Supramolecular Self-assembly of Transition Metal Carbonyl Molecules Through M–CO(Lone Pair)…π(Arene) Interactions

Zukerman-Schpector, Júlio; Haiduc, Ionel; Tiekink, Edward R. T.

doi:10.1016/b978-0-12-396970-5.00002-5

Cited by 31 publications

(6 citation statements)

References 149 publications

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“…4 The metal carbonyl interaction with p-aryl groups has recently been identified as a factor in the stabilization of the crystal packing in compounds containing metal carbonyl units. 15,16 A third structural motif can be identified in Fig. 4.…”

mentioning

confidence: 98%

Reshaping molecules through cocrystallization. Comparison of the structures of Hg{Co(CO)4}2 and Hg{Co(CO)4}2·C60·toluene

et al. 2013

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mentioning

confidence: 98%

Reshaping molecules through cocrystallization. Comparison of the structures of Hg{Co(CO)4}2 and Hg{Co(CO)4}2·C60·toluene

et al. 2013

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“…Lone pair−π interactions are stabilizing noncovalent interactions between an atom with lone pairs and a π-system. − One of the most common types involves carbonyl oxygens interacting with aromatic π-surfaces (Figure ). − Carbonyl–aromatic (CO···Ar) interactions are key contributors to the selectivity, conformation, and activity of small molecules, nucleosides, and peptides. , Despite the importance of CO···Ar interactions, key fundamental questions regarding their ability to stabilize transition states (TSs) and the relative contributions of the electrostatic and orbital delocalization components to the interaction energy remain.…”

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confidence: 99%

Analysis of the Orbital and Electrostatic Contributions to the Lone Pair–Aromatic Interaction Using Molecular Rotors

Vik

Madukwe

et al. 2021

Org. Lett.

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The attractive interaction between carbonyl oxygens and the π-face of aromatic surfaces was studied using N-phenylimide molecular rotors. The CO•••Ar interactions could stabilize the transition states but were half the strength of comparable CO•••C O interactions. The CO•••Ar interaction had a significant electrostatic component but only a small orbital delocalization component. Letter pubs.acs.org/OrgLett

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“…Each crystal also features C=O … π interactions. This type of interaction is known to be significant in stabilising the molecular packing of both heavy-element and organic molecules and have been shown to sustain recognisable aggregation patterns [64][65][66][67][68]. It is noted that while attractive, such C=O … π interactions contribute relative small energies of stabilisation to crystals in which they are formed, i.e.…”

Section: Molecular Packingmentioning

confidence: 99%

“…It is noted that while attractive, such C=O … π interactions contribute relative small energies of stabilisation to crystals in which they are formed, i.e. probably < 10 kJ mol -1 , based on DFT calculations [64][65][66][67][68][69]. The persistence of these interactions in the molecular packing of 1-5 is of interest.…”

Section: Molecular Packingmentioning

confidence: 99%

On the influence of small chemical changes upon the supramolecular association in substituted 2-(phenoxy)-1,4-naphthoquinones

Tonin

Garden

Jotani³

et al. 2018

Zeitschrift Für Kristallographie - Crystalline Materials

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X-ray crystallography reveals the common feature of the title compounds is a 1,4-naphthoquinone ring system with a substituted phenoxy residue adjacent to an oxo-group to give 1 (H), 2 (3-Br), 3 (3-CF3), 4 (4-CN) and 5 (4-NO2). To a first approximation the fused ring system along with the two oxo substituents is planar with the major difference between the molecules relating to the relative orientations of the pendant phenoxy residues: dihedral angles range from 56.56(4)° (3) to 87.52(10)° (2). The presence of intermolecular C–H···O interactions is the common feature of the supramolecular association in the crystals of 1–5. In each of 1 and 5, these extend in three-dimensions but, only to supramolecular dimers in 4, chains in 2 and layers in 3. Each crystal also features C=O···π interactions, pointing to the importance of these points of contact in this series di-oxocompounds. In 2, these, along with C–Br···π interactions lead to a three-dimensional architecture. For 3, the C=O···π and π···π interactions occur within the layers which stack without directional interactions between them. In 4, C–H···O and C=O···π interactions combine to give a supramolecular layer, which also stack without directional interactions in the inter-layer region. Further analysis of the molecular packing was conducted by a Hirshfeld surface analysis (HSA). This points to the significant role of H···H, C···H/H···C and O···H/H···O contacts in the packing of 1. Notably different roles for these contacts are found in the other crystals correlating with the participation of the respective substituents in the molecular packing. The HSA suggests the association between layers in 3 (weak F···F and H···F interactions) and 4 (weak H···N interactions) is contributed by the phenoxy-substituents.

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Supramolecular Self-assembly of Transition Metal Carbonyl Molecules Through M–CO(Lone Pair)…π(Arene) Interactions

Cited by 31 publications

References 149 publications

Reshaping molecules through cocrystallization. Comparison of the structures of Hg{Co(CO)4}2 and Hg{Co(CO)4}2·C60·toluene

Reshaping molecules through cocrystallization. Comparison of the structures of Hg{Co(CO)4}2 and Hg{Co(CO)4}2·C60·toluene

Analysis of the Orbital and Electrostatic Contributions to the Lone Pair–Aromatic Interaction Using Molecular Rotors

On the influence of small chemical changes upon the supramolecular association in substituted 2-(phenoxy)-1,4-naphthoquinones

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