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  • organic chemistry - Why are amidines more basic than amines . . .
    Amidines can be thought of as carboxylic acid derivatives with the carbonyl oxygen replaced by a nitrogen and hydrogen atom; amidines exhibit conjugation Amidines are more basic (less acidic) than
  • organic chemistry - Amidine synthesis from nitrile and dimethylamine . . .
    Amidine synthesis from nitrile and dimethylamine using n-Buli as a base Ask Question Asked 2 years, 5 months ago Modified 2 years, 5 months ago
  • Why are amidines so much more basic than amides?
    Since we can draw more significant resonance structures for the amidine case, the protonated amidine is more stable than the protonated amide This difference in protonated product stabilities explains why amidines are more basic than amides
  • organic chemistry - Comparing the basicities of guanidine, acetamidine . . .
    The actual number of resonance structures is inconsequential: what matters is whether they are significant contributors to the resonance hybrid This issue has been discussed at length, particularly in the case of carboxylic acids vs phenols Along this line of thought, the resonance structures that involve cationic carbon with six valence electrons are not really worth considering Octet
  • Is nitrogen of aniline sp² or sp³ hybridized? [duplicate]
    The nitrogen in aniline is somewhere between $\mathrm {sp^3}$ and $\mathrm {sp^2}$ hybridized, probably closer to the $\mathrm {sp^2}$ side We are correctly taught that the nitrogen in simple aliphatic amines is pyramidal ($\mathrm {sp^3}$ hybridized) However in aniline, due to the resonance interaction between the aromatic ring and the nitrogen lone pair, considerable flattening of the
  • organic chemistry - Why is guanidine considered a strong base . . .
    Wikipedia notes that if a base (in water solution) has a conjugate acid whose $\mathrm {p}K_\mathrm {a}$ exceeds $13,$ it's a strong base The criterion is (apparently) based on complete or at least predominant dissociation up to $0 1$ molar Guanidine makes it, ergo a strong base
  • Attack of amine on amide - Chemistry Stack Exchange
    I am confused with the last step of clozapine synthesis: How can the amine group attack the amide group to form the amidine in such acidic environment? Is the intermolecular reaction between an ami
  • Comparing basicity of imidazole and 2-imidazoline
    imidazole: Already aromatic 2-imidazoline: Aliphatic amidine In the conjugate acid of imidazole there is considerable loss of aromatic character because now the pyrrole like Nitrogen atom also gets positive formal charge on it in some of the resonating structures Such N atom now hesitates more to delocalise its electrons over entire ring
  • On the stabler tautomer in amide-imidic acid tautomerism
    In the section on acid-catalysed hydrolysis of nitriles, this webpage has the following line of reasoning; the more stable amide tautomer predominates the (following) equilibrium (credit) How





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