Impact and importance of electrostatic potential calculations for predicting structural patterns of hydrogen and halogen bonding

Perera, Manomi D.; Desper, John; Sinha, Abhijeet S.; Aakeröy, Christer B.

doi:10.1039/c6ce02089e

Cited by 63 publications

(56 citation statements)

References 39 publications

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“…Due to the extensive applications of non‐covalent interactions, the competition, cooperation and coexistence among them have generated extensive research. It is especially important to study the competition between hydrogen bonds and halogen bonds, as these two types of interactions are directional and relatively strong, and their importance in crystal engineering originates from their shared dependence upon long‐range electrostatic forces] . By combining interactions that do not compete for the same molecular binding sites it is, in principle, possible to avoid or at least minimize “synthon cross‐over” thereby producing architectures of considerable complexity .…”

Section: Introductionmentioning

confidence: 99%

“…It is especially important to study the competition between hydrogen bonds and halogen bonds, as these two types of interactions are directional and relatively strong, and their importance in crystal engineering originates from their shared dependence upon long-range electrostatic forces]. [26][27][28][29][30] By combining interactions that do not compete for the same molecular binding sites it is, in principle, possible to avoid or at least minimize "synthon cross-over" [31] thereby producing architectures of considerable complexity. [32][33][34][35] Moreover, it is well known that hydrogen bonding plays an important role in the human body; for example, human DNA structure is highly dependent upon hydrogen bonds.…”

Section: Introductionmentioning

confidence: 99%

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Comparison between Hydrogen and Halogen Bonds in Complexes of 6‐OX‐Fulvene with Pnicogen and Chalcogen Electron Donors

Hou

Scheiner

2019

ChemPhysChem

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Quantum chemical calculations are applied to complexes of 6‐OX‐fulvene (X=H, Cl, Br, I) with ZH3/H2Y (Z=N, P, As, Sb; Y=O, S, Se, Te) to study the competition between the hydrogen bond and the halogen bond. The H‐bond weakens as the base atom grows in size and the associated negative electrostatic potential on the Lewis base atom diminishes. The pattern for the halogen bonds is more complicated. In most cases, the halogen bond is stronger for the heavier halogen atom, and pnicogen electron donors are more strongly bound than chalcogen. Halogen bonds to chalcogen atoms strengthen in the order O

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Comparison between Hydrogen and Halogen Bonds in Complexes of 6‐OX‐Fulvene with Pnicogen and Chalcogen Electron Donors

Hou

Scheiner

2019

ChemPhysChem

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“…Chelation of the Re centre also inuences the spatial arrangement of the two C-I groups on the bistriazole unit improving preorganisation of the rotaxane for binding. As part of a continuing programme of study of the competition between intermolecular interactions in supramolecular synthesis of crystals, [66][67][68][69] Aakeröy and co-workers have designed a series of 1-(pyridylmethyl)-2,2 0 -biimidazoles, which contain three different sites capable of being hydrogen bond or halogen bond acceptors (Scheme 1). Co-crystallisation with a series of ditopic hydrogen bond donors and halogen bond donors allowed selectivity patterns for intermolecular interaction formation to be examined (DOI: 10.1039/c7fd00080d).…”

Section: Applicationsmentioning

confidence: 99%

Halogen bonding, chalcogen bonding, pnictogen bonding, tetrel bonding: origins, current status and discussion

2017

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The role of the closing lecture in a Faraday Discussion is to summarise the contributions made to the Discussion over the course of the meeting and in so doing capture the main themes that have arisen. This article is based upon my Closing Remarks Lecture at the 203 Faraday Discussion meeting on Halogen Bonding in Supramolecular and Solid State Chemistry, held in Ottawa, Canada, on 10-12 July, 2017. The Discussion included papers on fundamentals and applications of halogen bonding in the solid state and solution phase. Analogous interactions involving main group elements outside group 17 were also examined. In the closing lecture and in this article these contributions have been grouped into the four themes: (a) fundamentals, (b) beyond the halogen bond, (c) characterisation, and (d) applications. The lecture and paper also include a short reflection on past work that has a bearing on the Discussion.

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“…Access to calculated molecular electrostatic potential surface maps on molecules with multiple acceptors and donors provides valuable information for estimating the most probable binding preferences for a target molecule in co-crystallization experiments (Perera et al, 2016;Aakerö y et al, 2013Aakerö y et al, , 2015. Both the mimic and erlotinib contain the same type of potential hydrogen-bond acceptors and both are equipped with an ethynyl group and an N-H moiety which are capable of acting as hydrogen-bond donors (Engle et al, 2011;Aakerö y et al, 2017).…”

Section: Molecular Electrostatic Potential Calculations Of Em and Erlmentioning

confidence: 99%

Using structural mimics for accessing and exploring structural landscapes of poorly soluble molecular solids

Perera

Sinha

Aakeröy

2018

Acta Crystallogr Sect B

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The importance of using structural mimics for mapping out the structural landscape of a poorly soluble active pharmaceutical ingredient was investigated using erlotinib as an example. A mimic was synthesized by preserving the main molecular functionalities responsible for creating the most probable structural arrangements in the solid state. Calculated molecular electrostatic potentials on both erlotinib and the mimic showed very comparable values indicating that the latter would be able to form hydrogen bonds of similar probability and strength as those of erlotinib. In order to establish the binding preference in cocrystallization experiments, the mimic molecule was co-crystallized with US Food and Drug Administration approved dicarboxylic acids. The crystal structures of the mimic and of four co-crystals thereof were obtained. The mimic forms hydrogen bonds in a way that closely resembles those found in the crystal structure of erlotinib. The four co-crystals display self-consistent hydrogen-bond interactions. Thermal and solubility data for the co-crystals demonstrate that by making systematic and controllable changes to the solid forms of the mimic, it is also possible to alter the behaviour and properties of the new solid forms. The use of a suitable structural mimic can allow for a systematic structural examination of a compound that is otherwise not amenable to such investigations by facilitating the elucidation and mapping out of a closely related structural landscape.

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Impact and importance of electrostatic potential calculations for predicting structural patterns of hydrogen and halogen bonding

Abstract: Calculated molecular electrostatic potential difference (ΔMEP) of acceptor atoms in a multi component system will lead to different supramolecular architectures.

Cited by 63 publications

References 39 publications

Comparison between Hydrogen and Halogen Bonds in Complexes of 6‐OX‐Fulvene with Pnicogen and Chalcogen Electron Donors

Comparison between Hydrogen and Halogen Bonds in Complexes of 6‐OX‐Fulvene with Pnicogen and Chalcogen Electron Donors

Halogen bonding, chalcogen bonding, pnictogen bonding, tetrel bonding: origins, current status and discussion

Using structural mimics for accessing and exploring structural landscapes of poorly soluble molecular solids

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