Title
Competition between methoxy-based and pyrazine-based synthons in methoxy-substituted distyrylpyrazines Competition between methoxy-based and pyrazine-based synthons in methoxy-substituted distyrylpyrazines
Author
Faculty/Department
Faculty of Sciences. Chemistry
Publication type
article
Publication
Subject
Chemistry
Source (journal)
Crystal growth & design
Volume/pages
11(2011) :4 , p. 1299-1309
ISSN
1528-7483
ISI
000289050100060
Carrier
E
Target language
English (eng)
Full text (Publishers DOI)
Affiliation
University of Antwerp
Abstract
Four new methoxy-substituted derivatives of E,E-2,5-bis(2-phenylethenyl)pyrazine have been synthesized. The supramolecular structures of the resulting set of five polymorphs have been studied using single-crystal X-ray diffraction to gauge the influence of the position of the methoxy groups on the organization of the molecules in the solid state, as part of an attempt to dispense with the particular polymorphism of the parent compound. The crystal packing patterns were analyzed in terms of the two pyrazine-based synthons found in the parent compounds crystal structure, the πpyrazine···πphenyl stacking synthon, and the pyrazine hydrogen-bonded synthon, as well as in terms of weak intermolecular interactions such as CH···O, CH···N, and CH···π. The analysis shows that the introduction of methoxy groups in positions other than only the para position of the peripheral benzene rings successfully switches off the two synthons seen in the parent compound and that the new compounds adopt other packing strategies, based on methoxy···methoxy and −OCH3···π contacts. Polymorphism, however, remains.
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