TY - JOUR A1 - Dushenko, G. A1 - Mikhailov, I. A1 - Reck, Günter A1 - Schulz, Burkhard A1 - Zschunke, Adolf A1 - Kharabaev, N. A1 - Minkin, V. T1 - Structure and Tautomerism of Cyclopentadiene Derivatives - IX. Synthesis and Structure of Substituted N-Cyclopentadienyl Amidinium Ylides N2 - A procedure has been developed for the synthesis of N-cyclopentadienyl amidinium ylides of the general formula C5(CO2Me)4[ArNC(Ar')NHAr]. According to the X-ray diffraction data, 1H and 13C NMR spectroscopy, and MNDO quantum-chemical calculations, the title compounds have a zwitterionic structure with the positive charge localized over the amidine NÄCÄN triad, and the negative charge, over the cyclopentadiene fragment. The configuration of the amidine moiety is stabilized by additional interaction of the NH hydrogen atom with the negatively charged cyclopentadiene ring (-bonding). The ylides are chiral due to atropoisomerism arising from a high energy barrier (G 298 >25 kcal/mol) to rotation of the Ar' substituent about the ordinary CÄC bond in the amidinium fragment. PY - 2002 DO - https://doi.org/10.1023/A:1020897411534 SN - 1070-4280 SN - 1608-3393 VL - 38 IS - 7 SP - 982 EP - 994 PB - MAIK Nauka/Interperiodica Publ. CY - Moscow AN - OPUS4-1556 LA - eng AD - Bundesanstalt fuer Materialforschung und -pruefung (BAM), Berlin, Germany ER -