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.

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.

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.

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.

Second hyperpolarizability of multimetallocenes [Cp–Mn–Cp] of Be, Mg and Ca

2015 ◽  
Vol 14 (01) ◽  
pp. 1550002 ◽  
Author(s):  
Kaushik Hatua ◽  
Prasanta K. Nandi
Keyword(s):  
Charge Transfer ◽  
Theoretical Study ◽  
Small Variation ◽  
Cooperative Effect ◽  
Second Hyperpolarizability ◽  
Nlo Property ◽  
Metal Atoms ◽  
Bonding Interaction ◽  
Charge Transfer Transitions ◽  
The Difference

Multimetallocene complexes ( Cp – M n– Cp ) of Be , Mg and Ca have been considered for the theoretical study of static second hyperpolarizability using a number of DFT functionals. Owing to the cooperative effect in bonding, beryllium forms multiberyllocene complexes ( Cp – Be n– Cp ) which have sufficient thermal stability with respect to dissociation into neutral fragments up to n = 10. On the other hand, multimetallocene complexes of Mg and Ca are found to be stable for n ≤ 5 which may be due to the weaker covalent bonding interaction between the larger metal atoms. The rather small variation of linear and cubic polarizabilities of Cp – Be n– Cp complexes beyond n = 5 arises from the rather weaker charge transfer transitions. The difference in NLO property among the investigated metal complexes arises from the extent of charge transfer from the terminal metal atoms and the distance between them. The charge transfer at longer distances in the ground state of Mg and Ca complexes leads to more intense electronic transition — the spectroscopic parameters of which strongly favors the enhancement of second hyperpolarizability.

Reagents that Contain Se-H or Te-H Bonds

2018 ◽  
Vol 4 (1) ◽  
Author(s):  
Peter C. Ho ◽  
Jin Wang ◽  
Ignacio Vargas-Baca
Keyword(s):  
Alkali Metal ◽  
Nucleophilic Substitution ◽  
Organic Compounds ◽  
High Reactivity ◽  
Unsaturated Compounds

Abstract Species that contain bonds between hydrogen and selenium or tellurium have a characteristic high reactivity, which can be harnessed in the synthesis of valuable organic compounds. This overview includes the synthesis of dihydrides, alkali metal hydrochalcogenides, chalcogenols, chalcogenocarboxylic and chalcogenocarbamic acids, and their application in reactions of reduction, addition to unsaturated compounds, and nucleophilic substitution.

Theoretical Study of Nucleophilic Substitution at Two-Coordinate Sulfur

2001 ◽  
Vol 66 (6) ◽  
pp. 2005-2010 ◽  
Author(s):  
Steven M. Bachrach ◽  
BettyCep D. Gailbreath
Keyword(s):  
Nucleophilic Substitution ◽  
Theoretical Study
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