Synthesis, reactions and thermal properties of endo-5,12: endo-6,11-dietheno-5,5a,6,11,11a,12-hexahydronaphthacene

Lin, Cheng‐Tung; Wang, Nae-Jen; Yeh, Yu-Chen; Chou, Teh‐Chang

doi:10.1016/0040-4020(95)00041-6

Cited by 31 publications

(12 citation statements)

References 43 publications

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“…The π–π interactions are extremely important, due to the indispensable role in physical, chemical, and biological sciences. Various types of the π–π interactions have been investigated structurally and energetically, so far . We have been much interested in the π–π interactions as a factor to control the fine details of structures and to create delicate properties in materials.…”

Section: Introductionmentioning

confidence: 99%

Intramolecular π–π Interactions in Diethanodihydronaphthalene and Derivatives: Dynamic and Static Behavior of the Interactions Elucidated by QTAIM Dual Functional Analysis

2016

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Dynamic and static behavior of the intramolecular p-p interactions between ethylene moieties in diethanodihydronaphthalene (1 a) and the derivatives (2 a-12 a) are elucidated by employing QTAIM-DFA (QTAIM dual functional analysis), which we proposed recently. Total electron energy densities H b (r c ) are plotted versus H b (r c ) -V b (r c )/2 at bond critical points (BCPs) for the interactions in question in QTAIM-DFA, where V b (r c ) are potential energy densities at BCPs. After analysis of the plots, the p-p interactions in 1 a-12 a are all classified by the pure closed shell interactions and characterized to have the vdW nature with MP2/6-311G(d), except for those in 10 a-12 a, where the ethylene moieties in 1 a are replaced by benzene moieties. The character in 10 a-12 a is predicted to have the typical-HB (hydrogen bond) nature without covalency, although that in 10 a and 11 a seems close to the border area between the two. Indeed, the twisted structures were predicted for 1 a-4 a with MP2/6-311G(d), but the observed non-twisted structures of 1 a-3 a were better reproduced with MP2/6-311G(3d). The typical-HB nature without covalency was additionally predicted for the interactions between ethylene and benzene moieties in 9 a with MP2/6-311G(3d), maybe due to somewhat shorter C Á Á Á C distances predicted for the interactions in question. The interaction in TS is also discussed exemplified by 10 a (C 2v ).

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Section: Introductionmentioning

confidence: 99%

Intramolecular π–π Interactions in Diethanodihydronaphthalene and Derivatives: Dynamic and Static Behavior of the Interactions Elucidated by QTAIM Dual Functional Analysis

2016

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“…Fig. 11 shows the asymmetric unit of CSD entry YOKJOX (Lin et al, 1995), which contains two enantiomers, but the stereochemistry assigned by Open Babel is diastereomeric. ChiChi does recognize these structures as enantiomers, as does Mercury.…”

Section: Comparison To Other Methodsmentioning

confidence: 99%

Searching for stereoisomerism in crystallographic databases: algorithm, analysis and chiral curiosities

Grothe¹,

Meekes²,

Gelder³

2017

Acta Crystallogr Sect B

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The automated identification of chiral centres in molecular residues is a non-trivial task. Current tools that allow the user to analyze crystallographic data entries do not identify chiral centres in some of the more complex ring structures, or lack the possibility to determine and compare the chirality of multiple structures. This article presents an approach to identify asymmetric C atoms, which is based on the atomic walk count algorithm presented by Rücker & Rücker [(1993), J. Chem. Inf. Comput. Sci. 33, 683-695]. The algorithm, which we implemented in a computer program named ChiChi, is able to compare isomeric residues based on the chiral centres that were identified. This allows for discrimination between enantiomers, diastereomers and constitutional isomers that are present in crystallographic databases. ChiChi was used to process 254 354 organic entries from the Cambridge Structural Database (CSD). A thorough analysis of stereoisomerism in the CSD is presented accompanied by a collection of chiral curiosities that illustrate the strength and versatility of this approach.

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“…Attack of an electrophile to a molecule having two isolated double bonds in spatial proximity usually leads to the transannular bridge formation in either cross (Ntype) or parallel (U-type) manner or both [6][7][8][9]. Experimental results on this type of reaction have been confusing.…”

Section: Introductionmentioning

confidence: 93%

DFT study on the electrophilic transannular addition reaction of bromine to tetracyclo[7.2.1.04,11.06,10]dodeca-2,7-diene

Abbasoğlu

Aşamaz

Магеррамов

et al. 2010

Journal of Molecular Structure: THEOCHEM

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Synthesis, reactions and thermal properties of endo-5,12: endo-6,11-dietheno-5,5a,6,11,11a,12-hexahydronaphthacene

Cited by 31 publications

References 43 publications

Intramolecular π–π Interactions in Diethanodihydronaphthalene and Derivatives: Dynamic and Static Behavior of the Interactions Elucidated by QTAIM Dual Functional Analysis

Intramolecular π–π Interactions in Diethanodihydronaphthalene and Derivatives: Dynamic and Static Behavior of the Interactions Elucidated by QTAIM Dual Functional Analysis

Searching for stereoisomerism in crystallographic databases: algorithm, analysis and chiral curiosities

DFT study on the electrophilic transannular addition reaction of bromine to tetracyclo[7.2.1.04,11.06,10]dodeca-2,7-diene

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