Crystal Structure and Supramolecularity of (E)-4-(4-tert-butylphenyl)but-3-en-2-one




Crystal structure, C—H···O interactions, C—H···π interactions, α,β-unsaturated ketones.

How to Cite

Mahmoud Al-Refai, M. A.-R., & Basem F. Ali*, B. F. A. (2022). Crystal Structure and Supramolecularity of (E)-4-(4-tert-butylphenyl)but-3-en-2-one. Jordan Journal of Chemistry (JJC), 16(3), 99-104. Retrieved from (Original work published November 16, 2021)


The title compound, C14H18O, I, was obtained as a side product during an attempt to synthesize (E)-3-(4-tert-butylphenyl)-1-(2,5-dichlorothiophen-3-yl)prop-2-en-1-one from the reaction of 1-(2,5-dichlorothiophen-3-yl)ethanone and 4-tert-butylbenz­aldehyde and KOH solution in methanol. It turned out that methanol which was used is a mixture of methanol/acetone (80:20%, respectively) and the product was probably generated by direct condensation between 4-tert-butylbenzaldehyde and acetone in presence of KOH. The asymmetric unit of I consists of one independent molecule. The molecule is nearly planar as evidenced by the dihedral angle of 8.05o between the C5–C10/C11 substituted phenyl ring and the but-3-en-2-one unit (O1/C1–C4). In the crystal, C—H···O hydrogen bonds form inversion dimers of molecules, enclosing an R22(8) ring motif that stacks through pairwise C—H···π (ring) interactions.