Conformations of unsymmetrical N-t-butyl-N-substituted 2-phenylacetamides
| Autor: | A.D. Nikolić, Dušan Ž. Mijin, Dusan G. Antonovic, N.D. Stojanović, Slobodan D. Petrović |
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| Rok vydání: | 1997 |
| Předmět: |
010405 organic chemistry
Chemistry Stereochemistry N-t-butyl-N-substituted 2-phenylacetamides Organic Chemistry Substituent H-1 NMR Carbon-13 NMR 010402 general chemistry conformational isomers 01 natural sciences 0104 chemical sciences Analytical Chemistry Ion Inorganic Chemistry 2-Phenylacetamides chemistry.chemical_compound Fragmentation (mass spectrometry) Proton NMR C-13 NMR Conformational isomerism Spectroscopy Cis–trans isomerism |
| Zdroj: | Journal of Molecular Structure |
| ISSN: | 0022-2860 |
| DOI: | 10.1016/s0022-2860(96)09745-1 |
| Popis: | Various N - t -butyl- N -substituted 2-phenylacetamides, PhCH 2 CON( t -Bu)R, wherein R is methyl, ethyl, n -propyl, n -butyl, i -propyl, phenyl and cyclohexyl, were synthesized. Depending on the kind of substituent on the nitrogen atom, some of the examined amides exist in different conformational forms. 1 H NMR and 13 C NMR spectra of these unsymmetrically N , N -disubstituted amides have been studied and peaks have been assigned in each case to the two possible conformational isomers, arising from the lack of free rotation about the C(O)N bond. The relative distribution of cis and trans isomers has been established by means of different coupling constants and the NOE difference technique. Information about fragmentation routes, and the effect of overall and partial structures were obtained by the study of the metastable ions. The results are in accordance with our previous investigations of the structures of N , N -disubstituted 2-phenylacetamides. |
| Databáze: | OpenAIRE |
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