Halogen Bonding in Hypervalent Iodine Compounds

2016 ◽  
pp. 289-309 ◽  
Author(s):  
Luca Catalano ◽  
Gabriella Cavallo ◽  
Pierangelo Metrangolo ◽  
Giuseppe Resnati ◽  
Giancarlo Terraneo
Keyword(s):  
Halogen Bonding ◽  
Hypervalent Iodine ◽  
Iodine Compounds

scholarly journals A Continuum from Halogen Bonds to Covalent Bonds: Where Do λ3 Iodanes Fit?

Inorganics ◽  
2019 ◽  
Vol 7 (4) ◽  
pp. 47 ◽  
Author(s):  
Seth Yannacone ◽  
Vytor Oliveira ◽  
Niraj Verma ◽  
Elfi Kraka
Keyword(s):  
Density Functional ◽  
Chemical Properties ◽  
Halogen Bonding ◽  
Covalent Bonding ◽  
Basis Set ◽  
Smooth Transition ◽  
Hypervalent Iodine ◽  
Covalent Bonds ◽  
Iodine Compounds ◽  
Hypervalent Bonds

The intrinsic bonding nature of λ 3 -iodanes was investigated to determine where its hypervalent bonds fit along the spectrum between halogen bonding and covalent bonding. Density functional theory with an augmented Dunning valence triple zeta basis set ( ω B97X-D/aug-cc-pVTZ) coupled with vibrational spectroscopy was utilized to study a diverse set of 34 hypervalent iodine compounds. This level of theory was rationalized by comparing computational and experimental data for a small set of closely-related and well-studied iodine molecules and by a comparison with CCSD(T)/aug-cc-pVTZ results for a subset of the investigated iodine compounds. Axial bonds in λ 3 -iodanes fit between the three-center four-electron bond, as observed for the trihalide species IF 2 − and the covalent FI molecule. The equatorial bonds in λ 3 -iodanes are of a covalent nature. We explored how the equatorial ligand and axial substituents affect the chemical properties of λ 3 -iodanes by analyzing natural bond orbital charges, local vibrational modes, the covalent/electrostatic character, and the three-center four-electron bonding character. In summary, our results show for the first time that there is a smooth transition between halogen bonding → 3c–4e bonding in trihalides → 3c–4e bonding in hypervalent iodine compounds → covalent bonding, opening a manifold of new avenues for the design of hypervalent iodine compounds with specific properties.

scholarly journals Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild Conditions

Molecules ◽  
2021 ◽  
Vol 26 (7) ◽  
pp. 1897
Author(s):  
Hideyasu China ◽  
Nami Kageyama ◽  
Hotaka Yatabe ◽  
Naoko Takenaga ◽  
Toshifumi Dohi
Keyword(s):  
Aqueous Solution ◽  
Room Temperature ◽  
Practical Method ◽  
Hypervalent Iodine ◽  
Mild Conditions ◽  
Sequential Procedures ◽  
Iodine Compounds ◽  
Practical Synthesis ◽  
Iodosobenzoic Acid ◽  
Lower Temperature

We report a convenient and practical method for the preparation of nonexplosive cyclic hypervalent iodine(III) oxidants as efficient organocatalysts and reagents for various reactions using Oxone® in aqueous solution under mild conditions at room temperature. The thus obtained 2-iodosobenzoic acids (IBAs) could be used as precursors of other cyclic organoiodine(III) derivatives by the solvolytic derivatization of the hydroxy group under mild conditions of 80 °C or lower temperature. These sequential procedures are highly reliable to selectively afford cyclic hypervalent iodine compounds in excellent yields without contamination by hazardous pentavalent iodine(III) compound.

The IX (X=O,N,C) Double Bond in Hypervalent Iodine Compounds: Is it Real?

2014 ◽  
Vol 53 (36) ◽  
pp. 9617-9621 ◽  
Author(s):  
Alexander S. Ivanov ◽  
Ivan A. Popov ◽  
Alexander I. Boldyrev ◽  
Viktor V. Zhdankin
Keyword(s):  
Double Bond ◽  
Hypervalent Iodine ◽  
Iodine Compounds

A novel method for the synthesis of 4′-thiopyrimidine nucleosides using hypervalent iodine compounds

2003 ◽  
Vol 1 (21) ◽  
pp. 3692-3697 ◽  
Author(s):  
Naozumi Nishizono ◽  
Ryosuke Baba ◽  
Chika Nakamura ◽  
Kazuaki Oda ◽  
Minoru Machida
Keyword(s):  
Hypervalent Iodine ◽  
Iodine Compounds ◽  
Novel Method

Electrochemical reduction of some hypervalent iodine compounds

1991 ◽  
Vol 36 (9) ◽  
pp. 1391-1395 ◽  
Author(s):  
Georgios Kokkinidis ◽  
Evangelia Hatzigrigoriou ◽  
Dimitra Sazou ◽  
Anastasios Varvoglis
Keyword(s):  
Electrochemical Reduction ◽  
Hypervalent Iodine ◽  
Iodine Compounds
Sign in / Sign up

Export Citation Format

Share Document