# Tag Info

10

The heterocycle in this question is indole and is aromatic. This means that the N lone pair is delocalised and not readily available for nucleophilic attack. Think of it as similar in reactivity to a secondary amide nitrogen RCONHR. Generally you need to formally deprotonate to functionalise, though there are some interesting techniques using carbonyl azoles ...

7

Amide analogue of lactons are lactams, their tautomeric forms are lactims. Citing from the IUPAC Nomenclature of Organic Chemistry (Preferred names 2013): P-66.1.5.1 Lactams and lactims Intramolecular amides of amino carboxylic acids, $\ce{-CO-NH\bond{-}}$, are called ‘lactams’ and their tautomers, $\ce{-C(OH)=N\bond{-}}$, are ‘lactims’. Lactams ...

4

NO, this is not a viable way to make amides. Phthamide anion will react with acyl halides, but the problem arises with the second step, the removal of the phthalimido group. The usual conditions described here of hydrolysis with hydroxide or reaction with hydrazine will result in removal of the acyl group to reform phthalimide plus the carboxylic acid, in ...

3

You have a false dichotomy. Diamines and diacids can form salts with doubly charged anions and cations. Sadly, simply searching SigmaAldrich’s catalogue for the phrase diammonium did not turn up any example; however, I assume this is because these salts are unlikely to be used and thus wouldn’t sell. Chemically, proton transfer is one of the fastest ...

2

Not according to the commonly accepted mechanism here The first step is The nucleophilic H from the hydride reagent adds to the electrophilic C in the polar carbonyl group of the ester. Note: the pKa of primary amides is in the 22-25 range so not close to alcohols.

2

The answer, as with so much chemistry, is it depends. What substrate are you hydrolysing, is it a primary, secondary or tertiary amide? What else is in the molecule that you want to preserve? Both acid and base hydrolysis require concentrated conditions and elevated temperature. There is a lab procedure here that uses sodium hydroxide in water at reflux to ...

1

Yes, amide bonds can fragment during electrospray ionization. Intentional fragmentation in a collision cell Amide bonds are intentionally fragmented in mass spectrometers all the time, during proteomics analysis. In that case, peptides are ionized, particular ions are isolated (by the quadrupole of the mass spectrometer), and then the intact peptide ions ...

1

Cyclic amides are known as lactams. They can be a β-lactam which is a 4-membered ring, a γ-lactam which is a 5-membered ring, a δ-lactam which is a 6- membered ring, an ε-lactam which is 7-membered ring, and so on. An example of a drug containing a β-lactam ring is ezetimibe. Antibiotics that contain a β-lactam ring are collectively known as β-lactam ...

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