation occurs on the N in the ring not in the peptide link. would you explain that a little more?
Thanks