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Gabriel synthesis part 2: removal of phthalimide
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Myron Dean
Gabriel synthesis part 2: removal of phthalimide
Phthalimide anion is more stable compared to benzamide anion because it has two carbonyls instead of one and thus, a more extended anionic amide conjugation. But phthalimide extended and stable conjugation can also be cationic (and it is) by the nitrogen electron pair, that helps the hydrazine attack to one carbonyl (amide structure remains) that finally forms phthalhydrazide (the conjugated form of the aromatic phthalazine-1,4-diol).
Phthalimide anion is more stable compared to benzamide anion because it has two carbonyls instead of one and thus, a more extended anionic amide conjugation. But phthalimide extended and stable conjugation can also be cationic (and it is) by the nitrogen electron pair, that helps the hydrazine attack to one carbonyl (amide structure remains) that finally forms phthalhydrazide (the conjugated form of the aromatic phthalazine-1,4-diol).
Phthalimide is acidic. When it loses a proton, the negative charge can delocalize to the carbonyl groups. So, phthalimide potassium salt is easier to prepare than benzamide potassium salt. Thanks for posing another question, but I don't see the link with the reactivity of hydrazine with the carbonyls (in either phthalimide or benzamide, being present in the same molecule)?
Phthalimide is acidic. When it loses a proton, the negative charge can delocalize to the carbonyl groups. So, phthalimide potassium salt is easier to prepare than benzamide potassium salt. Thanks for posing another question, but I don't see the link with the reactivity of hydrazine with the carbonyls (in either phthalimide or benzamide, being present in the same molecule)?
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Thanks for posing another question, but I don't see the link with the reactivity of hydrazine with the carbonyls (in either phthalimide or benzamide, being present in the same molecule)?
Thanks for posing another question, but I don't see the link with the reactivity of hydrazine with the carbonyls (in either phthalimide or benzamide, being present in the same molecule)?
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