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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.

1 vote
0 answers
82 views

Why is quinuclidine more basic than triethylamine? [duplicate]

I am trying to compare the basic strength of two similar amines Usually this is done by comparing the relative stability of the ion formed on the protonation of nitrogen's lone pair. This can be done ...
mark's user avatar
  • 201
1 vote
0 answers
158 views

Aminium/Ammonium?

Chemdraw names this as 2-carboxyethan-1-aminium. Shouldn't it be ammonium? What's an aminium ion?
Arbish Ali's user avatar
3 votes
0 answers
101 views

Gabriel Phthalamide Synthesis of 1-Phenylethylamine

I had learnt that due to the nature of the Gabriel synthesis reaction being $S_{N}2$, the alkyl halide used must have a primary alkyl group. However, in an exam (JEE Main 2023), it was mentioned that ...
Srish Dutta's user avatar
1 vote
0 answers
63 views

Amidine synthesis from nitrile and dimethylamine using n-Buli as a base

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 ...
Bree's user avatar
  • 11
-4 votes
1 answer
74 views

Does ammonia gas neutralise Hcl salt of amines in dry non polar medium [closed]

I am trying to basify/neutralise the $\ce{HCl}$ salt of amine and other organic compounds by bubbling dry(or semi dry) ammonia gas through a column of the salt suspended in a non polar solvent like ...
The Entity's user avatar
-2 votes
1 answer
154 views

Is it possible to have multiple nitrogen atoms bonded to one carbon atom?

So I was wondering, if we replaced two of the hydrogens in methane with amine groups, would it be a stable compound? What about for R groups of varying size? Similarly, if I tried to make a compound ...
InactionBreedsMediocrity's user avatar
0 votes
0 answers
68 views

Discrepancies in basic strength of different amines

The order of basic strength of ethyl substituted amines is $\ce{(C2H5)2NH}$ > $\ce{(C2H5)3N}$ > $\ce{(C2H5)NH2}$ > $\ce{NH3}$ Which means secondary amine is more basic than tertiary followed ...
Harjot Dhillon's user avatar
4 votes
1 answer
337 views

What are the best conditions for coupling small molecules with EDC?

I want to couple a DNA oligo containing an amino group with another small molecule possessing a carboxyl group. I found protocols for EDC (1-ethyl-3-(3-dimethylaminopropyl)carbodiimide) coupling of ...
Brenlla's user avatar
  • 201
7 votes
1 answer
389 views

Lewis Structure of the Guanidinium Ion

In a problem, I was asked to find the Lewis structure of the guanidinium ion $\ce{C(NH2)3}^{+1}$. I followed the following steps which led me to an incorrect structure and I was hoping someone could ...
Johnny Smith's user avatar
-3 votes
1 answer
76 views

Decomposition of aliphatic diazo compounds [closed]

The oxidation of hydrazones produce a diazo compound: orgsyn.org - DIAZOPROPANE. An intermediate in the Bamford-Stevens reaction is a diazo moiety. When 2-diazopropane decomposes, does it produce 1-...
Jack's user avatar
  • 1
-4 votes
1 answer
135 views

What's the priority order of primary, secondary and tertiary amino groups in IUPAC nomenclature [closed]

It's a really simple question but I didn't get answer to this anywhere. What's the priority order of primary, secondary and tertiary amino groups in IUPAC nomenclature. For example what would be the ...
Valoruz's user avatar
  • 89
3 votes
0 answers
69 views

Difference of reactivity between anilines and alkyl amines

Imine synthesis is somewhat common and straightforward, to achieve good yields a good practice is to remove the water formed from the condensation reaction by means of a desiccating agent or a Dean-...
Mictlantecuhtli's user avatar
3 votes
1 answer
54 views

Will ethyl 2-amino-1H-imidazole-5-carboxylate undergo ester aminlysos with the primary amines of bPEI efficiently in methanol?

I was about to set up the following reaction, but before I do, I wanted to see if anyone has some suggestions or thinks this will not work: 24mmol Nboc protected ethyl 2-amino-1H-imidazole-5-...
toodles's user avatar
  • 137
4 votes
2 answers
421 views

Why does "bis-tris propane" have two pKa values?

Wikipedia gives two pKa values for "Bis-tris propane". What about bis-tris-propane gives this compound two pKa values where other compounds have only one? How am I to choose which pKa value ...
Nicholas DeMarco's user avatar
6 votes
0 answers
100 views

Why sulfur dissolved in ethylenediamine turns green?

Davis, R. E., & Nakshbendi, H. F. (1962). Sulfur in Amine Solvents. Journal of the American Chemical Society, 84(11), 2085–2090. doi:10.1021/ja00870a017 I've also done this experiment. But what ...
seilgu's user avatar
  • 281

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