By Zvi Rappoport
Foreign individuals current papers fascinated by the structural, theoretical and artificial houses of enamines which act as vital intermediates in lots of syntheses of natural compounds containing oxygen. Cycloaddition reactions, electrochemistry, hydrolysis and biochemistry of enamines; enediamines; and metalated enamines are one of the subject matters mentioned.
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Ground state geometry. Vinylamine CHz=CHNHz (115) is the simplest prototype of aliphatic enamines and small enough to be studied by calculations of high precision. Of strong interest is the geometry of the amino group, which may be coplanar to the vinyl group (sp2-hybridized nitrogen) or adopt pyramidality (sp3-nitrogen) and may show additional rotational twist around the C-N bond. 2uo indicate non-planarity of the amino group. The six possible conformations 116121 are shown in Scheme 6. A complete geometry optimizationz0' for 115 using the semi-empirical approximate ab initio SCF MO method PRDDO (partial retention of diatomic differential overlapzoz) leads to the results presented in Figure 2.
E. 6-31G**//3-21G. + 3. Vinylamine a. Ground state geometry. Vinylamine CHz=CHNHz (115) is the simplest prototype of aliphatic enamines and small enough to be studied by calculations of high precision. Of strong interest is the geometry of the amino group, which may be coplanar to the vinyl group (sp2-hybridized nitrogen) or adopt pyramidality (sp3-nitrogen) and may show additional rotational twist around the C-N bond. 2uo indicate non-planarity of the amino group. The six possible conformations 116121 are shown in Scheme 6.
6-31G*lg4. e. 6-31G**194or 6-311G** 193,indicate the additional presence of polarization 2p orbitals on hydrogens. Especially for negatively charged systems, diffuse s- or p-type functions of high quantum numbers may be necessary. e. 3-21 + G or 6-31 G**. Optimizations of molecular geometries may be performed with a simpler basis set followed by a single-point Hartree-Fock (HF) calculation with a larger basis set for that derived geometry. e. 6-31G**//3-21G. + 3. Vinylamine a. Ground state geometry.