Crystal structure of 1-benzoyl-2,7-dimethoxy-8-(3,5-dimethylbenzoyl) naphthalene: Head-to-head fashioned molecular motif for accumulating weak non-classical hydrogen bonds

Yokoyama, Takeshi; Mido, Takahiro; Takahara, Genta; Ogata, Kazuhiro; Chwojnowska, Elżbieta; Yonezawa, Noriyuki; Okamoto, Akiko

doi:10.5155/eurjchem.8.2.188-194.1572

Cited by 2 publications

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References 25 publications

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“…Of note, recent work has expanded the traditional definition of a hydrogen bond to include a greater variety of hydrogen bond donors, as long as the atom directly attached to the participating hydrogen has significant electronegative character. 205 Hydrogen bonding under this expanded definition has been reported between a C−H bond and an iodide anion, 206 between molybdenum and a phenol proton, 207 between an sp 3 -hybridized C−H proton and aromatic ring, 208 and between carboranes and aromatic rings. 209 Some structural motifs typically used in hydrogen bonding include squaramides, 211 ureas, 212 and thioureas.…”

Section: Underlying Principles Of Chemosensors 21 Non-covalent Intera...mentioning

confidence: 99%

Supramolecular Luminescent Sensors

2018

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There is great need for stand-alone luminescence-based chemosensors that exemplify selectivity, sensitivity, and applicability and that overcome the challenges that arise from complex, real-world media. Discussed herein are recent developments toward these goals in the field of supramolecular luminescent chemosensors, including macrocycles, polymers, and nanomaterials. Specific focus is placed on the development of new macrocycle hosts since 2010, coupled with considerations of the underlying principles of supramolecular chemistry as well as analytes of interest and common luminophores. State-of-the-art developments in the fields of polymer and nanomaterial sensors are also examined, and some remaining unsolved challenges in the area of chemosensors are discussed. CONTENTS 4.4. Explosives 4.5. Pharmaceutical Agents 4.6. Biologically Relevant 4.6.1. Adenosine Triphosphate (ATP)

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Section: Underlying Principles Of Chemosensors 21 Non-covalent Intera...mentioning

confidence: 99%

Supramolecular Luminescent Sensors

2018

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“…The authors reported single molecular structures and the structural features of the molecular packing structures for roughly ninety compounds having 1,8-diaroylated naphthalene skeletons or the homologous/analogous structures via the Cambridge Structure Database (CSD). [15][16][17][18] There are two common features in the crystals of 1,8diaroylated naphthalene compounds, 1) two aroyl groups are non-coplanarly located to the 2,7-dialkoxynaphthalene core and oriented in an opposite direction with a few exceptional compounds bearing unidirectional-alignment of aroyl groups and 2) the molecular packing of 1,8-diaroylated 2,7dialkoxynaphthalene compounds are mainly stabilized by weak hydrogen bonds, i.e., four kinds of non-covalent bonding interactions, ( frequency. The features can be interpreted that the noncoplanarly accumulated aromatic rings structure disturbs formation of strong π…π stacking interactions.…”

Section: Introductionmentioning

confidence: 99%

Dimeric Molecular Aggregation Motif in Crystal of 2,7-Diethoxy-1-(4-Nitrobenzoyl)naphthalene: Correlation of Single Molecular Structure, Molecular Accumulation Structure and Non-Covalent-Bonding Interactions

Ohisa

Saeki

Shiomichi

et al. 2018

ECB

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Crystal structure of 2,7-diethoxy-1-(4-nitrobenzoyl)naphthalene C21H19NO5, is reported and discussed on the characteristics of the spatial organization of single molecule and molecular aggregation as contrasted with a homologous compound. The molecular structures of these compounds differ only in the kind of alkoxy group of 2,7-positions of the naphthalene rings, i.e., ethoxy groups for title compound and methoxy groups for homologue. In single molecular crystal structures of these compounds, 4-nitrobenzoyl group is non-coplanarly attached to the naphthalene ring. The molecules exhibit axial chirality, with either R or S stereogenic axis. The two pairs of the enantiomeric molecules are related by twofold helical axis in the asymmetric unit of P21/n space group for title compound and P21/c one for homologue, showing the number of molecules (Z) is four for both compounds. In their molecular packing structures, (R)-and (S)enantiomers are connected to each other by … stacking interactions, forming centrosymmetric dimeric molecular aggregates. However, the aggregation structures of the dimers are apparently different between title compound and homologue. The dimeric units of title compound are stacked into columnar structure with (sp 2)C-H…O=C non-classical hydrogen bonds between identical enantiomers along aaxis. The columns are connected by (sp 2)C-H…OEt non-classical hydrogen bonds between identical enantiomers along c-axis to give sheet-like aggregation spreading on ac-plane. The sheets are piled up through (sp 3)C-H… non-classical hydrogen bonds between opposite enantiomeric molecules of next dimeric aggregates along b-axis giving layers. On the other hand, the dimeric molecular aggregates of homologue are connected into flattish column by (sp 3)C-H…O=C non-classical hydrogen bonds and (sp 3)C-H… nonclassical hydrogen bonds between identical enantiomers. The columns are linked into waving plate through weak (sp 2)C-H… nonclassical hydrogen bonds. In title compound, difference between … stacking interactions and non-classical hydrogen bonds is smaller than homologue in contribution to the whole of molecular packing structure.

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Crystal structure of 1-benzoyl-2,7-dimethoxy-8-(3,5-dimethylbenzoyl) naphthalene: Head-to-head fashioned molecular motif for accumulating weak non-classical hydrogen bonds

Cited by 2 publications

References 25 publications

Supramolecular Luminescent Sensors

Supramolecular Luminescent Sensors

Dimeric Molecular Aggregation Motif in Crystal of 2,7-Diethoxy-1-(4-Nitrobenzoyl)naphthalene: Correlation of Single Molecular Structure, Molecular Accumulation Structure and Non-Covalent-Bonding Interactions

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