The Molecular Structure of N-Methylacetamide

Mizushima, Shôji; Simanouti, Takehiko; Nagakura, Saburo; Kuratani, Kenji; Tsuboi, Masamichi; Baba, Hiroaki; Fujioka, Osamu

doi:10.1021/ja01164a048

Cited by 161 publications

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“…3,i) is completely analogous to the ester group. The anticonformation is strongly favored [50,511, and again only in formamides is there evidencer51l for another less stable isomer, supposed to be planar cis. The torsional barriers are not known, but they seem to be low in the single bonds on both sides.…”

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confidence: 98%

Conformational Aspects of Many‐Membered Rings

Dale

1966

Angew. Chem. Int. Ed. Engl.

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obtained in anhydrous dimethylformamide at 150 'C (Scheme 2,d). e) R e a c t i o n with AminesPoly-y-hydroxycrotonolactone reacts with amines in aqueous media at 20 to 50°C to give the ammonium salt of the polymeric y-hydroxy acid (see Scheme 2,el). In organic solvents, e.g. in an excess of the amine, higher reaction temperatures are required, and the polymeric y-hydroxy carboxamide is then formed (Scheme 2,ez). f) R e d u c t i o n with L i t h i u m T e t r a h y d r i d o a l u m i n a t e Polymeric crotonolactone can be smoothly reduced with LiAIH4 in tetrahydrofuran to give a water-soluble polymer of 2-butene-l,4-diol (Scheme 2,f). We are grateful to Professor Korte for his interest in this work. The stereochemistry of the various chemical groupings which constitute the structural units of ring systems isfirst reviewed. It is then shown that the strain-free possibilities even of large rings are restricted, and that the ring conformations theoretically derived generally correspond to those found by physical methods. Variations of physical properties and of cyclization yield in homologous series are explained on a conformational basis.[5] J. B. Hendrickson, J. Amer. chem. SOC. 83, 4537 (1961). [6] Earlier summaries: J. D. Dunirz and V. Prelog, Angew. Chem. 72, 896 (1960).

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confidence: 98%

Conformational Aspects of Many‐Membered Rings

Dale

1966

Angew. Chem. Int. Ed. Engl.

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“…The planar trans structure of n-methyl acetamide has been proved by Raman, infrared, ultraviolet, and dipole measurements (109). The same structure of the peptide bond has been shown by x-ray crystallographic studies for glycylglycine, acetyl glycine, etc.…”

Section: Bond Lengthmentioning

confidence: 67%

Experimental Molecular Structure

Mizushima¹,

Shimanouchi²

1956

Annu. Rev. Phys. Chem.

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“…In order to ascertain if there are bands due to [4] vIo2 = 2 0 , + 6X, , + X I , + X13 simultaneous excitation in the overtone region similar to those which were found for alcohols [5] vzo2 = 202 + 6x22 + X12 + X23 (15) we carried out an isotopic isolation experiment measuring the spectrum of a 1 :9 mixture of NMA and NMA-N-d from 22 to -190 "C. No significant changes were observed. This eliminates this possibility which was unlikely anyway, since no two N-H bonds are directly linked together in the amide polymers or oligomers.…”

Section: Overtones and Combination Tonesmentioning

confidence: 99%

A Low Temperature Infrared Study of Hydrogen Bonding in N-Alkylacetamides

Bernard‐Houplain¹,

Sándorfy²

1973

Can. J. Chem.

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The infrared spectra of N-niethylacetamide and two other secondary amides were measured in solution a t temperatures ranging from 22 to -190 'C in both the fundamental and the overtone regions. A t least two hydrogen bonded species are found as association increases with decreasing temperature. The effect of hydrogen bond formation on the anharnionicity of the NH stretching vibration and o n the NH stretching -N H bending coupling constant is examined.Les spectres infrarouges du N-methylacetamide et d e deux autres arnides secondaires ont kt6 mesurks en solution, a des temperatures allant de 22 a -190 "C, a la fois dans la region de la fondamentale et dans celle des harmoniques. O n a Ctabli I'existence d'au moins deux especes associees par liaison hydrogene en abaissant la temperature. On a examine I'effet de la liaison hydrogene sur I'anharmonicitk d e la vibration de valence N H , et sur la constante d e couplage entre les vibrations N H d e valence et de deforniation.

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The Molecular Structure of N-Methylacetamide

Cited by 161 publications

References 0 publications

Conformational Aspects of Many‐Membered Rings

Conformational Aspects of Many‐Membered Rings

Experimental Molecular Structure

A Low Temperature Infrared Study of Hydrogen Bonding in N-Alkylacetamides

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