Journal
MOLECULAR DIVERSITY
Volume 14, Issue 4, Pages 643-652Publisher
SPRINGER
DOI: 10.1007/s11030-009-9202-4
Keywords
Benzofuroxan derivative; Crystal structure; FT-Raman; Geometry optimization; Mesomeric effect; Antichagasic drug
Categories
Funding
- FAPESP (Fundacao de Amparo a Pesquisa do Estado de Sao Paulo)
- CNPq (Conselho Nacional de Desenvolvimento Cientifico e Tecnologico)
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The crystal structure and the vibrational spectrum of a potential drug for Chagas's disease treatment, the (E)-isomer of phenylethenylbenzofuroxan 1 (5(6)(E)-[(2-phenylethenyl)]benzo[1,2-c]1,2,5-oxadiazole N-oxide), are reported. In order to provide insights into structural relationships, quantum mechanical calculations were employed starting from crystal structure. These results have given theoretical support to state interesting structural features, such as the effect of some intermolecular contacts on the molecule conformation and the electronic delocalization decreasing through atoms of the benzofuroxan moiety. Furthermore, the MOGUL comparative analysis in the Cambridge Structural Database provided additional evidences on these structural behaviors of compound 1. Intermolecular contacts interfere on the intramolecular geometry, as, for instance, on the phenyl group orientation, which is twisted by 12.32(6)A degrees from the ethenylbenzofuroxan plane. The experimental Raman spectrum of compound 1 presents unexpected frequency shift and also anomalous Raman activities. At last, the molecule skeleton deformation and the characteristic vibrational modes were correlated by matching the experimental Raman spectrum to the calculated one.
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