Synthesis, crystal and molecular structures, and steroechemical nonrigidity ofN-(chlorodimethylgermylmethyl)-andN-(bromodimethylgermylmethyl)-N-[(S)-1-phenylethyl]acetamides andN-(chlorodimethylgermylmethyl)-4-phenyl-2-pyrrolidone |
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| Authors: | S Yu Bylikin S A Pogozhikh V N Khrustalev Vad V Negrebetsky A G Shipov Yu E Ovchinnikov and Yu I Baukov |
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| Institution: | (1) Russian State Medical University, 1 ul. Ostrovityanova, 117869 Moscow, Russian Federation;(2) V. I. Lenin Moscow State Pedagogical University, 1 ul. M. Pirogovskaya, 119891 Moscow, Russian Federation;(3) A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813 Moscow, Russian Federation |
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| Abstract: | RacemicN-(chlorodimethylgermylmethyl)-4-phenyl-2-pyrrolidone and the first optically active amide derivatives containing the asymmetrical
carbon atom and the five-coordinate germanium atom,viz.,N-(chlorodimethylgermylmethyl)- andN-(bromodimethylgermyl-methyl)-N-(S)-1-phenylethyl] acetamides, were synthesized. Their structures were established by X-ray diffraction analysis. The geometric
characteristics of the trigonal-bipyramidal valence environment about the germanium atoms are compared with those of analogous
enantiomeric silicon compounds and the related five-coordinate germanium compounds. The barriers to permutational isomerization
of the title compounds were determined by dynamic1H NMR spectroscopy. It was found that these barriers are higher than those of the corresponding silicon analogs.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 137–144, January, 2000. |
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| Keywords: | five-coordinate germanium compounds synthesis X-ray diffraction study stereochemical nonrigidity dynamic and multinuclear NMR spectroscopy optical activity |
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