565233-17-2Relevant academic research and scientific papers
Effect of through-bond interaction on conformation and structure in rod-shaped donor - acceptor systems: Part 2. Crystal structures of seven N-aryltropan-3-one (=8-aryl-8-azabicyclo[3.2.1]octan-3-one) derivatives
De Ridder, Dirk J. A.,Goubitz, Kees,Schenk, Henk,Krijnen, Bert,Verhoeven, Jan W.
, p. 812 - 826 (2003)
The crystal structures of seven N-aryltropan-3-one (=8-aryl-8-azabicyclo[3.2.1]octan-3-one) derivatives 1T1, 2T1, 2T2, 3T2, 5T2, 2T3, and 3T3 are presented (Fig. 2 and Tables 1-5) and discussed together with the derivatives 1T2 and 4T2 published previously. The piperidine ring adopts a chair conformation. In all structures, the aryl group is in the axial position, with the plane through the aryl C-atoms nearly perpendicular to the mirror plane of the piperidine ring. The through-bond interaction between the piperidine ring N-atom (one-electron donor) and the substituted exocyclic C=C bond (acceptor) not only elongates the central C-C bonds of the piperidine ring but also increases the pyrimidalization at C(4) of the piperidine ring. Flattening of the C(2)-C(6) part of the piperidine ring decreases the through-bond interaction.
