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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.

12
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2answers
390 views

Does aniline react with diazonium ions at C or N?

In the azo coupling of aniline with benzenediazonium cation, I thought of two possible products 1 and 2 that could be formed. However, I can't work out which will be preferred. What would be the major ...
1
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0answers
32 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 $\ce{CH3}$. ...
4
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1answer
79 views

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 ...
-1
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2answers
87 views

The nomenclature behind “Diacetonamine”

Please explain how the name “Diacetonamine” can be found by looking at the formula: $$\ce{(CH3)2C(NH2)CH2C(O)CH3}$$ Why is it called “Diaceto” if there only one $\ce{-C(O)CH3}$ group?
1
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1answer
91 views

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 ...
-1
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2answers
44 views

Feasibility of Electrophilic attack on the Nitrogen over the Phenyl ring of Aniline

I have learnt that the '-NH2' substituent attached to the phenyl ring, owing to the substitutent's highly positive mesomeric effect, activates the phenyl ring quite a lot for Electrophilic Aromatic ...
0
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0answers
31 views

Why don't zwitter ions show ortho effect?

I recently came across a statement which said that zwitter ions are an exception to the ortho effect. Is it because the ions attract each other and the -COOH group is brought back into the plane ...
0
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0answers
65 views

Arranging these aromatic amines according to their basic character

The problem asks to arrange theses amines in an increasing order of their basic character. Clearly 2 is less basic than 1, because $NO_2$ is a strong $e^-$ withdrawing group and it is going to show ...
0
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1answer
54 views

NMR of phenylethane amine

I did an undergraduate experiment and could use some help in interpreting the $\ce{^1H}$ NMR spectra. This was the task: About $\pu{5-10mg}$ (1-2 drops) distilled amine is weighed in a NMR tube. Put ...
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0answers
24 views

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 ...
3
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1answer
114 views

Can enamines be formed from α,β-unsaturated ketones?

This question was a result of discussion form here: α,β-unsaturated carbonyl compounds and alkyl addition The reaction below (condensation of cyclohexenone with a secondary amine) does not yield any ...
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0answers
46 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 (...
3
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0answers
64 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 ...
1
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0answers
163 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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1answer
45 views

Polyamides Reaction mechanism

I already know that polyamides are made through condensation polymerisation with a carboxylic acid and an amine. But how exactly does the mechanism work? If the reaction takes place in acid for ...
1
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1answer
61 views

How would 2-(chloromethyl)-1-methylpyrrolidine recyclize into 3-chloro-1-methylpiperidine with only water?

My Attempt I always get thrown off by mechanisms with just water as a solvent. I've attached my work as far as I could get but I'm not sure where to go from there. Thank you!
2
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2answers
105 views

Out of the given reagents, find the ones to be used to convert benzene to p-aminophenol

$\ce{Br2/FeBr3}$ $\ce{CH3Cl/AlCl3}$ $\ce{KMnO4}$ $\ce{HNO3/H2SO4}$ $\ce{NBS}$/hv $\ce{NaOH}$ $\ce{Sn/HCl}$ $\ce{NH4SH}$ $\ce{NaBH4}$ I'm able to get the amino group onto the ring by using 4 and 7. ...
0
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1answer
35 views

Solvents for monoalkylations?

Just beginning to grasp this. Betaphenylethylamine to n-methyl-b-pea. Can I use water instead of DMSOesque solvent in regards to cesium carbonate/hydroxide monohydrate? Also are molecular sieves ...
0
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1answer
980 views

Reaction of primary nitroalkane with nitrous acid

I was reading the reaction of primary nitroalkane with nitrous acid. I read this reaction Another mechanism which I saw: I am now confused whether the first mechanism occur or the second one.I ...
1
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1answer
303 views

What happens to a quaternary ammonium cation at a pH above its pKa?

I am working with a lipid and I have firm reasons to believe that its pKa is around 8. This lipid is a cationic lipid where the nitrogen is a quaternary amine with two lipid chains and two methyl ...
1
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1answer
209 views

Strong activation of phenoxide ion compared to others

I was told that that in phenoxide ion, benzene ring is very strongly activated. The order my teacher told me was phenol < amine < 2 degree amine < 3 degree amine < phenoxide (for ...
6
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2answers
230 views

What are the IUPAC names for singly- and doubly-protonated piperazine?

If ammonia, $\ce{NH3}$, is protonated, it becomes ammonium: $\ce{NH4+}$. If piperidine is protonated, it becomes piperidinium: If piperazine is protonated once, what does it become? By analogy, I ...
4
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2answers
71 views

Do alkyl halides with an alpha nitrogen atom undergo SN1 reaction?

Today, in my organic chemistry class, I learnt about the nucleophilic substitution reaction. The notes have stated that: Alkyl halides with $\alpha$ oxygen atom can also undergo SN1 reaction ...
2
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1answer
1k views

Which one is more basic: acetamide or aniline? [duplicate]

Which one is more basic: acetamide or aniline? I had approached the question by protonating both of the compounds. Then I judged them on the basis of the stability of the corresponding conjugate acid....
1
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2answers
205 views

Acid in Imine Formation

Why is a strong acid like $\ce{H2SO4}$ used for imine formation here instead of a weaker acid like TsOH? I thought that if the pH was too low, the amine molecule would get protonated to an ammonium, ...
1
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1answer
525 views

Comparison of basic strength of benzylamine and ammonia

According to me, ammonia should be the stronger base for two reasons: $\ce{-C_6H_5}$ group shows $-I$ effect, due to which electron density on $\ce{N}$ atom of benzylamine decreases steric hindrance ...
10
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1answer
152 views

What is the preferred IUPAC name of hexamethyldisilazane?

Hexamethyldisilazane (HMDS, $\ce{(SiMe3)2NH}$) and its conjugate base hexamethyldisilazide (as the Li/Na/K salt) find wide use in organic chemistry. In my quest to only use preferred IUPAC names in ...
3
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1answer
2k views

Product of primary amine and acid anhydride

How does an acid anhydride react with a primary amine? I thought it'll be some sort of condensation reaction, so I made the product by removing a water molecule and got a cyclic product. However, the ...
5
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2answers
3k views

Is steric inhibition of resonance or steric inhibition of protonation dominant in o-toluidine?

I wish to know which effect out of steric inhibition of resonance (SIR) or steric inhibition of protonation (SIP) is dominant over the other when comparing basicities of o-toluidine and aniline: ...
1
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0answers
290 views

Why is ethanol used in catalytic reduction of nitro group to an amine? [closed]

$$\ce{R-NO2 +C2H5OH + H2 (g)->[Pt/Pd/Ni] R-NH_2}$$ The above equation represents catalytic reduction of nitro group to amine. What is the role of ethanol in it? I understand that $\ce{Pt/Pd/Ni}$ ...
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0answers
1k 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). ...
1
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1answer
205 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....
4
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1answer
268 views

Can aniline autodeprotonate?

I had an argument with an assistant in my lab, as he stated that in a hypothetical reaction two aniline molecules could react in a way, that one takes a proton off of the other one, thus creating a $\...
3
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0answers
68 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)...
1
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1answer
3k views

Hoffman's Isocyanide test: How does addition of concentrated HCl degrade the isocyanide formed?

This question is regarding a laboratory procedure followed for Hoffman's Isocyanide test (also known as the "Carbylamine test") I've been taught that the isocyanide formed in this reaction is highly ...
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2answers
2k views

Does the amine group participate in resonance in aniline? [duplicate]

When we draw resonance structures of aniline, 8 electrons participate in resonance, making it antiaromatic. But in our school textbook, it is said to be aromatic. Does the lone pair of $\ce{NH2}$ ...
3
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0answers
60 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 $\ce{NCl3}$.
5
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1answer
97 views

Amine Inversion and Paramagnetism

In amine inversion, there is a planar $sp^2$ intermediate. The electron pair transferred from the blue lobe to the red one during the inversion. It is natural to assume, for a layman like me, that ...
-1
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1answer
346 views

Safest Methylating Agent

I am planning on doing some synthesis in the near future and due to safety purposes I am looking for a methylating agent that is both effective and safe. The substrate is a deprotonated amine and the ...
4
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1answer
651 views

Byproducts of LiAlH4 reduction of amides

I know that $\ce{LiAlH4}$ is able to reduce amides into amines, e.g. benzamide into benzylamine. However, I am unsure what other by-products are formed as a result. $$\ce{LiAlH4 + C6H5CONH2 -> ...
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0answers
234 views

How to find out which organic molecules would be good electron acceptors/donors on a GaAs semiconductor surface [closed]

I'm a physicist in way over my head. I have a list of organic molecules to investigate, all common aldehydes and amines. My supervisor wishes to know which of these molecules would be good electron ...
5
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2answers
350 views

Reduction of 1,4-benzoquinone in the synthesis of 1,5-diazocane

Synthesize 1,5-diazocane using only benzene as a source of carbon atoms, and ammonia as the only source of nitrogen atoms. My attempt: Noticing that the target compound has split the benzene ring, ...
1
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1answer
112 views

Organic nomenclature of substituted diamines

Nomenclature of substituted amines is done with the N-locants, with the N being used to indicate that a group is connected to the methyl group. I was wondering, therefore, on how to properly name a ...
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0answers
93 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 ...
4
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1answer
563 views

pKa of imidazoles

I was looking for the $\mathrm{p}K_\mathrm{a}$ of imidazole and found this $\mathrm{p}K_\mathrm{a}$ table [1]: \begin{array}{ll} \text{Compound} &\mathrm{p}K_\mathrm{a} \\ \hline \text{...
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0answers
80 views

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. ...
2
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1answer
298 views

Aromatic and aliphatic amines

Is benzylamine $\ce{C6H5CH2NH2}$ an aromatic or aliphatic amine? I've tried searching for it however different sources have conflicting information.
3
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1answer
489 views

Mechanism of Hofmann Rearrangement Reaction

In the Hofmann Rearrangement Reaction (in basic medium), when $\ce{RNH-}$ ion is produced, why does it not attack $\ce{Br2}$ or take $\ce{H+}$from the amide itself? Also, why does it take $\ce{H+}$ ...
0
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1answer
67 views

Which group is more suitable for metal nanoparticles functionalization? [closed]

I have synthesized bimetallic nanoparticles (gold core with a silver shell). I have two choices for functionalizing them, through thiol group or amine group. Which of them is more attracted to this ...
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0answers
63 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+ + ...