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Mol-ecular structure, DFT studies and UV-Vis absorption of two new linear fused ring chalcones: (E)-1-(anthracen-9-yl)-3-(2-meth-oxy-phen-yl)prop-2-en-1-one and (E)-1-(anthracen-9-yl)-3-(3-fluoro-4-meth-oxy-phen-yl)prop-2-en-1-one.

ABSTRACT: The title compounds, C24H18O2 and C24H17FO2, were synthesized using the Claisen-Schmidt condensation method and characterized by UV-Vis spectroscopy. Weak inter-molecular C-H⋯O, C-H⋯π and π-π hydrogen-bonding inter-actions help to stabilize the crystal structures of both compounds. The geometrical parameters obtained from the mol-ecular structure were optimized using density functional theory (DFT) calculations at the B3LYP/6-311++G(d,p) level, showing a good correlation with the experimental results. The small HOMO-LUMO energy gaps of 3.11 and 3.07 eV enhances the non-linear responses of these mol-ecular systems.

SUBMITTER: Zainuri DA

PROVIDER: S-EPMC6072983 | biostudies-literature |

REPOSITORIES: biostudies-literature

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(E)-1-(3,5-Di-meth-oxy-phen-yl)-3-(3-meth-oxy-phen-yl)prop-2-en-1-one.

Project description:In the title mol-ecule, C18H18O4, the C=C bond of the central enone group adopts a trans conformation. The relative conformation of the C=O and C=C bonds is s-cisoid. The dihedral angle between the planes of the benzene rings is 29.49 (12)°. In the crystal, weak C-H⋯O hydrogen bonds link the mol-ecules into chains along [010].

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(Z)-3-(Anthracen-9-yl)-1-(2-eth-oxy-phen-yl)prop-2-en-1-one.

Project description:The mol-ecule of the title chalcone, C(25)H(20)O(2), consisting of 2-eth-oxy-phenyl and anthracene rings bridged by a prop-2-en-1-one unit, is twisted and exists in the Z configuration with respect to the central C=C bond. The dihedral angle between the benzene and anthracene rings is 78.17 (9)°. The propene unit makes dihedral angles of 44.5 (2) and 81.1 (2)° with the benzene and anthracene rings, respectively. The eth-oxy substituent is almost coplanar with the attached benzene ring [C-O-C-C torsion angle = 178.57 (19)°]. In the crystal, mol-ecules are linked into chains along the a axis by weak C-H⋯O inter-actions. The crystal structure is further stabilized by C-H⋯π inter-actions.

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(E)-1-(4-Meth-oxy-phen-yl)-3-(3,4,5-trimeth-oxy-phen-yl)prop-2-en-1-one.

Project description:The title compound, C(19)H(20)O(5), was synthesized by reaction of 4-meth-oxy-acetophenone and 3,4,5-trimeth-oxy-benzaldehyde. The aromatic rings form a dihedral angle of 36.39?(7)°. Two intramolecular C-H?O hydrogen bonds occur. The crystal packing features weak C-H?O inter-actions.

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(E)-1-(4-Meth-oxy-phen-yl)-3-(2,4,6-trimeth-oxy-phen-yl)prop-2-en-1-one.

Project description:In the title compound, C(19)H(20)O(5), the dihedral angle between the two aromatic rings is 18.23 (4)°. The crystal structure exhibits only weak C-H⋯π and C-H⋯O contacts between the mol-ecules.

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(E)-3-(3,5-Dimeth-oxy-phen-yl)-1-(2-meth-oxy-phen-yl)prop-2-en-1-one.

Project description:In the title mol-ecule, C18H18O4, the dihedral angle between the benzene rings is 52.52 (7)°. The C=C bond of the central enone group adopts a trans conformation. The relative conformation of the two double bonds in the enone group is s-transoid. In the crystal, mol-ecules are linked by pairs of weak C-H⋯O hydrogen bonds, forming inversion dimers.

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(E)-1-[2-Hy-droxy-4,6-bis-(meth-oxy-meth-oxy)phen-yl]-3-[3-meth-oxy-4-(meth-oxy-meth-oxy)phen-yl]prop-2-en-1-one.

Project description:The title compound, C(22)H(26)O(9), crystallizes with two independent mol-ecules in the asymmetric unit in which the dihedral angles between the two benzene rings are 21.4?(2) and 5.1?(2)°. An intra-molecular O-H?O hydrogen bond occurs in each mol-ecule. Inter-molecular C-H?O hydrogen bonds stabilize the crystal structure.

| S-EPMC3247344 | biostudies-literature

(E)-1-(2-Hy-droxy-6-meth-oxy-phen-yl)-3-(2,4,6-tri-meth-oxy-phen-yl)prop-2-en-1-one.

Project description:In the title mol-ecule, C19H20O6, the conformation about the C=C bond of the central enone group is E. The dihedral angle formed by the benzene rings is 11.6?(2)°. The hy-droxy group is involved in an intra-molecular O-H?O hydrogen bond. In the crystal, weak C-H?O hydrogen bonds link the mol-ecules into chains along [010].

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(E)-1-(4-Bromo-phen-yl)-3-(2-meth-oxy-phen-yl)prop-2-en-1-one.

Project description:In the title compound, C(16)H(13)BrO(2), the dihedral angle between the mean planes of the meth-oxy- and bromo-substituted benzene rings is 24.6?(1)°. The angles between the mean plane of the prop-2-en-1-one group and the 4-bromo-phenyl and 2-meth-oxy-phenyl ring planes are 18.8?(1) and 6.0?(1)°, respectively.

| S-EPMC3007412 | biostudies-literature

(2E)-1-(2-Bromo-phen-yl)-3-(4-meth-oxy-phen-yl)prop-2-en-1-one.

Project description:In the title compound, C(16)H(13)BrO(2), two benzene rings form a dihedral angle of 44.3?(9)°. In the crystal, weak inter-molecular C-H?O hydrogen bonds link the mol-ecules into chains propagating in [010]. The crystal packing also exhibits short Br?Br contacts of 3.4787?(8)?Å. A comparison of the DFT-optimized gas-phase mol-ecular geometry with that in the crystal structure revealed only small differences.

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(E)-1-Ferrocenyl-3-(2-meth-oxy-phen-yl)prop-2-en-1-one.

Project description:The structure of the title compound, [Fe(C5H5)(C15H13O2)], consists of a ferrocenyl moiety and a 2-meth-oxy-phenyl group linked through a prop-2-en-1-one spacer in an E conformation. In the ferrocene unit, the substituted cyclo-penta-dienyl (Cps) ring and the unsubstituted cyclo-penta-dienyl ring (Cp) are almost parallel to one another [dihedral angle = 1.78 (14)°], and the Cp and Cps rings are in a gauche conformation. The benzene ring is twisted by 10.02 (14) and 11.38 (11)° with respect to the Cp and Cps rings, respectively. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds into supra-molecular chains running along the b-axis direction.

| S-EPMC3998481 | biostudies-literature

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