Home >
Community >
Are N-oxides stable in aqueous alkaline solution?
Upvote
VOTE
Downvote
+ Organic
Posted by
Mike Jones
Are N-oxides stable in aqueous alkaline solution?
Re posters original question. I'd expect the N-oxides to be reasonably stable. If pyridine-N-oxide were dissolved in water and made basic, I wouldn't expect anything to happen. Did something happen?
Re posters original question. I'd expect the N-oxides to be reasonably stable. If pyridine-N-oxide were dissolved in water and made basic, I wouldn't expect anything to happen. Did something happen?
I guess another sensible question to ask is what would happen in acidic solutions? My guess would be that the oxygen would be protonated and become a leaving group, leaving you with, for example, just pyridine.
So I guess it depends how alkaline your solution is? The more H+ available the less stable the compounds.
Seems logical to me anyway but I guess this would explain why there there's no obvious straightforward answer: It depends on the pH of your solution.
I guess another sensible question to ask is what would happen in acidic solutions? My guess would be that the oxygen would be protonated and become a leaving group, leaving you with, for example, just pyridine.
So I guess it depends how alkaline your solution is? The more H+ available the less stable the compounds.
Seems logical to me anyway but I guess this would explain why there there's no obvious straightforward answer: It depends on the pH of your solution.
My guess would be that the oxygen would be protonated and become a leaving group, leaving you with, for example, just pyridine.
No, that would give you Py2+, which won't happen. To get pyridine from pyridinium N-oxide you need nucleophilic abstraction of O - i.e. the Py is the leaving group, not hydroxide/water.
I'd guess that SNAr reactions (for example with hydroxide: pyridine N-oxide 2-pyridone) would be a more likely degradation pathway - but I don't know the answer to the OP's question.
My guess would be that the oxygen would be protonated and become a leaving group, leaving you with, for example, just pyridine.
No, that would give you Py2+, which won't happen. To get pyridine from pyridinium N-oxide you need nucleophilic abstraction of O - i.e. the Py is the leaving group, not hydroxide/water.
I'd guess that SNAr reactions (for example with hydroxide: pyridine N-oxide 2-pyridone) would be a more likely degradation pathway - but I don't know the answer to the OP's question.
More
VOTE
So I guess it depends how alkaline your solution is? The more H+ available the less stable the compounds.
Seems logical to me anyway but I guess this would explain why there there's no obvious straightforward answer: It depends on the pH of your solution.
So I guess it depends how alkaline your solution is? The more H+ available the less stable the compounds.
Seems logical to me anyway but I guess this would explain why there there's no obvious straightforward answer: It depends on the pH of your solution.
More
VOTE
No, that would give you Py2+, which won't happen. To get pyridine from pyridinium N-oxide you need nucleophilic abstraction of O - i.e. the Py is the leaving group, not hydroxide/water.
I'd guess that SNAr reactions (for example with hydroxide: pyridine N-oxide
No, that would give you Py2+, which won't happen. To get pyridine from pyridinium N-oxide you need nucleophilic abstraction of O - i.e. the Py is the leaving group, not hydroxide/water.
I'd guess that SNAr reactions (for example with hydroxide: pyridine N-oxide
More
VOTE