Optische Aktivität und zwischenmolekulare Kräfte, III. Physikalische Eigenschaften einiger <i>p.p</i>′‐disubstituierter <i>N</i>‐Benzoyl‐α‐phenyl‐äthylamine

Nerdel, Friedrich; Goetz, Horst; Fenske, M.

doi:10.1002/jlac.19636650104

Cited by 4 publications

(5 citation statements)

References 20 publications

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“…N -Methylacetamide ( 1 ) and N -ethylacetamide ( 2 ) were commercially available and used without further purification. Amides 3 , 4 , 5 , 6 , and 7 − 11 45 were prepared according to procedures described in the literature. NMR spectra for the latter substances having concentrations in the range of 5−12 mg/0.5 mL of CDCl 3 were recorded at 20 °C using either a 200 or 400 MHz spectrometer.…”

Section: Methodsmentioning

confidence: 99%

Can We Predict the Conformational Preference of Amides?

et al. 2001

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To what extent, if any, is the conformation of secondary amides revealed by theory? This question has now been addressed by computational methods using calculations at the B3LYP/6-31G level of theory and (1)H NMR spectroscopy. Both gas-phase and solvent studies predict a Z-anti conformation to be the lowest in energy for an evaluated series of acetamides. Moreover, Z-anti conformations may also be inferred from the chemical shifts of the N-CH alpha protons determined by NMR spectroscopy. Thus, a proton situated anti to the N-H proton consistently appears approximately 0.8 ppm further downfield than a proton situated gauche to the N-H proton. This finding, which could only be derived by using the DFT calculations of conformational preference as a guide to interpret the NMR data, might prove to be useful as a simple and convenient methodology for establishing amide conformation experimentally.

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Section: Methodsmentioning

confidence: 99%

Can We Predict the Conformational Preference of Amides?

et al. 2001

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“…It may be mentioned parenthetically that having determined the absolute rotation of the @)-(+)-ketone (34a) ([aID2' The enantiomeric excess of the intermediates (38a) and (39a) was established by comparison of the observed specific rotations with reported absolute values. 37 It is assumed that no racemisation takes place during the interconversion (39a) -(40a) + (41a) and that the product (41a) is the optically pure (R)-amine (41a). The (R,S)-amine (41) was prepared by a similar route from (R,S)-I -phenylethylamine.…”

Section: -58°34nmentioning

confidence: 99%

Base catalysed rearrangements involving ylide intermediates. Part 15. The mechanism of the Stevens [1,2] rearrangement

Ollis¹,

Rey²,

Sutherland³

1983

J. Chem. Soc., Perkin Trans. 1

105

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“…The CC14 solution was dried overnight with MgS04 and filtered, and the solvent was removed by distillation. The monobromo compound crystallized, (8) Wiselogle, F. Y.; Sonnenborn, H. Org. Synth.…”

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confidence: 99%