1,8-Bis(4-chlorobenzoyl)-2,7-dimethoxynaphthalene

Nakaema, Kosuke; Okamoto, Akiko; Noguchi, Keiichi; Yonezawa, Noriyuki

doi:10.1107/s1600536807045114

Cited by 17 publications

(5 citation statements)

References 9 publications

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“…Analogous aroylated unsymmetrical naphthalene compounds, for example, 1,8-bis(4-chlorobenzoyl)-2-hydroxy-7-methoxynaphthalene and 1,8-bis(4-chlorobenzoyl)-2,7-dimethoxynaphthalene (Nakaema et al, 2007), have two aroyl groups at the 1,8positions of the naphthalene ring system. The two 4-chlorobenzoyl groups have the same orientation with respect to the naphthalene ring core in 1,8-bis(4-chlorobenzoyl)-2-hydroxy-7-methoxynaphthalene, while they are in opposite directions in 1,8-bis(4-chlorobenzoyl)-2,7-dimethoxynaphthalene.…”

Section: Structural Commentarymentioning

confidence: 99%

Crystal structure and Hirshfeld surface analysis of 2-hydroxy-7-methoxy-1,8-bis(2,4,6-trichlorobenzoyl)naphthalene

et al. 2019

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In the title compound, C25H12Cl6O4, the two carbonyl groups are oriented in a same direction with respect to the naphthalene ring system and are situated roughly parallel to each other, while the two 2,4,6-trichlorobenzene rings are orientated in opposite directions with respect to the naphthalene ring system: the carbonyl C—(C=O)—C planes subtend dihedral angles of 45.54 (15) and 30.02 (15)° to the naphthalene ring system are. The dihedral angles formed by the carbonyl groups and the benzene rings show larger differences, the C=O vectors being inclined to the benzene rings by 46.39 (16) and 79.78 (16)°. An intramolecular O—H...O=C hydrogen bond forms an S(6) ring motif. In the crystal, no effective intermolecular hydrogen bonds are found; instead, O...Cl and C...Cl close contacts are observed along the 21 helical-axis direction. The Hirshfeld surface analysis reveals several weak interactions, the major contributor being Cl...H/H...Cl contacts.

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Section: Structural Commentarymentioning

confidence: 99%

Crystal structure and Hirshfeld surface analysis of 2-hydroxy-7-methoxy-1,8-bis(2,4,6-trichlorobenzoyl)naphthalene

et al. 2019

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“…Recently, the authors' group has revealed that diaroylation at 1,8-positions of 2,7-dimethoxynaphthalene smoothly proceeds [16,17]. According to X-ray crystal structural study, the obtained 1,8-diaroylnaphthalene has unique non-coplanar alignment of aromatic rings [18]. The curious reversible aroylation behavior of the naphthalene derivative [16] and chemospecific and regioselective ethereal alkyl-oxygen bond cleavage reaction of aroylated naphthalenes [19] can be explained on the basis of the structural features of the aroylated naphthalenes.…”

Section: Introductionmentioning

confidence: 99%

Crystal Structure and Solution Structural Dynamic Feature of 1,8-Dibenzoyl-2,7-Dimethoxynaphthalene

Okamoto¹,

Watanabe²,

Nakaema³

et al. 2012

CSTA

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The crystal structure and the dynamic feature of molecular structure in solution for 1,8-dibenzoyl-2,7-dimethoxynaphthalene are revealed by X-ray crystallographic analysis and VT-NMR measurements. In crystal, the molecule of the title compound is located on a twofold rotation axis. The two benzoyl groups are situated in an opposite direction. The dihedral angle between the mean planes of the phenyl ring and the naphthalene ring system is 80.25(6)˚. The benzene ring and carbonyl moiety in each benzoyl group are almost coplanar. The molecular packing is stabilized by weak C-H…O hydrogen bonds and a π-π stacking interaction between the benzene rings [centroid-centroid and interplanar distances of 3.6383(10) and 3.294 Å, respectively]. In solution, the temperature-dependent rotation behavior of the C-C bond between the benzene ring and the ketonic carbonyl group has been observed by 1 H VT-NMR measurements. Furthermore, comparison of the C-C bond rotation behavior between the benzene ring and the carbonyl group with 1-benzoyl-2,7-dimethoxynaphthalene has clarified that the C-C bond between the ketonic carbonyl group and the naphthalene ring rotates slower than the 1,8-dibenzoylated homologue.

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“…22 Synthetic methods and spectral data for the precursor, 1,8-bis(4-chlorobenzoyl)-2,7-dimethoxynaphthalene, have been reported in literature. 11,12,20 Measurements 1 H NMR spectra were recorded on a JEOL JNM-AL300 spectrometer (300 MHz). Chemical shifts are expressed in ppm relative to internal standard of Me4Si (δ 0.00).…”

Section: Methodsmentioning

confidence: 99%

“…The authors' recent work has focused on peri-aroylnaphthalene compounds and the homologous/analogous substances. [11][12][13][14][15][16][17][18][19][20] According to the X-ray crystal structural analyses of ninety peri-aroylnaphthalene compounds, the two aroyl groups are non-coplanarly situated to the naphthalene ring and ordinary oriented in an opposite direction (anti-orientation). The molecular packing of peri-aroylnaphthalene compounds are mainly stabilized by cooperation of several kinds of weak non-covalent-bonding interactions, i.e., four kinds of nonclassical hydrogen bonds, (sp 2 )C-H···O=C hydrogen bond, (sp 3 )C-H···O=C hydrogen bond, (sp 3 )C-H···OR hydrogen bond, and C-H···π hydrogen-bonding interaction, and π···π stacking interaction are observed in decreasing order of frequency.…”

Section: Introductionmentioning

confidence: 99%

Crystal Structure of (1r,2s)-1,2-Bis(4-Chlorophenyl)-3,8-Dimethoxyacenaphthene-1,2-Diol: Tetrameric String of Four Conformers Connected by Classical Hydrogen Bonds and Molecular Accumulation Alignment by Linking of the Tetramers With the Aid of Non-Classi

Mido

Iitsuka

Yokoyama

et al. 2017

ECB

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Keywords: S-shaped tetramer composed of four conformers, pseudo-centrosymmetricity, classical hydrogen bonds, non-classical hydrogen bondsCrystal structure of (1R,2S)-1,2-bis(4-chlorophenyl)-3,8-dimethoxyacenaphthene-1,2-diol, C26H20O4Cl2, is reported and discussed from the viewpoints of characteristics in spatial organization, i.e., single molecular structures of four conformers, tetrameric aggregates, and higher ordered structures, with clarification of a classical and two non-classical hydrogen bonding interactions as the structure determining interactions. The title compound crystallizes with four independent molecules (conformers G, B, R, and Y) in the asymmetric unit. Furthermore, each independent molecule displays a meso configuration, with one 4-chlorophenyl group R and the other S. The four molecules are related by inversion center in the asymmetric unit of P-1 space group, exhibiting the number of molecules is eight, Z = 8. Single molecular structure of each conformer shows that the two benzene rings are bonded with large dihedral angles against the naphthalene plane and the two phenyl rings are oriented in the same direction with respect to the naphthalene ring plane (syn-orientation). The four conformers are classified into two groups according to overlapping feature of phenyl rings, i.e., conformers G and Y have larger slippage of the phenyl rings than conformers B and R. In the molecular packing, four conformers Y, B, R, and G are connected by classical O-H…O(H) hydrogen bonds in head-to-head fashion forming S-shaped tetramer. Tetramers composed of four conformers are stacked into columnar structure along a-axis through non-classical C-H…Cl hydrogen bonds between conformers G. The columns are linked into a sheet structure by non-classical C-H…Cl hydrogen bonds between conformers G and Y along ab-diagonal. The waved sheets are interlocked by two types of non-classical C-H… hydrogen bonds forming the stripe structure along c-axis, i.e., non-classical C-H… hydrogen bonds between conformers R and Y, and those between conformers B and G.

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1,8-Bis(4-chlorobenzoyl)-2,7-dimethoxynaphthalene

Cited by 17 publications

References 9 publications

Crystal structure and Hirshfeld surface analysis of 2-hydroxy-7-methoxy-1,8-bis(2,4,6-trichlorobenzoyl)naphthalene

Crystal structure and Hirshfeld surface analysis of 2-hydroxy-7-methoxy-1,8-bis(2,4,6-trichlorobenzoyl)naphthalene

Crystal Structure and Solution Structural Dynamic Feature of 1,8-Dibenzoyl-2,7-Dimethoxynaphthalene

Crystal Structure of (1r,2s)-1,2-Bis(4-Chlorophenyl)-3,8-Dimethoxyacenaphthene-1,2-Diol: Tetrameric String of Four Conformers Connected by Classical Hydrogen Bonds and Molecular Accumulation Alignment by Linking of the Tetramers With the Aid of Non-Classi

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