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Beilstein J. Org. Chem. 2018, 14, 2940–2948, doi:10.3762/bjoc.14.273
Graphical Abstract
Scheme 1: Protonation of DMAN.
Scheme 2: Protonation equilibria for 2 and 3.
Scheme 3: Protonation of imine 4a with perchloric acid.
Scheme 4: Synthesis of investigated substrates (yields obtained by paths a and b are denoted by a correspondi...
Scheme 5: Preparation of protonated forms of imines 4–7.
Figure 1: C=NH Signal regions of temperature-depending 1H NMR spectra for compounds 4a–7a, acetone-d6.
Scheme 6: E/Z-Isomerisation of ketimines 4a–7a.
Figure 2: Molecular structure of imines 6a (a) and 4a (b). The H···O distance for 6a is shown.
Figure 3: Optimised geometry and energy difference ΔE = EE – EZ (kcal/mol) for imines 4a–7a (B3LYP/6-311+G(d,...
Figure 4: 1H NMR spectra of imines 4b–7b (4b’–7b’) in DMSO-d6, 25 °C (the signals of the forms protonated at ...
Scheme 7: Switching of protonation sites in imines 4b–7b.
Figure 5: Optimised geometries and energy differences ΔE = Eb’ – Eb (kcal/mol) for different sites of protona...
Figure 6: Molecular structure of protonated imines 4a·HClO4 (a) and 6b·EtOH (b).
Scheme 8: Protonation of the out-inverted dialkylamino group.
Scheme 9: Examples of proton sponges with stabilised in,out-conformation.
Figure 7: C=NH2+ Signal regions of temperature-depending spectra for compounds 4c–7c, acetone-d6.
Figure 8: Molecular structure of dication 6с.