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Updated: Jun 22, 2025

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
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Vibrational Features of Oxyamines: A Comparative Study of N,N-Diethylhydroxylamine and N,N-Diethylacetyloxyamine

Emanuele Pizzano1,2, Filippo Baroncelli1, Sonia Melandri1,3,4

  • 1Department of Chemistry G. Ciamician, University of Bologna, Bologna, Italy.

Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry
|July 4, 2024
PubMed

Keywords:
Conformational SpaceInfrared SpectroscopyNear-Infrared SpectroscopyOxyamineQuantum Mechanical ModelingSynthesis

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Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
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The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’...
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In proton NMR spectroscopy, primary amines and secondary amines showcase their N–H protons as a broad signal in the chemical shift range between δ 0.5 and 5 ppm. The exact position in this range depends on several factors, including sample concentration, hydrogen bonding, and the type of solvent used. Since amine protons undergo fast proton exchange in solution, the protons are labile and therefore do not participate in any splitting with adjacent protons. Thus, the observed peak is...
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