NMR and X-ray analyses of triethyl 3,7,11-triphenylcyclonona[1,2- b;4,5- b′;7,8- b″]tripyrrole-2,6,10-tricarboxylate: reinvestigation of crown vs saddle conformation of cyclononatripyrroles

From X-ray analyses of 3,7,11-triphenylcyclonona[1,2- b;4,5- b′;7,8- b″]tripyrrole-2,6,10-tricarboxylate (CNTP 1 ), the molecules existed as saddle forms in both crystals of 1 ·3ClPh and 1 ·1/2CHCl 3. In the former crystal, hydrogen bonds between pyrrolic hydrogen and ester carbonyl oxygen spread tw...

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Bibliographic Details
Published in:Tetrahedron 2003, Vol.59 (5), p.601-605
Main Authors: Uno, Hidemitsu, Fumoto, Yumiko, Inoue, Kentarou, Ono, Noboru
Format: Article
Language:English
Subjects:
crown conformation
cyclononatripyrroles
hydrogen bonding
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Summary:From X-ray analyses of 3,7,11-triphenylcyclonona[1,2- b;4,5- b′;7,8- b″]tripyrrole-2,6,10-tricarboxylate (CNTP 1 ), the molecules existed as saddle forms in both crystals of 1 ·3ClPh and 1 ·1/2CHCl 3. In the former crystal, hydrogen bonds between pyrrolic hydrogen and ester carbonyl oxygen spread two-dimensionally, forming molecular sheets, between which the solvent molecules were included, while two independent molecules were bounded three-dimensionally by the hydrogen bonds in the latter. In CDCl 3, CNTP was observed to adopt a crown form, while interconversion of the conformers was observed in C 5D 5N. CNTP ( 1 ) existed as a crown form in CDCl 3 or showed rapid interconversion in C 6D 5N, while the saddle conformation was observed in crystalline states.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(02)01589-2