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Halogen bond : ウィキペディア英語版
Halogen bond
Halogen bonding (XB) is the non-covalent interaction that occurs between a halogen atom (Lewis acid) and a Lewis base. Although halogens are involved in other types of bonding (e.g. covalent), halogen bonding specifically refers to when the halogen acts as an electrophilic species.
==Bonding==
Comparison between hydrogen and halogen bonding:
:Hydrogen bonding: \mathrm
:Halogen bonding: \mathrm
In both cases, D (donor) is the atom, group, or molecule that is electron rich and donates them to the electron poor species (H or X). H is the hydrogen atom involved in hydrogen bonding (HB), and X is the halogen atom involved in XB. A (acceptor) is the electron poor species withdrawing the electron density from H or X, accordingly. H-A and X-A, when both atoms are considered together, are called hydrogen/halogen bond donors, accordingly, and D is HB/XB acceptor. A difference between HB and XB is since halogen atoms are Lewis bases, a halogen atom can both donate and accept in a halogen bond.
A parallel relationship can easily be drawn between halogen bonding and hydrogen bonding (HB). In both types of bonding, an electron donor/electron acceptor relationship exists. The difference between the two is what species can act as the electron donor/electron acceptor. In hydrogen bonding, a hydrogen atom acts as the electron acceptor and forms a non-covalent interaction by accepting electron density from an electron rich site (electron donor). In halogen bonding, a halogen atom is the electron acceptor. Simultaneously, the normal covalent bond between H or X and A weakens, so the electron density on H or X appears to be reduced. Electron density transfers results in a penetration of the van der Waals volumes.
Halogens participating in halogen bonding include: iodine (I), bromine (Br), chlorine (Cl), and sometimes fluorine (F). All four halogens are capable of acting as XB donors (as proven through theoretical and experimental data) and follow the general trend: F < Cl < Br < I, with iodine normally forming the strongest interactions.
Dihalogens (I2, Br2, etc.) tend to form strong halogen bonds. The strength and effectiveness of chlorine and fluorine in XB formation depend on the nature of the XB donor. If the halogen is bonded to an electronegative (electron withdrawing) moiety, it is more likely to form stronger halogen bonds.
For example, iodoperfluoroalkanes are well-designed for XB crystal engineering. In addition, this is also why F2 can act as a strong XB donor, but fluorocarbons are weak XB donors because the alkyl group connected to the fluorine is not electronegative. In addition, the Lewis base (XB acceptor) tends to be electronegative as well and anions are better XB acceptors than neutral molecules.
Halogen bonds are strong, specific, and directional interactions that give rise to well-defined structures. Halogen bond strengths range from 5–180 kJ/mol. The strength of XB allows it to compete with HB, which are a little bit weaker in strength. Halogen bonds tend to form at 180° angles, which was shown in Odd Hassel’s studies with bromine and 1,4-dioxane in 1954. Another contributing factor to halogen bond strength comes from the short distance between the halogen (Lewis acid, XB donor) and Lewis base (XB acceptor). The attractive nature of halogen bonds result in the distance between the donor and acceptor to be shorter than the sum of van der Waals radii. The XB interaction becomes stronger as the distance decreases between the halogen and Lewis base.

抄文引用元・出典: フリー百科事典『 ウィキペディア(Wikipedia)
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