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Effect of Through‐Bond Interaction on Conformation and Structure in Rod‐Shaped Donor–Acceptor Systems. Part 1
Author(s) -
De Ridder Dirk J. A.,
Goubitz Kees,
Schenk Henk,
Krijnen Bert,
Verhoeven Jan W.
Publication year - 2003
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200390081
Subject(s) - chemistry , piperidine , ring (chemistry) , crystallography , acceptor , atom (system on chip) , cyclohexane conformation , aryl , crystal structure , stereochemistry , eclipsed conformation , group (periodic table) , hydrogen bond , molecule , organic chemistry , physics , alkyl , computer science , embedded system , condensed matter physics
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 is in an equatorial position. The piperidine ring adopts a normal chair conformation. In 1P2 , the piperidine ring central CC bonds are significantly elongated, which is consistent with the idea that through‐bond interaction is more pronounced in the axial conformation. Through‐bond interaction also influences the pyramidalization at the piperidine C(4)‐atom in such a way that a strong interaction is directing the ethylene C‐atom C(9) into the axial direction.