Abstract
The asymmetric unit of the title compound, C23H28O4, comprises two half-mol-ecules, with the other half of each mol-ecule being completed by the application of twofold rotation symmetry. The two completed mol-ecules both have a V-shaped appearance but differ in their conformations. In the crystal, each independent mol-ecule forms chains extending parallel to the b axis with its symmetry-related counterparts through C-H⋯π(ring) inter-actions. Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (65.4%), H⋯C/C⋯H (21.8%) and H⋯O/O⋯H (12.3%) inter-actions. Optimized structures using density functional theory (DFT) at the B3LYP/6-311 G(d,p) level are compared with the experimentally determined mol-ecular structures in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.
Highlights
Eugenol (4-allyl-2-methoxyphenol) is the main active constituent of clove oil (75–90%) from various plants (Patra & Saxena, 2010)
With respect to the biological applications of eugenol 4-allyl-2-methoxyphenol derivatives, it has been shown that these compounds possess potent antimicrobial (Eyambe et al, 2011), antioxidant (Nam & Kim, 2013; Mahapatra et al, 2009; Eyambe et al, 2011), antiviral (Sun et al, 2016), anti-inflammatory (Fonseca et al, 2016), antidiabetic and anti-leishmania properties
As a continuation of our research devoted to the study of oalkylation reactions involving eugenol derivatives, we report the synthesis, molecular and crystal structures of the title compound, (I)
Summary
Eugenol (4-allyl-2-methoxyphenol) is the main active constituent of clove oil (75–90%) from various plants (Patra & Saxena, 2010). The 4-allyl-2-methoxyphenol core has several active sites and provides a great responsiveness, making it an excellent precursor in the syntheses of new heterocyclic compounds (Araujo et al, 2010; Xu et al, 2006) and for the development of drugs (Sticht & Smith, 1971). With respect to the biological applications of eugenol 4-allyl-2-methoxyphenol derivatives, it has been shown that these compounds possess potent antimicrobial (Eyambe et al, 2011), antioxidant (Nam & Kim, 2013; Mahapatra et al, 2009; Eyambe et al, 2011), antiviral (Sun et al, 2016), anti-inflammatory (Fonseca et al, 2016), antidiabetic and anti-leishmania (de Morais et al, 2014) properties. As a continuation of our research devoted to the study of oalkylation reactions involving eugenol derivatives, we report the synthesis, molecular and crystal structures of the title compound, (I). 311 G(d,p) level for comparison with the experimentally determined molecular structure
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