Peri Interactions in Naphthalene Diketones: A Preference for (Z,Z) Conformations

Cohen, Shmuel; Thirumalaikumar, M.; Pogodin, Sergey; Agranat, Israel

doi:10.1023/b:stuc.0000026750.39809.07

Cited by 16 publications

(10 citation statements)

References 8 publications

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“…Colorless single crystals suitable for X-ray diffraction were obtained by recrystallization from ethanol. 13…”

Section: Synthetic Procedures Of the Title Compoundmentioning

confidence: 99%

“…Peri-substituted naphthalenes have also received much attention as unique structured aromatic core compounds for variety of the functional materials [8][9][10][11][12]. Therefore, the structural analyses have been actively performed [13][14][15]. Recently, the authors' group has revealed that diaroylation at 1,8-positions of 2,7-dimethoxynaphthalene smoothly proceeds [16,17].…”

Section: Introductionmentioning

confidence: 99%

“…Chemical shifts are expressed in ppm relative to internal standard of Me 4 Si (δ 0.00). 13 C NMR spectra were recorded on a JEOL JNM-AL300 spectrometer (75 MHz). Chemical shifts are expressed in ppm relative to internal standard of CDCl 3 (δ 77.0).…”

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confidence: 99%

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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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“…Colorless single crystals suitable for X-ray diffraction were obtained by recrystallization from ethanol. 13…”

Section: Synthetic Procedures Of the Title Compoundmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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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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“…Peri-substituted naphthalenes have also received much attention as characteristic structured aromatic core compounds for a variety of functional materials (Mei et al, 2006;Shinamura et al, 2010;Jiang et al, 2010). Therefore, structural analyses have been actively performed (Gore et al, 1980;Cohen et al, 2004;Jing et al, 2005). Recently, we have revealed that diaroylation at the 1-and 8-positions of naphthalene proceeds smoothly (Okamoto & Yonezawa, 2009;Okamoto et al, 2011).…”

Section: Introductionmentioning

confidence: 97%

Head-to-tail square-shaped cyclic hydrogen bonds leading to dimeric aggregates: 1,8-dibenzoyl-2,7-dihydroxynaphthalene and a comparison with its analogous benzoylnaphthalene

et al. 2013

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The title compound, C24H16O4, crystallized with two independent molecules in the asymmetric unit. Both carbonyl groups in these molecules form intramolecular O-H...O=C hydrogen bonds with neighbouring hydroxy groups, affording six-membered cyclic structures. In the crystal, dimeric aggregates arise from two intermolecular O-H···O=C hydrogen bonds between both independent molecules, forming head-to-tail square-shaped cyclic ···O···H···O···H··· hydrogen bonds. These dimeric aggregates are connected into layers in the bc plane by intermolecular (naphthalene)C-H...O=C interactions. On the other hand, the analogous compound bearing methoxy groups at the 2- and 7-positions of the naphthalene ring, namely 1,8-dibenzoyl-2,7-dimethoxynaphthalene [Nakaema et al. (2008). Acta Cryst. E64, o807], forms a three-dimensional molecular network via C-H···O=C and π-π interactions between the benzoyl groups. These results show that the intramolecular O-HvO=C hydrogen bonds in the title compound control the orientations of the benzoyl groups and thus promote the formation of the cyclic intermolecular O-H···O=C interactions involving the same donor and acceptor groups in pairs of molecules.

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“…In the final article of Issue 4, Cohen et al [85] presented the surprising finding that 1,8-diacylnaphthalenes prefer a Z,Z conformation, i.e., the two carbonyl groups are pointing in the same direction. This is explained in terms of the relative sizes of the Os and the groups affixed to the carbonyl carbons.…”

Section: Introductionmentioning

confidence: 97%

Interplay of thermochemistry and structural chemistry, the journal (volume 15, 2004) and the discipline

Stem

Liebman

2006

Struct Chem

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As practiced disciplines, structural chemistry, and thermochemistry need not necessarily be related. Yet such relationships, ranging from minor to very close, can help our overall understanding and detailed analyses of the species and methods under consideration. In the current study, these relations are made more evident from among the contents of the journal "Structural Chemistry" (Vol. 15) for the year 2004. The year's articles have been reviewed, giving to most of those appearing therein a thermochemical commentary, "spin" or "slant." A special emphasis is made on raising questions or noting possible future research topics that arise when looking at the relations noted earlier.

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Peri Interactions in Naphthalene Diketones: A Preference for (Z,Z) Conformations

Cited by 16 publications

References 8 publications

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

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

Head-to-tail square-shaped cyclic hydrogen bonds leading to dimeric aggregates: 1,8-dibenzoyl-2,7-dihydroxynaphthalene and a comparison with its analogous benzoylnaphthalene

Interplay of thermochemistry and structural chemistry, the journal (volume 15, 2004) and the discipline

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