Novel Halogen-Bonded Complexes H<sub>3</sub>NBH<sub>3</sub>···XY (XY = ClF, ClCl, BrF, BrCl, and BrBr): Partially Covalent Character

An, Xiulin; Jing, Bo

doi:10.1021/jp101732c

Cited by 36 publications

(34 citation statements)

References 46 publications

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“…Furthermore, "like-attracting-like" was observed (24) just as with halogens; the outer portion of a sulfur in one molecule interacting attractively with the side of a sulfur in another, identical molecule. [151] In 2007 it was confirmed computationally that covalently bonded atoms of Group VI could have positive s holes on the extensions of the bonds, [86] and this was later also demonstrated for Groups V [163] and IV. [164] Their presence can again be attributed to the atoms' anisotropic charge distributions.…”

Section: S-hole Interactions Of Group Iv-vi Atomsmentioning

confidence: 95%

“…As we have just seen, the negative lateral sides of another covalently bonded halogen atom can play this role. The p electrons of unsaturated molecules-in arenes, [58,[77][78][79][80] alkenes, alkynes, [81,82] and so forthcan serve this purpose, as can anions, [83,84] hydrides, [85][86][87] and so forth. These are all simply examples of halogen bonding.…”

Section: Halogen-bonded Complexesmentioning

confidence: 99%

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Halogen Bonding: An Interim Discussion

2013

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Halogen bonding is a noncovalent interaction that is receiving rapidly increasing attention because of its significance in biological systems and its importance in the design of new materials in a variety of areas, for example, electronics, nonlinear optical activity, and pharmaceuticals. The interactions can be understood in terms of electrostatics/polarization and dispersion; they involve a region of positive electrostatic potential on a covalently bonded halogen and a negative site, such as the lone pair of a Lewis base. The positive potential, labeled a σ hole, is on the extension of the covalent bond to the halogen, which accounts for the characteristic near-linearity of halogen bonding. In many instances, the lateral sides of the halogen have negative electrostatic potentials, allowing it to also interact favorably with positive sites. In this discussion, after looking at some of the experimental observations of halogen bonding, we address the origins of σ holes, the factors that govern the magnitudes of their electrostatic potentials, and the properties of the resulting complexes with negative sites. The relationship of halogen and hydrogen bonding is examined. We also point out that σ-hole interactions are not limited to halogens, but can also involve covalently bonded atoms of Groups IV-VI. Examples of applications in biological/medicinal chemistry and in crystal engineering are mentioned, taking note that halogen bonding can be "tuned" to fit various requirements, that is, strength of interaction, steric factors, and so forth.

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Section: S-hole Interactions Of Group Iv-vi Atomsmentioning

confidence: 95%

Section: Halogen-bonded Complexesmentioning

confidence: 99%

Halogen Bonding: An Interim Discussion

2013

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“…The NBO analysis [20,[68][69][70][71][72] stresses the role of intermolecular orbital interaction in the complex, particularly charge transfer, the second-order perturbation energy lowering (D 2 E) can be taken as an index to judge the strength of hydrogen bonds. For a better understanding of halogen bonds, NBO calculations were carried out for the complexes optimized at the HF/aug-cc-pVDZ//MP2(full)/ aug-cc-pVDZ level.…”

Section: Natural Bond Orbital Analysismentioning

confidence: 99%

A computational study on the nature of the halogen bond between sulfides and dihalogen molecules

Zhang

Zeng

et al. 2011

Struct Chem

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The characteristics and nature of the halogen bonding in a series of BÁÁÁXY (B = H 2 S, H 2 CS, (CH 2 ) 2 S; XY = ClF, Cl 2 , BrF, BrCl, Br 2 ) complexes were analyzed by means of the quantum theory of ''atoms in molecules'' (QTAIM) and ''natural bond orbital'' (NBO) methodology at the second-order Møller-Plesset (MP2) level. Electrostatic potential, bond length, interaction energy, topological properties of the electron density, the dipole moment, and the charge transfer were investigated systematically. For the same electron donor, the interaction energies follows the BÁÁÁBrF [ BÁÁÁClF [ BÁÁÁBrCl [ BÁÁÁBr 2 [ BÁÁÁCl 2 [ BÁÁÁClBr order. For the same electron acceptor, the interaction energies increase in the sequence of H 2 S, H 2 CS, and (CH 2 ) 2 S. Topological analyses show these halogen bonding interactions belong to weak interactions with an electrostatic nature. It was found that the strength of the halogen-bonding interaction correlates well with the electrostatic potential associated with halogen atom and the amount of charge transfer from sulfides to dihalogen molecules, indicating that electrostatic interaction plays an important role in these halogen bonds. Charge transfer is also an important factor in the halogen bonds involved with dihalogen molecules.Keywords Halogen bond Á Topological analysis of electron density Á Natural bond orbital analysis Á Electrostatic interaction Á Charge transfer

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“…[2][3][4] The hydrogen bonds in these base pairs and wobble base pairs have been a target for researchers over the years. 17,[38][39][40][41] Though HBs are stronger than XBs, some of the stronger XBs are reported in the literature and generally the strength of the XBs lies in the range of 5 to 180 kJ mol À1 . On the other hand, a relatively less characterized form of intermolecular interactions that attract much attention in literature is the halogen bond (XB).…”

Section: Introductionmentioning

confidence: 97%

A new turn in codon–anticodon selection through halogen bonds

Solomon

Vedha

Venuvanalingam

2014

Phys. Chem. Chem. Phys.

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The halogen bond is relatively a less characterized intermolecular interaction compared to the hydrogen bond and the structure, stability and electronic structures of halogenated base pairs, particularly at the wobble junction have been investigated using DFT. Three halogens, namely Cl, Br and I, have been tested for their role in such situations with uracil as the anticodon base. Computed results reveal that when halogen atoms replace protons in the hydrogen bonding positions they induce lot of geometric changes that flip some of the observed base pairs into unobserved base pairs and vice versa. NCI, NBO and AIM analyses explain these changes at the electronic level. The new codons will have lot of impact in future applications, particularly in self assembly of biomaterials and t-RNA synthetic strategies.

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Novel Halogen-Bonded Complexes H₃NBH₃···XY (XY = ClF, ClCl, BrF, BrCl, and BrBr): Partially Covalent Character

Cited by 36 publications

References 46 publications

Halogen Bonding: An Interim Discussion

Halogen Bonding: An Interim Discussion

A computational study on the nature of the halogen bond between sulfides and dihalogen molecules

A new turn in codon–anticodon selection through halogen bonds

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Novel Halogen-Bonded Complexes H3NBH3···XY (XY = ClF, ClCl, BrF, BrCl, and BrBr): Partially Covalent Character

Cited by 36 publications

References 46 publications

Halogen Bonding: An Interim Discussion

Halogen Bonding: An Interim Discussion

A computational study on the nature of the halogen bond between sulfides and dihalogen molecules

A new turn in codon–anticodon selection through halogen bonds

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Product

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Novel Halogen-Bonded Complexes H₃NBH₃···XY (XY = ClF, ClCl, BrF, BrCl, and BrBr): Partially Covalent Character