joniaguis - 8-5-2009 at 13:52
Fluvastatin is a strong acid while its salt is a weak base. It loses the H ion more readily due to the negative inductive effects of the O atoms and F
atom.
Is this statement correct? Does the F atom, although it is the most electronegative atom, has a significant role due to its distance from the COOH
bond?
DJF90 - 8-5-2009 at 14:07
This should be in the beginnings section. It would be appreciated if you attached a picture of the molecule so we can see what you're talking about. I
dont think this statement is correct. Wikipedia shows the structure of Fluvastatin here:
http://en.wikipedia.org/wiki/Fluvastatin
If this is to beleived to be the correct structure, then depending on how you form the salt will depend on the compounds characteristics:
> Using acid, you form a salt by protonating the tertiary amine. Then the ammonium cation is itself acidic, and the carboxylate is also (more)
acidic.
> Using base, you form a salt by deprotonating the carboxylic acid. Then the carboxylate cation is (weakly) basic, and the tertiary amine is also
basic.
The alcohol oxygens only have a mild effect on the acidity of the carboxylic acid. I expect the fluorine to have very little to no effect due to its
sheer distance from the carboxylic acid group.
joniaguis - 8-5-2009 at 14:15
yep thats fluvastatin. The N is a weak base though here since its lone pair is delocalised. therefore fluvastatin is a weak base
DJF90 - 8-5-2009 at 14:17
Yes I missed the delocalisation. If you know the answer then why bother asking?
Also I made a mistake. This should be in the short questions thread in the "miscellaneous" forum. This does not need a whole thread devoted to it.
[Edited on 8-5-2009 by DJF90]
joniaguis - 8-5-2009 at 14:19
I just want to make sure that the answer is perfectly correct. don't want flaws in my answers. 