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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

✍ Scribed by Dirk J. A. De Ridder; Kees Goubitz; Henk Schenk; Bert Krijnen; Jan W. Verhoeven

Publisher
John Wiley and Sons
Year
2003
Tongue
German
Weight
206 KB
Volume
86
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

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.

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Effect of Through-Bond Interaction on Conformation and Structure in Rod-Shaped Donor–Acceptor Systems. Part 1 : Crystal Structures of Five N-Arylpiperidin-4-one Derivatives
✍ Dirk J. A. De Ridder; Kees Goubitz; Henk Schenk; Bert Krijnen; Jan W. Verhoeven 📂 Article 📅 2003 🏛 John Wiley and Sons 🌐 German ⚖ 142 KB

## Abstract The crystal structures of five __N__‐arylpiperidin‐4‐one derivatives **2P2, 3P2, 5P2, 1P3**, and **2P3** are presented (__Fig. 2__ and __Tables 1–5__) and discussed together with the derivatives **1P2** and **4P2** published previously. In all but one structure, **1P2**, the aryl group