ABSTRACT: The title disubstituted naphthalene-1,4-dione, C(24)H(16)Cl(2)O(2), has the two chloro-benzyl substituents related by a non-crystallographic twofold rotation axis, generating a chiral conformation; both enantiomers are present. The two chlorobenzene rings are nearly perpendicular to the fused ring system, making angles of 88.8?(1) and 77.5?(1)° with it.
Project description:The title compound, C(11)H(8)O(3), was isolated from Impatiens balsamina plants (balsam, LIB) grown in our laboratory. The two six-membered rings of the naphthalene-1,4-dione unit are coplanar [maximum deviation = 0.009?(1)?Å]. The O and C atoms of the meth-oxy substituent also lie close to the naphthalene plane, with deviations of 0.0090?(2) and 0.047?(2)?Å, respectively.
Project description:The purpose of this study was to identify transcripts differentially expressed in zebrafish embryos exposed to two oxygenated PAHs, 1,9-benz-10-anthrone and benzanthracene-7,12-dione, which cause abnormal development. We used RNA-seq (Illumina HiSeq) to identify mRNA profiles of whole zebrafish embryos exposed to 10 μM 1,9-benz-10-anthrone, benzanthracene-7,12-dione or vehicle control (1% DMSO) from 6-48 hours post fertilization
Project description:The asymmetric unit of the title co-crystal, C10H5BrO2·C14H8O4 [systematic name: 2-bromo-1,4-di-hydro-naphthalene-1,4-dione-1,8-dihy-droxy-9,10-di-hydro-anthracene-9,10-dione (1/1)], features one mol-ecule of each coformer. The 2-bromo-naphtho-quinone mol-ecule is almost planar [r.m.s deviation of the 13 non-H atoms = 0.060?Å, with the maximum deviations of 0.093?(1) and 0.099?(1)?Å being for the Br atom and a carbonyl-O atom, respectively]. The 1,8-di-hydroxy-anthra-quinone mol-ecule is planar (r.m.s. deviation for the 18 non-H atoms is 0.022?Å) and features two intra-molecular hy-droxy-O-H?O(carbon-yl) hydrogen bonds. Dimeric aggregates of 1,8-di-hydroxy-anthra-quinone mol-ecules assemble through weak inter-molecular hy-droxy-O-H?O(carbon-yl) hydrogen bonds. The mol-ecular packing comprises stacks of mol-ecules of 2-bromo-naphtho-quinone and dimeric assembles of 1,8-di-hydroxy-anthra-quinone with the shortest ?-? contact within a stack of 3.5760?(9)?Å occurring between the different rings of 2-bromo-naphtho-quinone mol-ecules. The analysis of the Hirshfeld surface reveals the importance of the inter-actions just indicated but, also the contribution of additional C-H?O contacts as well as C=O?? inter-actions to the mol-ecular packing.
Project description:A series of ten push-pull chromophores comprising 1H-cyclopenta[b]naphthalene-1,3(2H)-dione as the electron-withdrawing group have been designed, synthesized, and characterized by UV-visible absorption and fluorescence spectroscopy, cyclic voltammetry and theoretical calculations. The solvatochromic behavior of the different dyes has been examined in 23 solvents and a positive solvatochromism has been found for all dyes using the Kamlet-Taft solvatochromic relationship, demonstrating the polar form to be stabilized in polar solvents. To establish the interest of this polyaromatic electron acceptor only synthesizable in a multistep procedure, a comparison with the analog series based on the benchmark indane-1,3-dione (1H-indene-1,3(2H)-dione) has been done. A significant red-shift of the intramolecular charge transfer band has been found for all dyes, at a comparable electron-donating group. Parallel to the examination of the photophysical properties of the different chromophores, a major improvement of the synthetic procedure giving access to 1H-cyclopenta[b]naphthalene-1,3(2H)-dione has been achieved.
Project description:The title mol-ecule, C(22)H(16)ClNO(5), was obtained by the reaction of (E)-ethyl 3-(3-chloro-phen-yl)-2-cyano-acrylate and 2-hydroxy-naphthalene-1,4-dione catalysed by triethylamine in ethanol. In the crystal structure, the chlorobenzene ring makes a dihedral angle of 88.63?(4)° with the fused ring system. The six-membered ring formed by an intra-molecular N-H?O hydrogen bond is almost planar. The crystal packing is stabilized by N-H?O hydrogen bonds.
Project description:In the structure of the title compound, C14H12O3, the substituent side chain, in which the H atoms of both methyl groups are disordered over six equivalent sites, lies outside of the plane of the naphthalene-dione ring. The ring-to-chain C-C-C-C torsion angles are 50.7?(3), -176.6?(2) and 4.9?(4)°. An intra-molecular meth-yl-hy-droxy C-H?O hydrogen bond is present. In the crystal, mol-ecules are primarily connected by inter-molecular O-H?O hydrogen bonds, forming a centrosymmetric cyclic dimer motif [graph set R 2 (2)(10)]. Also present is a weak inter-molecular C-H?O hydrogen bond linking the dimers and a weak ?-? ring inter-action [ring centroid separation = 3.7862?(13)?Å], giving layers parallel to (10-3).
Project description:In the title compound, C(15)H(10)FNO(3), the dihedral angle between the isoindoline-1,3-dione and 3-fluoro-4-methyl-phenol groups is 86.88?(8)°. The isoindoline-1,3-dione fragment is almost planar, with an r.m.s. deviation of 0.0154?Å within the group. Inter-molecular C-H?O hydrogen bonds generate C(6) chains running parallel to the  direction.
Project description:In this study, stable hybrid materials (Mt-Fe(III)Phen), made by the ?-oxo Fe(III)-phenanthroline complex [(OH2)3(Phen)FeOFe(Phen)(OH2)3]4+ (Fe(III)Phen) intercalated in different amounts into montmorillonite (Mt), were used as a trap for immobilizing gaseous benzene and naphthalene and their mono chloro-derivatives at 25 and 50 °C. The entrapping process was studied through elemental analysis, magic angle spinning NMR spectroscopy, thermal analysis, and evolved gas mass spectrometry. Naphthalene and 1-chloronaphthalene were found to be immobilized in large amount at both temperatures. Molecular modeling allowed designing of the structure of the interlayer in the presence of the immobilized aromatic molecules. Adsorption is affected by the amount of the Fe complex hosted in the interlayer of the entrapping hybrid materials. On the contrary, under the same conditions, benzene and chlorobenzene were not adsorbed. Thermal desorption of naphthalenes was obtained under mild conditions, and immobilization was found to be reversible at least for 20 adsorption/desorption cycles.
Project description:The title compound, C(14)H(11)N(3)O(3), adopts an E or trans configuration with respect to the C=N bond. In the mol-ecule there is an intra-molecular O-H?N hydrogen bond involving the hy-droxy substituent at the 2-positon of the naphthalene ring and the adjacent methyl-ene-amino N atom. The mol-ecule is roughly planar, the dihedral angle between the naphthalene and imidazolidine-2,4-dione mean planes being 8.4?(1)°. In the crystal, pairs of N-H?O hydrogen bonds link mol-ecules into inversion dimers. These dimers are futher linked via C-H?O inter-actions, forming a three-dimensional network.
Project description:Two new 5,12-disubstituted 2,3-di-ethyl-naphtho-[2,3-g]quinoxaline-6,11-dione compounds were readily synthesized from the commercial dye quinizarin. For 2,3-diethyl-5,12-di-hydroxy-naphtho-[2,3-g]quinoxaline-6,11-dione, (II), C20H16N2O4, the mol-ecule displays a near planar conformation and both hy-droxy groups participate in intra-molecular O-H?O(carbon-yl) hydrogen bonds. In the crystal, ?-? ring inter-actions [minimum ring centroid separation = 3.5493?(9)?Å] form stacks of co-planar mol-ecules down the c axis, while only minor inter-molecular C-H?O inter-actions are present. In contrast, in 2,3-diethyl-5,12-bis-(piperidin-1-yl)naphtho-[2,3-g]quinoxaline-6,11-dione, (IV), C30H34N4O2, which contains two independent, but similar, mol-ecules in the asymmetric unit, the polycyclic cores have a significant twist, with dihedral angles of 29.79?(6) and 29.31?(7)° between the terminal rings and only minor inter-molecular C-H?O hydrogen-bonding inter-actions are present. Electron density associated with additional solvent mol-ecules disordered about a fourfold axis was accounted for using the SQUEEZE procedure in PLATON [Spek (2015 ?). Acta Cryst. C71, 9-18].