Aryl-platform-based tetrapodal 2-iodo-imidazolium as an excellent halogen bond receptor in aqueous medium

Chakraborty, Sourav; Maji, Siddhartha; Ghosh, Rajib; Jana, Rajkumar; Datta, Ayan; Ghosh, Pradyut

doi:10.1039/c8cc09937e

Cited by 23 publications

(11 citation statements)

References 44 publications

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“…Moreover, in connection with the latter idea of the presence of multiple noncovalent bonds there is indeed growing interest concerning the clustering of molecules, for instance (PH 2 F) n , (PH 2 Cl) n , NH 3 , PH 3 , and PFH 2 and HF, FCl, − wherein such multiple bonds are integral. It has long been recognized that the formation of a HB polarizes each participant and affects their ability to engage in a second such bond.…”

Section: Introductionmentioning

confidence: 99%

How Many Pnicogen Bonds can be Formed to a Central Atom Simultaneously?

et al. 2020

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A central ZF 3 molecule (Z = P, As, Sb, Bi) is allowed to interact with a number of nucleophiles exemplified by NCH, NH 3 , and NC – anion. The Z···N pnicogen bond (ZB) to a single base grows stronger for heavier Z atom: P < A < Sb < Bi and follows the NCH < NH 3 < NC – order for the three bases. The maximum number of ZBs depends on both the nature of the base and pnicogen atom. PF 3 and AsF 3 can pnicogen bond with only a single CN – ; SbF 3 and BiF 3 can interact with two anions but only weakly. The weak NCH nucleophile can engage in a maximum of two ZBs, while three ZBs occur for NH 3 . The latter NH 3 maximum can be extended to four ZBs but only for BiF 3 . The fourth ZB is somewhat longer and weaker than the others, and the entire (H 3 N) 4 ···BiF 3 complex relies partially on secondary interactions for its stability.

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Section: Introductionmentioning

confidence: 99%

How Many Pnicogen Bonds can be Formed to a Central Atom Simultaneously?

et al. 2020

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“…By mixing the imidazolium hexafluorophosphates ( 2 , 3 ) with tetrabutylammonium salts (Bu 4 N + X − ) in MeCN, the desired compounds could be selectively precipitated through the addition of Et 2 O, owing to the high solubility of Bu 4 N + PF 6 − in MeCN / Et 2 O mixtures. Similar approaches were recently employed in the isolation of halide salts of metal complexes [26] and their ligand precursors, [27] in studies regarding halogen bonding, [28–30] as well as in anion metathesis of an oxime antidote [31] …”

Section: Introductionmentioning

confidence: 94%

N,N‐Dimethoxyimidazolium Derivatives as Ion Pair Constituents of Energetic Redox Couples: Model Studies by Thermal Analysis and Crystallography

Fliri

Gelbrich

Griesser

et al. 2021

Zeitschrift anorg allge chemie

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By utilizing an expedient anion exchange protocol and starting with an improved synthesis of 2‐azido‐1,3‐dimethoxyimidazolium hexafluorophosphate, a series of six metathetical salts, including the energetic nitrate and perchlorate as well as the halides, was prepared. We focused on the crystallographic and thermal characterization of these compounds, representing intrinsically reactive hybrid organic / inorganic salts, and conducted a small comparative study with the related 2‐methyl‐1,3‐dimethoxyimidazolium salts. The latter compounds were expected to thermally disintegrate less sluggishly since the covalent azido‐group as intrinsic blasting initiator is missing. Both 2‐azido‐ and 2‐methylimidazolium nitrate exhibit a very sharp thermal onset of complete disintegration. In contrast, the respective perchlorates display a continuous thermogravimetric weight loss over a broad temperature range. Additionally, X‐ray single crystal structure determinations were performed for eight of the new compounds as well as for two 2‐azido‐1,3‐dimethoxyimidazolium salts with a mixed anion composition. Phase purity was also checked for five of the congeners using powder X‐ray diffraction (Pawley fitting). Notably, in the 2‐azido‐imidazolium cation, the intra‐ring bonds of the N1−C2 type were found to be significantly shorter than N1−C4 type bonds, and a characteristic asymmetry between the two N1−C2−N(azido) bond angles was observed. The experimental cation geometry was reproduced by DFT calculations on selected compounds.

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“…Interrogation of the CSD for 2-haloimidazolium salts with distorted imidazolium rings identified three datasets for two crystal structures with residual electron density typical of the structures presented herein. 36,37 The residual density in both structures was not modelled in their respective publications, and the authors of the former paper reported the data collection of crystals from multiple batches, and finalised the structure with one isotropic carbon atom to minimise the influence of the residual electron density on the 2-iodoimidazolium ring. 36 Our re-refinement of the data indicates the disorder of the 2-iodoimidazolium group across two positions with a very minor secondary component where the iodine contribution is visible in the difference map, but the relatively smaller carbon and nitrogen atoms are not apparent (or readily modelled without significant restraints and constraints).…”

Section: Disorder In Previous Halogen Bonding Studiesmentioning

confidence: 99%

Disorder in 2-bromoimidazolium hexafluorophosphate salts: the role of halogen bonds

Wolfenden

Taylor

et al. 2023

CrystEngComm

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Aryl-platform-based tetrapodal 2-iodo-imidazolium as an excellent halogen bond receptor in aqueous medium

Abstract: The graphic shows a halogen bonding interaction between a tetrapodal platform attached to a 2-iodo-imidazole unit and bromide in water.

Cited by 23 publications

References 44 publications

How Many Pnicogen Bonds can be Formed to a Central Atom Simultaneously?

How Many Pnicogen Bonds can be Formed to a Central Atom Simultaneously?

N,N‐Dimethoxyimidazolium Derivatives as Ion Pair Constituents of Energetic Redox Couples: Model Studies by Thermal Analysis and Crystallography

Disorder in 2-bromoimidazolium hexafluorophosphate salts: the role of halogen bonds

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