Periodate anions as a halogen bond donor: formation of anion⋯anion dimers and other adducts

Calabrese, Miriam; Pizzi, Andrea; Daolio, Andrea; Frontera, Antonio; Resnati, Giuseppe

doi:10.1039/d2cc03191d

Cited by 13 publications

(22 citation statements)

References 28 publications

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“…Taking into account the differences in bond distances involving iodine (well below 2.0 Å for single or double I–O bonds), a (4 + 2) pseudo-octahedral ICO 5 geometry can be envisaged (see Figure S2). Similar intermolecular interactions (though significantly longer than those found in our study, that is 3.5 vs 3.0 Å) have been detected in periodate organic salts and discussed in the frame of multivalent halogen bonds . In PIBX and QUIBX, the pyridine and quinoline molecules are linked to the IBX lattice via a I–O···H···N hydrogen bond.…”

Section: Resultssupporting

confidence: 87%

Salt or Cocrystal? Using XRPD to Infer Proton Transfer in Three Adducts of Iodoxybenzoic Acid by Analyzing Iodine–Oxygen Bond Lengths

Vladiskovic

Mantegazza

Razzetti

et al. 2023

Crystal Growth & Design

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2-Iodoxybenzoic acid (IBX) is a versatile oxidant, which has been used for a plethora of reactions through the years. Its explosive properties and low solubility, the major limitations to a more widespread use of this reactant, have led to the search for derivatives, adducts, or mixtures with comparable oxidative properties but better characteristics. In this paper, different adducts of IBX, in particular with pyridine (PIBX), quinoline (QUIBX), and nicotinamide (B3-IBX), have been structurally characterized using state-of-the-art X-ray powder diffraction (XRPD) methods. Their oxidative properties have been tested and compared to those of pristine IBX. While generally structure determination from XRPD does not allow us to investigate the proton position, a strategy was devised based on the investigation of iodine–oxygen exocyclic bond lengths to discriminate between single and double iodine–oxygen bonds. The final aim was to attempt to use XRPD to answer an elusive question: salt or cocrystal?

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Section: Resultssupporting

confidence: 87%

Salt or Cocrystal? Using XRPD to Infer Proton Transfer in Three Adducts of Iodoxybenzoic Acid by Analyzing Iodine–Oxygen Bond Lengths

Vladiskovic

Mantegazza

Razzetti

et al. 2023

Crystal Growth & Design

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“…In this case, this multivalent halogen bond’s Cl···O distance is slightly longer than the ΣR vdw (3.35 Å). Although multivalent halogen bonds in the +7 oxidation state such as in the KUCRAD dimer are not common, the structure-directing role of similar halogen bonds has been recently reported in periodate salts [ 21 ]. The resemblance of chalcogen and halogen bonds in the self-assembled dimers with the matere bonds in HETRUT is remarkable, and further reinforces the fact that such contacts are most likely σ-hole interactions, as further analyzed below.…”

Section: Resultsmentioning

confidence: 99%

Matere Bonds vs. Multivalent Halogen and Chalcogen Bonds: Three Case Studies

Gomila

Frontera

2022

Molecules

Self Cite

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The term matere bond has been recently used to refer to an attractive noncovalent interaction between any element of group 7 acting as an electrophile and any atom (or group of atoms) acting as a nucleophile. The utilization of metals such as σ-hole donors is starting to attract the attention of the scientific community. In this manuscript, a comparison between matere bonds and well-known σ-hole interactions (halogen and chalcogen bonds) is carried out using three X-ray structures, retrieved from the Cambridge structural database (CSD), and density functional theory calculations (DFT). The novelty of this work resides in the utilization of a neutral Re(VII) system as the matere bond donor and multivalent chalcogen and halogen donors. In fact, as far as our knowledge extends, the description of σ-hole interactions in Se(VI) is unprecedented in the literature. The σ-hole interactions in Re(VII), Se(VI) and Cl(VII) electron acceptors are analyzed and compared using several computational tools.

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“…67,68 Pairs of this sort are typically unstable unless they are immersed in a simulated solvent of some sort, or a series of counterions have been added, to disperse the charges and minimize Coulombic repulsions. [69][70][71][72][73][74][75][76][77][78] In some cases, metastable complexes can be identified in the gas phase, but these are higher in energy than the separated monomers. 25,[79][80][81][82][83][84][85] Fully stable minima can be achieved in the gas phase if the two cations are large enough that there is large separation between their centers of like charge.…”

Section: Discussionmentioning

confidence: 99%

Does a halogen bond require positive potential on the acid and negative potential on the base?

Scheiner

2023

Phys. Chem. Chem. Phys.

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Periodate anions as a halogen bond donor: formation of anion⋯anion dimers and other adducts

Abstract: Single crystal X-ray analyses show that iodine in pyridinium periodates acts as halogen bond (HaB) donor forming short and almost linear contacts with neutral and anionic electron donors. A combination...

Cited by 13 publications

References 28 publications

Salt or Cocrystal? Using XRPD to Infer Proton Transfer in Three Adducts of Iodoxybenzoic Acid by Analyzing Iodine–Oxygen Bond Lengths

Salt or Cocrystal? Using XRPD to Infer Proton Transfer in Three Adducts of Iodoxybenzoic Acid by Analyzing Iodine–Oxygen Bond Lengths

Matere Bonds vs. Multivalent Halogen and Chalcogen Bonds: Three Case Studies

Does a halogen bond require positive potential on the acid and negative potential on the base?

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