Crystal structures of 8-arylethynyl substituted guanosine derivatives: are hydrogen-bonded ribbons a surprise?

Crystal structures of two 8-arylethynyl substituted guanosines reveal twisted hydrogen-bonded ribbon superstructures, contrasting a previous report of guanine quartet formation from 8-aryl derivatives. The structural switch is attributed to the stabilization of the ribbon through intermolecular [[sm...

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Bibliographic Details
Published in:CrystEngComm 2011-01, Vol.13 (17), p.5309-5312
Main Authors: Lim, Jaebum, Miljanić, Ognjen Š.
Format: Article
Language:English
Subjects:
Crystal structure
Derivatives
Guanines
Guanosines
Optimization
Ribbons
Stacking
Superstructures
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Summary:Crystal structures of two 8-arylethynyl substituted guanosines reveal twisted hydrogen-bonded ribbon superstructures, contrasting a previous report of guanine quartet formation from 8-aryl derivatives. The structural switch is attributed to the stabilization of the ribbon through intermolecular [[small pi][small pi]] stacking between the optimally positioned electron-poor arylethynyl substituents and electron-rich guanine nuclei.
ISSN:1466-8033
1466-8033
DOI:10.1039/c1ce05618b