Questions tagged [amines]

For questions about amines - organic compounds with a basic nitrogen with a lone pair, also occasionally referred to as derivatives of ammonia. Not to be confused with amides, for which the tag [carbonyl-compounds] is to be used.

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Can aniline be made with the method described in Dr Stone?

In Dr Stone, the main character makes aniline by rinsing coal tar with HCl, then mixing in ethyl acetate. See the image below. Is a method like this possible? What is occurring here?
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2k views

Reaction of amines with diethyl oxalate (Hofmann separation method)

Why does only one molecule of secondary amine react with diethyl oxalate and two molecules of primary amine react with diethyl oxalate? I feel secondary amine also should have reacted similar to ...
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How to theoretically predict thermodynamic stability?

Let's say we have $\ce{CH3-NH2}$ undergoing Hoffman's exhaustive methylation with $\ce{CH3-Cl}$. In which case side reactions such as $\ce{CH3-NH2 + CH3-NH2 -> CH3NHCH3 + NH3}$ would also occur. ...
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264 views

What is the average chain length of a glutaraldehyde crosslink between primary amines?

Imagine I'm performing a primary amine to primary amine (i.e. PA to PA) crosslinking reaction at $37~^{\circ}\mathrm{C}$ in phosphate-buffered saline (pH $\approx 7.4$) with glutaraldehyde drawn from ...
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243 views

Diazo Coupling reaction with para-substituted phenol?

Usually Diazo coupling occurs at para-position unless the para-position is occupied, in which case coupling occurs at ortho-position. While solving questions I found in both the cases as shown, the ...
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45 views

Relationship between structure and shock sensitivity for branched vs straight hydrocarbons and ammonium ions

In p. 137 of John D. Clark's Ignition! (in the new edition), Clark reports an interesting observation regarding the shock sensitivity of different isomers of alkyls and ammonium salts. Specifically, ...
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215 views

On what factors does amine inversion depend

What factors promote amine inversion? Like bulky groups around the nitrogen atom or less sterically crowding groups? Are there any other factors that affect amine inversion? Does the ...
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109 views

effect of different groups on Amine inversion

I know different groups attached to the nitrogen atom affect the amine inversion barrier, but is it due to steric factors or orbital interaction factors, eg. $\ce{(i-Pr)2NMe}$ vs $\ce{NCl3}$.
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269 views

Precise explanation of macrocyclic effect

In most of the books, the reason of macrocyclic effect is given that It occurs due to preorganised structure of macro-cyclic ligand.  But a proper explanation of these two particular examples isn't ...
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437 views

Selectivity of Zinin Reduction

What is it, that makes the Zinin Reduction a selective reduction, and not a complete reduction, in the case of dinitrobenzenes? Also, is the reaction a selective one even when it is done for aliphatic ...
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133 views

Do amino groups need to be protected during a Clemmensen reduction?

In class, we learned about the Clemmensen reduction of carbonyl groups to the corresponding hydrocarbon. This is all well and good, except that it would also seem that the conditions used in the ...
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1answer
478 views

Preparing an amine from an azide

Is there any mechanism available for reduction of alkyl azides to amines. One of the reactions is conversion by $\ce{Na}$ in ethanol or by $\ce{LiAlH4}$. But how do these proceed? $\ce{LiAlH4}$ will ...
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43 views

Reaction of diamines with carboxylic acids to form imidazole

I've recently came across this reaction and my guess is that firstly an amide forms that later reacts with the second amine group. Is this a general reaction? Does it matter if the compounds used are ...
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61 views

Basicity comparison between pyridine amines and other compounds

In cases 1, 2, 3, the compounds will resonate, thus giving them more stability. Firstly, I want to know whether nitrogen has a +M effect? (due to it having a lone pair of electrons?) In case 1, ...
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Can catecholamines be quantified by HPLC-MS/MS at high pH?

It seems that most HPLC-MS/MS methods used for quantitation of catecholamines (epinephrine, norepinephrine and dopamine, specifically) operate at low pH (commonly 3.0), and therefore demand the ...
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109 views

Electron donating ability of substituted amines on aromatic ring

How would you arrange the conjugate bases of the following amines in order of electron donating ability as EDGs as substituents on an aromatic ring? $\ce{NH3}$, $\ce{(C2H5)(C2H4CN)NH}$, $\ce{(C2H4OH)...
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381 views

How to explain the different regioselectivity of ketones/imines reacting with LDA?

When 1 equivalent of LDA is reacted with, for example, 2-pentanone, you get the thermodynamic (more substituted) product. But when you react butan-2-imine with 1.0 LDA, you receive the kinetic (less ...
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261 views

Primary amine versus phosphoramidate reactivity with succinate esters

I have posted two reactions below. The top reaction is well known and occurs readily and near quantitatively (e.g. in protein modification), while the bottom reaction to my knowledge does not exist in ...
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1answer
65 views

Confusion Regarding Nitrogen Inversion

In nitrogen inversion, the lone pair changes its direction continuously. Does this in any way delocalize the charge density on the nitrogen making it less nucleophilic and less basic than another ...
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122 views

Does aniline react with FeBr₃?

I have read that aniline does not undergo Friedel–Crafts reaction because it complexes with Lewis acid $\ce{AlCl3}.$ Will it also react with $\ce{FeBr3}$ during bromination (to receive a 3-bromo ...
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19 views

Alkylation before ring closure?

So, another question from my side. I have been thinking about the folowing reaction: The reaction above exists and was already done on two occasions and reportedly works really well and it seems to ...
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620 views

Why is C2H5 a stronger +I group than CH3?

While reading about the basic character of amines, I came across a note which said that $\ce{CH3-CH2-NH2}$ was more stable than $\ce{CH3-NH2}$ as $\ce{C2H5}$ was a stronger +I group than $\ce{CH3}$. ...
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174 views

Why ammonium salts can not undergo substitution

Why is ammonium salt, such as RNH3+, can not react with nucleophiles like HI to give RI and NH4+? The reaction is pretty much like the substitution of alcohol in acid condition. In my opinion, NH3 (...
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327 views

Why can tertiary amines not show chirality?

Why is a tertiary amine with three different substituents not chiral? Doesn't the lone pair represent a fourth, different substituent?
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3k views

Why is phenol more acidic than aniline?

I find that there are two contradicting factors at play here: 1) On removing proton, negative charge on oxygen is more stable than it is on nitrogen (because of greater electronegativity of oxygen). ...
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174 views

Why have citric acid only a denticity of 3 and tartaric acid of only 2?

Why can't the hydroxyl-groups in citric acid (denticity 3) or in tartaric acid (denticity 2) contribute to the denticity, as there are doing it in aminoethylethanolamine (denticity 3) Why do the ...
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74 views

Can amines in acidic medium last for long?

I have been thinking of a situation where amines are kept in moderately-to-highly acidic media. In such a case, the amines would assume the protonated forms: $$\ce{RNH2 + H3O+ <=>> RNH3+ + ...
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Direct conversion of amides to esters

Rarely does the literature describe the synthesis of esters from amides. I understand that amides are a relatively unreactive functional group but they can easily be hydrolysed to give carboxylic ...
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69 views

Infrared absorption spectrum of primary amides?

It's my understanding that the infrared absorption spectrum of primary amides beyond having a broad peak also has 2 sharp peaks representing the symmetric and antisymmetric stretch. My question is why ...
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1k views

What is the graphical formula when nitrobenzene is added to HCL and tin?

On the image i want to work out the structure of compound Q. I know that it is a reduction reaction. However why is it that the answer to this question is not C6H5NH2, but is actually (C6H5NH3)+Cl-
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393 views

pKa values and basicity

In considering basicity (particularly of amines), often I find included with the compound a pKa. I understand that the higher the pKa of the conjugate acid, the stronger the base. But when the pKa is ...
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385 views

Why do the amino groups in EDTA deprotonate first, in contrast to amino acids?

We know that in amino acids, carboxylic acid groups deprotonate first than the amine groups. For example, in alanine, $\mathrm{p}K_\mathrm{a,\ce{COOH}} = 2.34$, $\mathrm{p}K_\mathrm{a,\ce{NH3+}} = 9....
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Why does some coffee smell like urine?

I can smell a urine like odour from some coffees. I don't seem to be alone in this as there are multiple reports on the internet of people having the same experience. I have read from a few posts ...
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Order of nucleophilicity of Nitrogen atoms in adenine

I recently stumbled upon a question that got me thinking. It goes something like this: Find the major product of the following reaction: There were 3 options given: So it basically aims ...
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What is Liebermann nitroso test?

From the articles in the internet , I found that there are two reactions which are being called Lieberman nitroso test . One is the test of 2 degree amine in which a 2 degree amine is converted to N -...
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Why is the trimethylammonium group a stronger electron withdrawing group than the nitro group?

I was working on a question that basically boils down to deciding whether the nitro group ($\ce{-NO2}$) or the trimethylammonium group ($\ce{-N+(CH3)3}$) on a benzene ring, is a stronger electron ...
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Thermodynamic data related to diazotization reaction

Is there any thermodynamic data available for diazotization of aniline and also for the reduction of the diazonium salt using sodium sulfite? I also want to know the heat of reaction for both the ...
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139 views

Mechanism for formation of amides from ammonium carboxylate salts

One of the reactions that you can do with a carboxylic acid is to react it with ammonia or an amine, which produces the corresponding ammonium carboxylate salt. When this salt is heated, amide is ...