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Non‐Ionic Template Synthesis of Amide‐Linked Rotaxanes: Olefinic and Aliphatic Axle Building Blocks
Author(s) -
Jäger Ralf,
Baumann Sven,
Fischer Marco,
Safarowsky Oliver,
Nieger Martin,
Vögtle Fritz
Publication year - 1997
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719971114
Subject(s) - rotaxane , chemistry , amide , ionic bonding , hydrogen bond , molecule , polymer chemistry , axle , stereochemistry , combinatorial chemistry , organic chemistry , supramolecular chemistry , ion , mechanical engineering , engineering
The first synthesis of amide‐linked rotaxanes with non‐arene axle building blocks is reported. The threading synthesis of rotaxane 8 with olefinic fumaryl chloride proves that arene moieties are not necessary for non‐ionic template syntheses. Mass spectroscopic evidence of a rotaxane bearing an aliphatic axle, derived from succinic acid, revealed that hydrogen bonding, rather than π,π interactions, is the predominant template binding force. 1 H‐NMR titration studies on the threading synthesis of these mechanically bonded molecules were carried out. The association constants measured suggest that the incorporation of the corresponding monoamide monochloride (cf. 7 ), rather than the incorporation of the diacid dichloride (cf. 5 ), plays the key role in these rotaxane syntheses. The X‐ray structural analysis of a semi axle ( 14 ) reveals hydrogen bonding patterns characteristic of diamides.