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

2019 ◽  
Vol 55 (10) ◽  
pp. 1506-1509 ◽  
Author(s):  
Sourav Chakraborty ◽  
Siddhartha Maji ◽  
Rajib Ghosh ◽  
Rajkumar Jana ◽  
Ayan Datta ◽  
...  
Keyword(s):  
Aqueous Medium ◽  
Halogen Bond ◽  
Halogen Bonding ◽  
Bonding Interaction

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

scholarly journals Adenine as a Halogen Bond Acceptor: A Combined Experimental and DFT Study

Crystals ◽  
2019 ◽  
Vol 9 (4) ◽  
pp. 224 ◽  
Author(s):  
Yannick Roselló ◽  
Mónica Benito ◽  
Elies Molins ◽  
Miquel Barceló-Oliver ◽  
Antonio Frontera
Keyword(s):  
Density Functional ◽  
Halogen Bond ◽  
Lone Pair ◽  
Halogen Bonding ◽  
Density Functional Theory Calculations ◽  
Functional Theory ◽  
Adenine Ring ◽  
Bonding Interaction ◽  
Donor Ability ◽  
Adenine Derivative

In this work, we report the cocrystallization of N9-ethyladenine with 1,2,4,5-tetrafluoro-3,6-diiodobenzene (TFDIB), a classical XB donor. As far as our knowledge extends, this is the first cocrystal reported to date where an adenine derivative acts as a halogen bond acceptor. In the solid state, each adenine ring forms two centrosymmetric H-bonded dimers: one using N1···HA6–N6 and the other N7···HB6–N6. Therefore, only N3 is available as a halogen bond acceptor that, indeed, establishes an N···I halogen bonding interaction with TFDIB. The H-bonded dimers and halogen bonds have been investigated via DFT (Density Functional Theory) calculations and the Bader’s Quantum Theory of Atoms In Molecules (QTAIM) method at the B3LYP/6-311+G* level of theory. The influence of H-bonding interactions on the lone pair donor ability of N3 has also been analyzed using the molecular electrostatic potential (MEP) surface calculations.

scholarly journals Elimination of Ethene from 1,2-Diiodoethane Induced by N-Heterocyclic Carbene Halogen Bonding

2019 ◽  
Vol 72 (8) ◽  
pp. 614 ◽  
Author(s):  
Tiffany B. Poynder ◽  
Dharmeshkumar P. Savaliya ◽  
Andrew Molino ◽  
David J. D. Wilson ◽  
Jason L. Dutton
Keyword(s):  
Nucleophilic Substitution ◽  
Organic Compounds ◽  
Theoretical Study ◽  
Halogen Bond ◽  
Halogen Bonding ◽  
Alkyl Halides ◽  
Subsequent Investigation ◽  
Bonding Interaction ◽  
Sn2 Pathway

The attempted synthesis of N-heterocyclic carbene (NHC)-stabilised dicarbon (C2) fragments via nucleophilic substitution at 1,2-diiodoethane is reported. Rather than the expected SN2 pathway, clean elimination of ethene and formation of an iodoimidazolium cation was observed. The resistance towards nucleophilic substitution piqued interest, and subsequent investigation determined NHC-halogen bonding as the source. This is in contrast to reactions between NHCs and other alkyl halides, where substitution or elimination pathways are reported. A detailed theoretical study between these cases highlights the importance of iodine as a halogen bond donor compared with other halogens, and shows that NHCs are excellent halogen bond acceptors. This reactivity suggests potential for application of the halogen bonding interaction between NHCs and organic compounds.

Halogen bonding in cadmium(II) MOFs: influence on the structure and on the nitroaldol reaction in aqueous medium

2022 ◽  
Author(s):  
Atash V Gurbanov ◽  
Maxim L. Kuznetsov ◽  
Anirban Karmakar ◽  
Vusala Aliyeva ◽  
Kamran T. Mahmudov ◽  
...  
Keyword(s):  
Aqueous Medium ◽  
Halogen Bond ◽  
Halogen Bonding ◽  
Isophthalic Acid ◽  
Solvothermal Reaction ◽  
Nitroaldol Reaction

A solvothermal reaction of Cd(II) with the dicarboxyl-functionalized arylhydrazone pro-ligands - 5-(2-(2,4,6-trioxotetrahydro-pyrimidin-5(2H)-ylidene)hydrazineyl)isophthalic acid (H5L1) and 5-(2-(2,4-dioxopentan-3-ylidene)hydrazineyl)isophthalic acid (H3L2), or their halogen bond donor centre(s) decorated versions 2,4,6-triiodo-5-(2-(2,4,6-trioxotetrahydropyrimidin-5(2H)-ylidene)hydrazineyl)isophthalic acid (H5L3) and...

Competition between the hydrogen bond and the halogen bond in a [CH3OH–CCl4] complex: a matrix isolation IR spectroscopy and computational study

2020 ◽  
Vol 22 (39) ◽  
pp. 22465-22476
Author(s):  
Dhritabrata Pal ◽  
Sumit Kumar Agrawal ◽  
Amrita Chakraborty ◽  
Shamik Chakraborty
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Ir Spectroscopy ◽  
Computational Study ◽  
Halogen Bond ◽  
Matrix Isolation ◽  
Halogen Bonding ◽  
Bond Interaction ◽  
Bonding Interaction ◽  
Polar Mixtures

Halogen bonding interaction (X-Bond) is prevalent over hydrogen bonding (H-Bond) interaction in [CH3OH–CCl4] mixtures/clusters: consequence in polar/non-polar mixtures and/or corresponding complexes in atmosphere needs to be investigated.

Cyclic networks of halogen-bonding interactions in molecular self-assemblies: a theoretical N—X...NversusC—X...N investigation

2017 ◽  
Vol 73 (2) ◽  
pp. 179-187
Author(s):  
Ruben D. Parra ◽  
Álvaro Castillo
Keyword(s):  
Electron Density ◽  
Self Assembly ◽  
Metal Ion ◽  
Halogen Atom ◽  
Halogen Bond ◽  
Halogen Bonding ◽  
Nbo Analysis ◽  
Binding Energies ◽  
Cyclic Network ◽  
Ability To Drive

The geometries and energetics of molecular self-assembly structures that contain a sequential network of cyclic halogen-bonding interactions are investigated theoretically. The strength of the halogen-bonding interactions is assessed by examining binding energies, electron charge transfer (NBO analysis) and electron density at halogen-bond critical points (AIM theory). Specifically, structural motifs having intramolecular N—X...N (X= Cl, Br, or I) interactions and the ability to drive molecular self-assemblyviathe same type of interactions are used to construct larger self-assemblies of up to three unit motifs. N—X...N halogen-bond cooperativity as a function of the self-assembly size, and the nature of the halogen atom is also examined. The cyclic network of the halogen-bonding interactions provides a suitable cavity rich in electron density (from the halogen atom lone pairs not involved in the halogen bonds) that can potentially bind an electron-deficient species such as a metal ion. This possibility is explored by examining the ability of the N—X...N network to bind Na+. Likewise, molecular self-assembly structures driven by the weaker C—X...N halogen-bonding interactions are investigated and the results compared with those of their N—X...N counterparts.

Cooperative halogen bonding and polarized π-stacking in the formation of coloured charge-transfer co-crystals

2018 ◽  
Vol 42 (13) ◽  
pp. 10615-10622 ◽  
Author(s):  
Chideraa I. Nwachukwu ◽  
Zachary R. Kehoe ◽  
Nathan P. Bowling ◽  
Erin D. Speetzen ◽  
Eric Bosch
Keyword(s):  
Charge Transfer ◽  
Halogen Bond ◽  
Halogen Bonding ◽  
Π Stacking

Matched electron rich halogen bond acceptors and donor have been synthesized and the halogen bonded charge transfer cocrystals characterized.

Tetradentate halogen bonding macrocyclic anion receptor inspired by the “Texas-sized” molecular box

2022 ◽  
Author(s):  
Tian Zhao ◽  
Vincent Lynch ◽  
Jonathan L. Sessler
Keyword(s):  
Click Chemistry ◽  
Halogen Bond ◽  
Halogen Bonding ◽  
Anion Receptor

Inspired by the tetracationic “Texas-sized” molecular box, a neutral analogue containing four iodotriazole halogen bond-promoting subunits (“Ibox”) was synthesized. This new macrocycle was prepared by means of azide-alkyne click chemistry....

Halogen Bonding Organocatalysis Enhanced through Intramolecular Hydrogen Bonds

2022 ◽  
Author(s):  
Asia Marie S Riel ◽  
Daniel Adam Decato ◽  
Jiyu Sun ◽  
Orion Berryman
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Halogen Bond ◽  
Direct Interaction ◽  
Halogen Bonding ◽  
Intramolecular Hydrogen Bonds ◽  
Intramolecular Hydrogen

Recent results indicate a halogen bond donor is strengthened through direct interaction with a hydrogen bond to the electron-rich belt of the halogen. Here, this Hydrogen Bond enhanced Halogen Bond...

Halogen-Bonding Interaction between I2 and N-Iodosuccinimide in Lewis Base-Catalyzed Iodolactonization

2020 ◽  
Vol 22 (12) ◽  
pp. 4888-4892
Author(s):  
Takahiro Horibe ◽  
Yasutaka Tsuji ◽  
Kazuaki Ishihara
Keyword(s):  
Halogen Bonding ◽  
Lewis Base ◽  
Bonding Interaction
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