The halogen bond between ethene and a simple perfluoroiodoalkane: C2H4⋯ICF3 identified by broadband rotational spectroscopy

Stephens, Susanna L.; Mizukami, Wataru; Tew, David P.; Walker, Nicholas R.; Legon, A. C.

doi:10.1016/j.jms.2012.06.002

Cited by 19 publications

(19 citation statements)

References 26 publications

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“… 24 More recently, this body of work was expanded by the same group to include and compare the gas-phase rotational spectra of new molecular pairs such as ClI···Y 24 , 67 , 262 , 273 , 333 − 341 and CF 3 I···Y. 188 , 189 , 342 − 345 …”

Section: Nature Of the Halogen Bondmentioning

confidence: 99%

“…When the XB acceptor is an isolated π-system, the axis of the R–X covalent bond (R = halogen, 24 , 187 carbon; 188 , 189 X = Cl, Br, I) lies, in the equilibrium geometry, approximately along the symmetry axis of the π-bonding orbital of the XB acceptor ( Figure 15 ). When two conjugated and equivalent π bonds are present on the electron donor system, such as in 1,3-butadiene, R–X lies perpendicular to the plane containing the four carbon atoms of the double bonds and is localized at one π-bonding orbital site with no evidence of tunneling.…”

Section: Introductionmentioning

confidence: 99%

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The Halogen Bond

et al. 2016

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The halogen bond occurs when there is evidence of a net attractive interaction between an electrophilic region associated with a halogen atom in a molecular entity and a nucleophilic region in another, or the same, molecular entity. In this fairly extensive review, after a brief history of the interaction, we will provide the reader with a snapshot of where the research on the halogen bond is now, and, perhaps, where it is going. The specific advantages brought up by a design based on the use of the halogen bond will be demonstrated in quite different fields spanning from material sciences to biomolecular recognition and drug design.

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Section: Nature Of the Halogen Bondmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

The Halogen Bond

et al. 2016

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“…The obtained adducts were characterized in the solid state by single-crystal (XRD) and powder X-ray diffraction, FTIR and solid-state 13 C CP/MAS NMR spectroscopies, and also by thermogravimetric analysis (TG/DTG) (see Supplementary Methods).…”

Section: Solution and Mechanochemical Routes To Isocyanide Adductsmentioning

confidence: 99%

“…The latter contact is 5% longer than ∑BvdW and it is very close to the sum of Rowland vdW radii 28 (∑RvdW). Based on these angular parameters (∠(C-I•••C) 176.29 (13)…”

Section: Solution and Mechanochemical Routes To Isocyanide Adductsmentioning

confidence: 99%

“…XB acceptor centers conventionally include electronegative hetero-atoms bearing lone pair(s) with many elements, such as halogens 8 , chalcogens 9 , pnictogens 10 etc., electrondonating π-systems, and even electron-donating positively charged metal centers 11,12 . Carbon-the structural core of all organic matter, the element that gives the highest diversity of compounds, their forms, and covalent bonds-is involved in noncovalent interactions as XB acceptor mostly as part of a πsystem (e.g., double-bonded 13 , triple-bonded 14 , or aromatic systems 15 ). The solid-state interaction involving the carbon lone pair (lp) and halogen atom has been previously observed in only one case, namely in the adduct (IAd)•IPFB formed upon the interplay of iodopentafluorobenzene (IPFB) and N-heterocyclic carbene (IAd) 16 .…”

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confidence: 99%

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The halogen bond with isocyano carbon reduces isocyanide odor

et al. 2020

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Predominantly, carbon atoms of various species function as acceptors of noncovalent interactions when they are part of a π-system. Here, we report on the discovery of a halogen bond involving the isocyano carbon lone pair. The co-crystallization or mechanochemical liquid-assisted grinding of model mesityl isocyanide with four iodoperfluorobenezenes leads to a series of halogen-bonded adducts with isocyanides. The obtained adducts were characterized by single-crystal and powder X-ray diffraction, solid-state IR and 13 C NMR spectroscopies, and also by thermogravimetric analysis. The formation of the halogen bond with the isocyano group leads to a strong reduction of the isocyanide odor (3-to 46-fold gas phase concentration decrease). This manipulation makes isocyanides more suitable for laboratory storage and usage while preserving their reactivity, which is found to be similar between the adducts and the parent isocyanide in some common transformations, such as ligation to metal centers and the multi-component Ugi reaction.

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Halogen Bond‐Involving Supramolecular Assembly Utilizing Carbon as a Nucleophilic Partner of I⋅⋅⋅C Non‐covalent Interaction

Smirnov

Mikherdov

Rozhkov

et al. 2023

Chemistry An Asian Journal

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Co-crystallization of 180°-orienting σ-hole-accepting tectons, namely, 1,4-diisocyanobenzene (1) and 1,4diisocyanotetramethylbenzene (2), with such homoditopic halogen bond donors as 1,4-diiodotetrafluorobenzene (1,4-FIB) and 4,4'-diiodoperfluorobiphenyl (4,4'-FIBP) afforded cocrystals 1 • 1,4-FIB, 1 • 4,4'-FIBP, and 2 • 1,4-FIB. Their solid-state structures exhibit 1D-supramolecular arrangements, which are based on poorly explored I•••C halogen bonding; this study is the first in which the supramolecular assembly utilizing halogen bonding with a terminal C atom was performed. The use of the potentially tetrafunctional σ-hole accepting tetraiodoethylene (TIE) leads to supramolecular architecture of a higher dimension, 3D-framework, observed in the structure of 1 • TIE. DFT calculations, used to characterize the halogen bonding situation, revealed that the I•••C noncovalent interactions are moderately strong, ranging from À 4.07 in 1 • TIE to À 5.45 kcal/mol in 2 • 1,4-FIB. The NBO analysis disclosed that LP(C)!σ* charge transfer effects are relevant in all co-crystals.

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The halogen bond between ethene and a simple perfluoroiodoalkane: C2H4⋯ICF3 identified by broadband rotational spectroscopy

Cited by 19 publications

References 26 publications

The Halogen Bond

The Halogen Bond

The halogen bond with isocyano carbon reduces isocyanide odor

Halogen Bond‐Involving Supramolecular Assembly Utilizing Carbon as a Nucleophilic Partner of I⋅⋅⋅C Non‐covalent Interaction

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