(2,7-Dimethoxynaphthalene-1,8-diyl)bis(4-fluorobenzoyl)dimethanone

Watanabe, Shôji; Nagasawa, Atsushi; Okamoto, Akiko; Noguchi, Keiichi; Yonezawa, Noriyuki

doi:10.1107/s1600536810000486

Cited by 19 publications

(16 citation statements)

References 6 publications

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“…7 Based on the X-ray crystal structure analysis, the two aroyl groups of the bis(4-fluorobenzoyl)naphthalene monomer 1 are asymmetrically bent (Figure 1; Supplementary Figure S1 shows the X-ray crystal structure with the detailed crystal information). 19 The interplanar angles between the naphthalene ring and the two benzene ring planes of monomer 1 are 66.88(7)1 and 88.09(6)1, respectively. To our best knowledge, 9,10,20,21 the 1,8-diaroylated naphthalene molecules that have been reported in this study have larger interplanar angles than other homologous molecules, for example, 1,8-diaroylnaphthalene without 2,7-methoxy groups.…”

Section: Resultsmentioning

confidence: 99%

Poly(arylene ether ketone)s composed of a 1,8-diaroylenenaphthalene moiety: a non-coplanarly accumulated aromatic-ring repeating unit

Okamoto

Hijikata

Sakai

et al. 2012

Polym J

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Poly(arylene ether ketone)s composed of a 1,8-diaroylenenaphthalene moiety, which is a non-coplanar accumulated aromaticring unit, were successfully synthesized through the nucleophilic aromatic substitution polycondensation of 1,8-bis (4-fluorobenzoyl)-2,7-dimethoxynaphthalene with several arene diols under mild conditions. The polymers show high glass transition temperatures (T g), poor solubility and good film-forming ability through heat casting.

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Section: Resultsmentioning

confidence: 99%

Poly(arylene ether ketone)s composed of a 1,8-diaroylenenaphthalene moiety: a non-coplanarly accumulated aromatic-ring repeating unit

Okamoto

Hijikata

Sakai

et al. 2012

Polym J

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“…The aromatic rings in this molecule are clarified to be assembled with non-coplanar configuration resulting in partial disruption of π-conjugated ring systems. Recently, we reported the X-ray crystal structures of 1,8-diaroylated 2,7-dimethoxynaphthalenes such as 1,8-bis(4-chlorobenzoyl)-2,7-dimethoxynaphthalene (Nakaema et al, 2007), 1,8-dibenzoyl-2,7-dimethoxynaphthalene (Nakaema et al, 2008), bis(4-bromophenyl) (2,7-dimethoxynaphthalene-1,8-diyl)dimethanone (Watanabe et al, 2010a), (Watanabe et al, 2010b) and 1,8-bis(4-methylbenzoyl)-2,7-dimethoxynaphthalene (Muto et al, in press). As a part of our continuous study on the molecular structures of this kind of homologous molecules, the X-ray crystal structure of title compound, (I), a peri-aroylnaphthalene bearing amino groups, is discussed in this article.…”

Section: Commentmentioning

confidence: 98%

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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“…In the solid state, the molecules of the peri-aroylnaphthalene compounds thus obtained have noncoplanar aromatic rings. The two aroyl groups are attached to the naphthalene ring in a perpendicular fashion and are oriented in opposite directions (Nakaema et al, 2008;Watanabe et al, 2010).…”

Section: Issn 2053-2296mentioning

confidence: 99%

Hydrogen bonding between aromatic H and F groups leading to a stripe structure withR- andS-columns: the crystal structure of (2,7-dimethoxynaphthalen-1-yl)(3-fluorophenyl)methanone and comparison with its 1-aroylnaphthalene analogues

et al. 2015

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In the molecule of (2,7-dimethoxynaphthalen-1-yl)(3-fluorophenyl)methanone, C19H15FO3, (I), the dihedral angle between the plane of the naphthalene ring system and that of the benzene ring is 85.90 (5)°. The molecules exhibit axial chirality, with either an R- or an S-stereogenic axis. In the crystal structure, each enantiomer is stacked into a columnar structure and the columns are arranged alternately to form a stripe structure. A pair of (methoxy)C-H...F hydrogen bonds and π-π interactions between the benzene rings of the aroyl groups link an R- and an S-isomer to form a dimeric pair. These dimeric pairs are piled up in a columnar fashion through (benzene)C-H...O=C and (benzene)C-H...OCH3 hydrogen bonds. The analogous 1-benzoylated compound, namely (2,7-dimethoxynaphthalen-1-yl)(phenyl)methanone [Kato et al. (2010). Acta Cryst. E66, o2659], (II), affords three independent molecules having slightly different dihedral angles between the benzene and naphthalene rings. The three independent molecules form separate columns and the three types of column are connected to each other via two C-H...OCH3 hydrogen bonds and one C-H...O=C hydrogen bond. Two of the three columns are formed by the same enantiomeric isomer, whereas the remaining column consists of the counterpart isomer. In the case of the fluorinated 1-benzoylated naphthalene analogue, namely (2,7-dimethoxynaphthalen-1-yl)(4-fluorophenyl)methanone [Watanabe et al. (2011). Acta Cryst. E67, o1466], (III), the molecular packing is similar to that of (I), i.e. it consists of stripes of R- and S-enantiomeric columns. A pair of C-H...F hydrogen bonds between R- and S-isomers, and C-H...O=C hydrogen bonds between R(or S)-isomers, are also observed. Consequently, the stripe structure is apparently induced by the formation of R...S dimeric pairs stacked in a columnar fashion. The pair of C-H...F hydrogen bonds effectively stabilizes the dimeric pair of R- and S-enantiomers. In addition, the co-existence of C-H...F and C-H...O=C hydrogen bonds makes possible the formation of a structure with just one independent molecule.

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(2,7-Dimethoxynaphthalene-1,8-diyl)bis(4-fluorobenzoyl)dimethanone

Cited by 19 publications

References 6 publications

Poly(arylene ether ketone)s composed of a 1,8-diaroylenenaphthalene moiety: a non-coplanarly accumulated aromatic-ring repeating unit

Poly(arylene ether ketone)s composed of a 1,8-diaroylenenaphthalene moiety: a non-coplanarly accumulated aromatic-ring repeating unit

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

Hydrogen bonding between aromatic H and F groups leading to a stripe structure withR- andS-columns: the crystal structure of (2,7-dimethoxynaphthalen-1-yl)(3-fluorophenyl)methanone and comparison with its 1-aroylnaphthalene analogues

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