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organic chemistry - Why are amidines more basic than amines
WEBDec 27, 2018 · 6. 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 amines and amides by a factor of around 103 10 3 and 1012 10 12, respectively (from pKas).
Chemistry.stackexchange.comWhy are amidines so much more basic than amides?
WEBSince 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. edited. answered Jun 29, 2014 at 14:59. 85.2k 14 232 323.
Chemistry.stackexchange.comHydrolysis of an amidine derivative under acidic conditions
WEBJun 14, 2019 · The second example isn’t an imine to start with, it’s an amidine. Basically, in both cases the C=N bond is hydrolysed to C=O, but since the starting materials are different functional groups, the products are different too. $\endgroup$ –
Chemistry.stackexchange.comorganic chemistry - Amidine synthesis from nitrile and …
WEBOct 13, 2023 · I am making LiNMe2 using n-Buli (5.5 equiv.) and dimethylamine (5.0 equiv), -15 ºC, dry THF and under nitrogen atmosphere. I have been doing the reaction and I can observe conversion of starting ma
Chemistry.stackexchange.comorganic chemistry - Comparing basic strength order of amines
WEBDec 18, 2019 · 3. In the above question I was asked to compare the basic strength order. So I did it like this: The Nitrogen in I and II will not participate in resonance so the only effect it could produce is inductive (-I) . Now the compound IV has less resonating structures than the other compounds so the the Nitrogen atom will have larger electron density.
Chemistry.stackexchange.comorganic chemistry - Comparing the basicities of guanidine, …
WEBDec 12, 2015 · The following compounds were given, and I have to predict their order of basicity: Compound Name Chemical formula A Guanidine $\ce{(H2N)2C(NH)}$ B Acetamidine $\ce{(H3C)(H2N)C(NH)}$ C Benzamidi
Chemistry.stackexchange.comorganic chemistry - Why is guanidine considered a strong base
WEB1 Answer. Wikipedia notes that if a base (in water solution) has a conjugate acid whose pKa p K a exceeds 13, 13, it's a strong base. The criterion is (apparently) based on complete or at least predominant dissociation up to 0.1 0.1 molar. Guanidine makes it, ergo a …
Chemistry.stackexchange.comComparing basicity of imidazole and 2-imidazoline
WEBJun 23, 2017 · 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 …
Chemistry.stackexchange.comorganic chemistry - Why is DBU the most popular base with an …
WEBApr 9, 2016 · DBU is a popular amidine base because it can be deemed to be of lower nucleophilicity than cheaper amidines e.g. formamidine. It has been sometimes erroneously labelled as "non-nucleophilic" but seeing as it reacts with carbon dioxide and sulfonyl halides and anhydrides, this cannot be supported.
Chemistry.stackexchange.comOrtho-effect in substituted aromatic acids and bases
WEBJan 6, 2014 · When comparing o,m,p -toluidine basicities, the ortho effect is believed to explain why o -toluidine is weaker. But when comparing o,m,p -toluic acid basicities, the ortho effect is stated as a reason why o -toluic acid is stronger acid. I was told that the ortho effect is a phenomenon in which an ortho- group causes steric hindrance, forcing
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