Marvellous molecular shapes

Álvarez, Santiago

doi:10.1016/j.crci.2019.03.005

Cited by 3 publications

(6 citation statements)

References 43 publications

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“…Two attractive examples of the sophisticated supramolecular architectures that can be assembled around a single TMA cation, highlighted earlier by one of us, 9 are the TMA auride 10 and the isostructural bromide, 11 whose polyhedral environment of hydrogen atoms is shown in Figure 1b. The anion is linked by 24 hydrogen atoms forming an asymmetric rhombicuboctahedron (Figure 2).…”

Section: ■ Introductionmentioning

confidence: 93%

“…For simplicity, however, we will consistently use the κ 1 C notation that will be shown to be in better agreement with the nature of the interaction. In many instances, an anion is linked to one H atom of two (8) or three (9) different methyl groups of the same ammonium cation, a situation that is indicated by a numeric prefix and the atomic symbols of the linked atoms, e.g., 3κ 1 H,H′,H″, which will be shortened throughout this paper to 3κ 1 H, given the equivalence of the three H atoms. Examples of the binding topologies that can be found in several simple n-methylammonium salts are presented in Table 1.…”

Section: ■ Introductionmentioning

confidence: 99%

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Tetramethylammonium Cation: Directionality and Covalency in Its Interactions with Halide Ions

2022

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The degree of interpenetration of the van der Waals crusts of two atoms, represented by a penetration index, is defined to better quantify the meaning of the nonbonding contact distances between two atoms, which should allow us to compare different atom pairs on the same footing. The structural trends of the intermolecular contacts between the tetramethylammonium cation (TMA) and halogen atoms are reviewed, and a computational study of model X···TMA ion pairs (X = F, Cl, Br, I, Au) is presented. The results disclose two energy minima, in each of which the anion simultaneously interacts with three hydrogen atoms. The bonding mechanisms in the two cases are discussed based on the results of the tools of the trade that provide a consistent picture in which a distribution of charges significantly varies not only around each different atom but is also strongly dependent on the distance to the central N atom. This behavior, together with some non-negligible covalent character of the interionic interaction, is not predicted from a single-molecular electrostatic potential map of the TMA cation.

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Section: ■ Introductionmentioning

confidence: 93%

Section: ■ Introductionmentioning

confidence: 99%

Tetramethylammonium Cation: Directionality and Covalency in Its Interactions with Halide Ions

2022

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“…wards-pointing lone pairs (l). Moreover, we have seen that the electrons not involved in peripheral bonding can be either used in σor π-bonding (c = σ + π), and the distribution of the valence electrons in the cluster is expressed by eqn (1).…”

Section: Paper Dalton Transactionsmentioning

confidence: 99%

“…23d), 118 whose structure has been commented upon in more detail recently. 1 A few other structures that appear in that region of the shape maps…”

Section: Dalton Transactions Papermentioning

confidence: 99%

“…Chemists are often deceived by the representations of threedimensional molecules in a plane, 1 yet, the way in which planar molecules can evolve away from Flatland and into the 3D world is a thought experiment from which much can be learnt about stereochemistry, chemical bonding, isomerism, and even chemical reaction paths. We have earlier shown how, in the realm of organic chemistry, the non planarity of six member rings in their chair conformation is nicely described by the minimal distortion path from the planar hexagon to the Platonic octahedron, whereas the rings with a boat conformation are found along the path between the hexagon and the regular trigonal prism.…”

Section: Introductionmentioning

confidence: 99%

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From polygons to polyhedra through intermediate structures. A shape measures study of six-atom inorganic rings and clusters

Álvarez

2021

Dalton Trans.

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Effect of [n]-Helicene Length on Crystal Packing

Schmidt,

Wolpert,

Sparrow

et al. 2023

Crystal Growth & Design

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Chiral π-conjugated organic molecules hold potential for emerging technologies as they are capable of introducing novel functionalities into electronic devices owing to their strong chiroptical properties. However, capitalizing on chiral molecules for electronic devices is reliant on their molecular packinga factor that impacts their charge-transport properties. The solid-state behavior of molecules is sensitive to subtle differences in molecular interactions, chirality, and shape, but these relationships are not fully understood. Here, we employ crystal structure prediction (CSP) as a tool to probe the lattice-energy landscape for a family of chiral organic molecules: [n]helicenes, where n ranges from 3 to 12. Our results show excellent agreement between the CSP landscapes and experimentally reported structures. By analyzing the packing motifs within the polymorph landscapes, we begin to develop an understanding of how helicene length affects the shape and π–π stacking interactions seen in the polymorphs. Furthermore, we propose how helicene length can be used as a tool to design new functional organic electronics.

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Marvellous molecular shapes

Cited by 3 publications

References 43 publications

Tetramethylammonium Cation: Directionality and Covalency in Its Interactions with Halide Ions

Tetramethylammonium Cation: Directionality and Covalency in Its Interactions with Halide Ions

From polygons to polyhedra through intermediate structures. A shape measures study of six-atom inorganic rings and clusters

Effect of [n]-Helicene Length on Crystal Packing

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