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- W2112423906 abstract "The Schiff base of all-trans-retinal was investigated in organic solution by 1H- and 13C-NMR. at high field. Complete assignment of the 1H-NMR. peaks of N-butyl-(all-trans-retinylidene)amine (2) and the N-butyl-(all-trans-retinylidene)-ammonium ion (3) was achieved by INDOR (internuclear double resonance). The vicinal proton coupling constants of the polyene chain show that the π-bond orders remain unchanged in N-butyl-(all-trans-retinylidene)amine relative to all-trans-retinal (1), but change towards larger π-delocalization in the N-butyl-(all-trans-retinylidene)ammonium ion. At −-61° only one isomer of N-butyl-(all-trans-retinylidene)ammonium was observed. This was shown to be trans at the imine linkage and independent of the solvent. The trifluoroacetic acid counter-ion can approach the positive charge of the N-atom in the weakly polar solvent dichloromethane but not in the leveling solvent methanol. In dichloromethane the nature of the 1:1 complex is a H-bonded (O−…H-N+) ion-pair whose rate of breaking and forming is rapid at RT. Strong stabilization of the ion-pair resulted from homo-conjugation with a second molecule of trifluoroacetic acid. Excess of acid efficiently diminished the isomerization rate at the C,N-bond." @default.
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- W2112423906 date "1981-11-04" @default.
- W2112423906 modified "2023-10-16" @default.
- W2112423906 title "A Study ofN-Butyl-(all-trans-retinylidene)amine and Its Protonated Species by1H- and13C-NMR. Spectroscopy" @default.
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- W2112423906 doi "https://doi.org/10.1002/hlca.19810640702" @default.
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