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N-Methylacetamide is a flammable, difficult to ignite, hygroscopic, crystalline, colourless solid with a faint odor that is soluble in water. [1] Several isomeric forms are known. [8] [9] In solution, it is 97–100% present as the Z isomer with a polymeric structure. [10] [4] The compound has a high dielectric constant of 191.3 at 32 °C. [11]
The related compound N,N-dimethylacetamide (DMA) is more widely used, but it is not prepared from acetamide. Acetamide can be considered an intermediate between acetone, which has two methyl (CH 3) groups either side of the carbonyl (CO), and urea which has two amide (NH 2) groups in those locations.
The chemical reactions of dimethylacetamide are typical of N,N-disubstituted amides. Hydrolysis of the acyl-N bond occurs in the presence of acids: CH 3 CON(CH 3) 2 + H 2 O + HCl → CH 3 COOH + (CH 3) 2 NH 2 + Cl −. However, it is resistant to bases. For this reason DMA is a useful solvent for reactions involving strong bases such as sodium ...
Bis(trimethylsilyl)acetamide (BSA) is an organosilicon compound with the formula MeC(OSiMe 3)NSiMe 3 (Me = CH 3). It is a colorless liquid that is soluble in diverse organic solvents, but reacts rapidly with moisture and solvents containing OH and NH groups .
Structure of acetamide hydrogen-bonded dimer from X-ray crystallography. Selected distances: C-O: 1.243, C-N, 1.325, N---O, 2.925 Å. Color code: red = O, blue = N, gray = C, white = H. [8] The lone pair of electrons on the nitrogen atom is delocalized into the Carbonyl group, thus forming a partial double bond between nitrogen and carbon.
N-Methyl-2-pyrrolidone (NMP) is an organic compound consisting of a 5-membered lactam. It is a colorless liquid, although impure samples can appear yellow. It is miscible with water and with most common organic solvents. It also belongs to the class of dipolar aprotic solvents such as dimethylformamide and dimethyl sulfoxide.
The vast majority of these procedures utilize the commercially available salt N,O-dimethylhydroxylamine hydrochloride [MeO(Me)NH•HCl], which is typically easier to handle than the free amine. [6] Treatment of an ester or lactone with AlMe 3 or AlMe 2 Cl affords the corresponding Weinreb amide in good yields. Alternatively, non-nucleophilic ...
Both are major contributors to the overall structure, so much so that the amide bond between the carbonyl carbon and the amide nitrogen has significant double bond character. The energy barrier for rotation about an amide bond is 75–85 kJ/mol (18–20 kcal/mol), much larger than values observed for normal single bonds.