Some chalcones derived from thiophene-3-carbaldehyde: synthesis and crystal structures

Acta Crystallographica Section E: Crystallographic Communications

卷:75

Luc Van Meervelt¹  Thuan Dang Thanh²  Thanh Phung Ngoc²  Duong Tran Thi Thuy²  Trung Vu Quoc²  Chinh Nguyen Thuy³  Vuong Nguyen Thien³ 

[1] Department of Chemistry, KU Leuven, Biomolecular Architecture, Celestijnenlaan 200F, Leuven (Heverlee), B-3001, Belgium;

[2] Faculty of Chemistry, Hanoi National University of Education, 136 Xuan Thuy, Cau Giay, Hanoi, Vietnam;

[3] Institute for Tropical Technology, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Cau Giay, Hanoi, Vietnam;

关键词: crystal structure;    α,β-unsaturated carbonyl;    chalcone;    thiophene;    Hirshfeld analysis;   

DOI  :  10.1107/S2056989019007503

来源: DOAJ

【 摘 要 】

The synthesis, spectroscopic data and crystal and molecular structures of four 3-(3-phenylprop-1-ene-3-one-1-yl)thiophene derivatives, namely 1-(4-hydroxyphenyl)-3-(thiophen-3-yl)prop-1-en-3-one, C13H10O2S, (1), 1-(4-methoxyphenyl)-3-(thiophen-3-yl)prop-1-en-3-one, C14H12O2S, (2), 1-(4-ethoxyphenyl)-3-(thiophen-3-yl)prop-1-en-3-one, C15H14O2S, (3), and 1-(4-bromophenyl)-3-(thiophen-3-yl)prop-1-en-3-one, C13H9BrOS, (4), are described. The four chalcones have been synthesized by reaction of thiophene-3-carbaldehyde with an acetophenone derivative in an absolute ethanol solution containing potassium hydroxide, and differ in the substituent at the para position of the phenyl ring: –OH for 1, –OCH3 for 2, –OCH2CH3 for 3 and –Br for 4. The thiophene ring in 4 was found to be disordered over two orientations with occupancies 0.702 (4) and 0.298 (4). The configuration about the C=C bond is E. The thiophene and phenyl rings are inclined by 4.73 (12) for 1, 12.36 (11) for 2, 17.44 (11) for 3 and 46.1 (6) and 48.6 (6)° for 4, indicating that the –OH derivative is almost planar and the –Br derivative deviates the most from planarity. However, the substituent has no real influence on the bond distances in the α,β-unsaturated carbonyl moiety. The molecular packing of 1 features chain formation in the a-axis direction by O—H...O contacts. In the case of 2 and 3, the packing is characterized by dimer formation through C—H...O interactions. In addition, C—H...π(thiophene) interactions in 2 and C—H...S(thiophene) interactions in 3 contribute to the three-dimensional architecture. The presence of C—H...π(thiophene) contacts in the crystal of 4 results in chain formation in the c-axis direction. The Hirshfeld surface analysis shows that for all four derivatives, the highest contribution to surface contacts arises from contacts in which H atoms are involved.

【 授权许可】

Unknown