2006
DOI: 10.1007/s00894-006-0130-2
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Abstract: Halogen bonding refers to the non-covalent interactions of halogen atoms X in some molecules, RX, with negative sites on others. It can be explained by the presence of a region of positive electrostatic potential, the sigma-hole, on the outermost portion of the halogen's surface, centered on the R-X axis. We have carried out a natural bond order B3LYP analysis of the molecules CF(3)X, with X = F, Cl, Br and I. It shows that the Cl, Br and I atoms in these molecules closely approximate the [Formula: see text] c… Show more

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Cited by 2,035 publications
(1,955 citation statements)
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“…σ-Hole interactions [10][11][12] represent a relatively recent entry into the canon of weak bonds [13][14][15], but following the seminal papers of P. Politzer et al [16,17], these interactions rapidly became popular targets for studies in this field [15,[18][19][20]. A covalently bonded atom characteristically has a region of low electron density, known as the Bσ-hole,ŵ hich is usually located along the extension of the covalent bond but on the opposite side of the atom to the bond.…”
Section: Introductionmentioning
confidence: 99%
“…σ-Hole interactions [10][11][12] represent a relatively recent entry into the canon of weak bonds [13][14][15], but following the seminal papers of P. Politzer et al [16,17], these interactions rapidly became popular targets for studies in this field [15,[18][19][20]. A covalently bonded atom characteristically has a region of low electron density, known as the Bσ-hole,ŵ hich is usually located along the extension of the covalent bond but on the opposite side of the atom to the bond.…”
Section: Introductionmentioning
confidence: 99%
“…It has been generally accepted that due to anisotropy of halogen atoms, the partial positive charge occurs in the region of halogen valence sphere being placed opposite to the covalent bond linking the halogen atom with its adjacent atom (usually it is the carbon atom or another halogen atom, but not the hydrogen atom). This partial positive charge on the valence sphere of the halogen atom is often defined within the framework of NBO theory [21] as a sigma hole-a local deficit of an electron charge (a hole) being placed opposite the sigma bond [22,23]. The sigma hole may interact with the local electron charge surplus such as lone electron pairs [17,24,25], pi-type electrons [17,24,26], or even sigma-type electrons [27]; in this way, the mechanism of formation of X-bond can be well defined.…”
Section: Introductionmentioning
confidence: 99%
“…This structure-activity relationship is reflected in the EC 50 values for compound I-6 (EC 50 =35.79±1.37 nmol/L), compound I-8 (EC 50 =14.01±1.84 nmol/L) and compound I-10 (EC 50 =9.57±0.19 nmol/L). This phenomenon is potentially explained by the existence of a halogen atom that reduces the electron density on the benzene ring given its electron-withdrawing property and further promotes the interaction between the compounds and the receptor amino acid residues, thereby increasing the KOR stimulation action [26] . SAR studies indicate that the small size of the amide group in the R1 group and a halogen atom in the R3 group are essential for KOR stimulation in this group.…”
Section: Discussionmentioning
confidence: 99%
“…Alkyl residues, which are considered electron-donating groups, improve receptor and molecule binding by increasing the electron density of the benzene ring [28] . Contrary to alkyl groups, chlorine atoms, which serve as electron-withdrawing groups, display the opposite effect [26] . Based on the SAR studies, the phenylamine with an alkyl group in the R group of group II compounds plays a definitive role in KOR stimulation.…”
Section: Discussionmentioning
confidence: 99%