Crystal structures of three 3,4,5-trimethoxybenzamide-based derivatives

• Type: Article in International Scientific Journal
• Date: 2016

Authors

Gomes, LR (Author) Other; Low, JN (Author) Other; Oliveira, C (Author) Other; Fernando Cagide (Author) FCUP; Fernanda Borges (Author) FCUP

Journal

Title: Acta Crystallographica Section E: Crystallographic Communications

Vol. 72

Pages: 675-+

Publisher: International Union of Crystallography

Indexing

ISI Web of Knowledge - 3 Citations

Scopus - 3 Citations

Other information

Authenticus ID: P-00K-FHK

DOI: 10.1107/s2056989016005958

Abstract (EN): The crystal structures of three benzamide derivatives, viz. N-(6-hydroxyhexyl)-3,4,5-trimethoxybenzamide, C16H25NO5, (1), N-(6-anilinohexyl)-3,4,5-trimethoxybenzamide, C22H30N2O4, (2), and N-(6,6-diethoxyhexyl)-3,4,5-trimethoxybenzamide, C20H33NO6, (3), are described. These compounds differ only in the substituent at the end of the hexyl chain and the nature of these substituents determines the differences in hydrogen bonding between the molecules. In each molecule, the m-methoxy substituents are virtually coplanar with the benzyl ring, while the p-methoxy substituent is almost perpendicular. The carbonyl O atom of the amide rotamer is trans related with the amidic H atom. In each structure, the benzamide N-H donor group and O acceptor atoms link the molecules into C(4) chains. In 1, a terminal -OH group links the molecules into a C(3) chain and the combined effect of the C(4) and C(3) chains is a ribbon made up of screw related R-2(2) (17) rings in which the center dot center dot center dot O-H center dot center dot center dot chain lies in the centre of the ribbon and the trimethoxybenzyl groups forms the edges. In 2, the combination of the benzamide C(4) chain and the hydrogen bond formed by the terminal N-H group to an O atom of the 4-methoxy group link the molecules into a chain of R-2(2) (17) rings. In 3, the molecules are linked only by C(4) chains.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 24