Intermolecular recognition between hydrocarbon oxygen-donors and perfluorocarbon iodine-acceptors: the shortest O⋯I non-covalent bond

Halogen-Bonded Co-Crystals of Aromatic N-oxides: Polydentate Acceptors for Halogen and Hydrogen Bonds

“…A Cambridge Structural Database (CSD) search for pyridine Noxides functioning as XB acceptors revealed only a handful of structures (see supporting information for more details), while their systematic investigations remain especially scarce [32][33][34]. Previously, monodentate strong N − −I + ···O − −N + XBs (RXB as low as 0.66) of coordinative nature between pyridine N-oxides and N-haloimides were studied both in solution and in the solid-state [35].…”

CX⋅⋅⋅O Halogen Bonding: Interactions of Trifluoromethyl Halides with Dimethyl Ether

“…These interactions, often referred to as halogen bonding, [1,2] not only involve dihalogens of the types X 2 and XY, [3][4][5][6][7] but also appear for a variety of carbon-bound halogen atoms occurring in alkyl and aryl halides. [3][4][5][6] These non-covalent interactions between the carbon-bound halogen atoms and electron donors have been proven to be an essential driving force for crystal engineering and supramolecular self-assembly, [7][8][9][10][11][12][13][14] molecular recognition, [15][16][17][18] and various biochemical processes, [19][20][21][22] and, consequently, have been the subject of a variety of experimental and theoretical studies. [23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38][39] Experimental studies involving CÀhalogen···Y interactions tend to concentrate on Lewis bases Y in which the electron donor atom is nitrogen.…”

“…[23,24,40] That choice is obviously influenced by the fact that the interaction with oxygen-or sulfurcontaining bases are predicted to be much weaker. Although some experimental data on halogen···oxygen complexes can be found in the literature, [3,30] no systematic experimental data on the strength of that interaction are available. This study is a first contribution to fill this gap, by studying the infrared and Raman spectra of complexes of CF 3 X (X= Cl, Br, I) with dimethyl ether, in liquid rare gases, a technique that allows not only the straightforward detection of complex formation, but also allows the determination of complexation enthalpies as a measure of their stabilities.…”

Constructing molecular polygons using halogen bonding and bifurcated N-oxides

“…Heteroaromatic N-oxides have shown to interact effectively as electron donors towards perfluorocarbon iodides. 13 Despite the 30 many similarities between hydrogen bonding and halogen bonding, there are no reports on the deliberate use of bifurcated halogen bonds in combination with N-oxides for directed assembly of supramolecular architectures with predetermined topology and stoichiometries. In principle, such an undertaking 35 should be possible as the halogen bond is mainly electrostatic in nature, and involves an electropositive -hole on a halogen atom and an electron-pair donor.…”