Reversible ArSE Aroylation of Naphthalene Derivatives

Okamoto, Akiko; Yonezawa, Noriyuki

doi:10.1246/cl.2009.914

Cited by 87 publications

(85 citation statements)

References 15 publications

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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%

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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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Section: Methodsmentioning

confidence: 99%

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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“…For the formation reaction of aroylated naphthalene compounds via electrophilic aromatic aroylation of 2,7-dimethoxynaphthalene, see: Okamoto & Yonezawa (2009). For related structures, see: Muto et al (2010); Nakaema et al (2007Nakaema et al ( , 2008; Watanabe et al (2010a,b).…”

Section: Related Literaturementioning

confidence: 99%

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

Nishijima¹,

Kataoka²,

Nagasawa³

et al. 2010

Acta Cryst E

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The title compound {systematic name: [8-(4-aminobenzoyl)-2,7-dimethoxynaphthalen-1-yl](4-aminophenyl)methanone}, C26H22O4N2, possesses crystallographically imposed twofold symmetry, with two C atoms lying on the rotation axis. In the crystal, the molecules interact through intermolecular N—H⋯O hydrogen bonds between the amino and methoxy groups on the naphthalene ring systems and N—H⋯π interactions between the amino groups and the naphthalene rings. Furthermore, weak C—H⋯O hydrogen bonds and π–π stacking interactions between the benzene rings are observed. The centroid–centroid and interplanar distances between the benzene rings of the aroyl group and the naphthalene ring systems of adjacent molecules are 3.6954 (8) and 3.2375 (5) Å, respectively. The dihedral angle between the mean planes of the benzene ring and the naphthalene ring system is 83.59 (5)°. The benzene ring and the carbonyl group in the benzoyl unit are almost coplanar [C—C—C—O torsion angle = 175.91 (10)°].

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“…From this point of view, the naphthalene derivatives having aroyl groups at peri-positions, i.e., 1-aroyland 1,8-diaroylnaphthalene derivatives, are one of the good models for analysing non-covalent bonding interactions in crystal. Recently, the authors have found highly effective diaroylation at peri (1,8)-positions of 2,7-dialkoxynaphthalene [10,11]. Furthermore, functional group interconversion of 2-and/or 7-alkoxy group to hydroxyl group is also achievable [12].…”

Section: Introductionmentioning

confidence: 99%