halogens

Summary

Summary: A family of nonmetallic, generally electronegative, elements that form group 17 (formerly group VIIa) of the periodic table.

Top Publications

  1. Erdélyi M. Halogen bonding in solution. Chem Soc Rev. 2012;41:3547-57 pubmed publisher
    Halogen bonding is the electron density donation based weak interaction of halogens with Lewis bases...
  2. Grabowski S. Halogen bond and its counterparts: Bent's rule explains the formation of nonbonding interactions. J Phys Chem A. 2011;115:12340-7 pubmed publisher
    ..Numerous analogies between the halogen bond and the hydrogen bond are analyzed and various relationships between energetic, geometrical and the natural bond orbitals method (NBO) parameters are shown...
  3. Hardegger L, Kuhn B, Spinnler B, Anselm L, Ecabert R, Stihle M, et al. Halogen bonding at the active sites of human cathepsin?L and MEK1 kinase: efficient interactions in different environments. ChemMedChem. 2011;6:2048-54 pubmed publisher
    ..affinities were found to strongly increase when an aryl ring of the inhibitors is substituted with the larger halogens Cl, Br, and I, but to decrease upon F substitution...
  4. Xu Z, Liu Z, Chen T, Chen T, Wang Z, Tian G, et al. Utilization of halogen bond in lead optimization: a case study of rational design of potent phosphodiesterase type 5 (PDE5) inhibitors. J Med Chem. 2011;54:5607-11 pubmed publisher
    ..Our X-ray crystal structures verified the existence of the predicted halogen bonds, demonstrating that the halogen bond is an applicable tool in drug design and should be routinely considered in lead optimization...
  5. Del Bene J, Alkorta I, Elguero J. Do traditional, chlorine-shared, and ion-pair halogen bonds exist? An ab initio investigation of FCl:CNX complexes. J Phys Chem A. 2010;114:12958-62 pubmed publisher
    ..Coupling constants across halogen bonds are compared with corresponding coupling constants across traditional, proton-shared, and ion-pair hydrogen bonds...
  6. Prather M, McElroy M, Wofsy S. Reductions in ozone at high concentrations of stratospheric halogens. Nature. 1984;312:227-31 pubmed
    ..This could occur, for example by the middle of the next century, if emissions of man-made chlorocarbons were to grow at a rate of 3% per year. Ozone could be further depressed by release of industrial bromocarbon...
  7. Welz B, Lepri F, Araujo R, Ferreira S, Huang M, Okruss M, et al. Determination of phosphorus, sulfur and the halogens using high-temperature molecular absorption spectrometry in flames and furnaces--A review. Anal Chim Acta. 2009;647:137-48 pubmed publisher
    The literature about the investigation of molecular spectra of phosphorus, sulfur and the halogens in flames and furnaces, and the use of these spectra for the determination of these non-metals has been reviewed...
  8. Lu Y, Shi T, Wang Y, Yang H, Yan X, Luo X, et al. Halogen bonding--a novel interaction for rational drug design?. J Med Chem. 2009;52:2854-62 pubmed publisher
    ..This study would help to establish such interaction as a potential and effective tool in the context of drug design...
  9. Murray J, Lane P, Politzer P. Expansion of the sigma-hole concept. J Mol Model. 2009;15:723-9 pubmed publisher
    ..2) It is possible for the bonding orbital to be doubly-occupied and forming a coordinate covalent bond...

More Information

Publications62

  1. Politzer P, Lane P, Concha M, Ma Y, Murray J. An overview of halogen bonding. J Mol Model. 2007;13:305-11 pubmed
    ..Some computed XB interaction energies are presented and discussed. Mention is also made of the importance of halogen bonding in biological systems and processes, and in crystal engineering...
  2. Anderson J, Chapman S. Molecular mechanisms of enzyme-catalysed halogenation. Mol Biosyst. 2006;2:350-7 pubmed
    ..In addition, we will consider how this chemistry might be harnessed and developed to produce novel enzymatic activity...
  3. Vaillancourt F, Yeh E, Vosburg D, Garneau Tsodikova S, Walsh C. Nature's inventory of halogenation catalysts: oxidative strategies predominate. Chem Rev. 2006;106:3364-78 pubmed
  4. Röling W. Do microbial numbers count? Quantifying the regulation of biogeochemical fluxes by population size and cellular activity. FEMS Microbiol Ecol. 2007;62:202-10 pubmed
    ..Its application is discussed in the context of the complexity of microbial communities (e.g. functional redundancy) and their functioning...
  5. Neumann C, Fujimori D, Walsh C. Halogenation strategies in natural product biosynthesis. Chem Biol. 2008;15:99-109 pubmed publisher
    ..In this article, we review the current state of knowledge regarding the mechanisms of these transformations, highlight applications of this knowledge, and propose future opportunities and challenges for the field...
  6. Clark T, Hennemann M, Murray J, Politzer P. Halogen bonding: the sigma-hole. Proceedings of "Modeling interactions in biomolecules II", Prague, September 5th-9th, 2005. J Mol Model. 2007;13:291-6 pubmed
    ..Thus a sigma-hole is observed for the Cl in CF(3)Cl, but not in CH(3)Cl...
  7. Valinluck V, Wu W, Liu P, Neidigh J, Sowers L. Impact of cytosine 5-halogens on the interaction of DNA with restriction endonucleases and methyltransferase. Chem Res Toxicol. 2006;19:556-62 pubmed
    ..a series of oligonucleotides containing cytosine and a series of 5-substituted cytosine analogues including all halogens. This set of oligonucleotides has been used to probe the relationship between the size of the substituent and its ..
  8. Butler A, Sandy M. Mechanistic considerations of halogenating enzymes. Nature. 2009;460:848-54 pubmed publisher
  9. Lu Y, Wang Y, Zhu W. Nonbonding interactions of organic halogens in biological systems: implications for drug discovery and biomolecular design. Phys Chem Chem Phys. 2010;12:4543-51 pubmed publisher
    ..In this Perspective, we concentrate on nonbonding interactions of halogens from both crystallographic data and theoretical viewpoints...
  10. Ohshiro T, Littlechild J, Garcia Rodriguez E, Isupov M, Iida Y, Kobayashi T, et al. Modification of halogen specificity of a vanadium-dependent bromoperoxidase. Protein Sci. 2004;13:1566-71 pubmed
    ..These results supported the existence of a specific halogen binding site within the catalytic cleft of vanadium haloperoxidases...
  11. Auffinger P, Hays F, Westhof E, Ho P. Halogen bonds in biological molecules. Proc Natl Acad Sci U S A. 2004;101:16789-94 pubmed
    ..Thus, the specific geometry and diversity of the interacting partners of halogen bonds offer new and versatile tools for the design of ligands as drugs and materials in nanotechnology...
  12. Weyand M, Hecht H, Kiess M, Liaud M, Vilter H, Schomburg D. X-ray structure determination of a vanadium-dependent haloperoxidase from Ascophyllum nodosum at 2.0 A resolution. J Mol Biol. 1999;293:595-611 pubmed
  13. de Jong R, Dijkstra B. Structure and mechanism of bacterial dehalogenases: different ways to cleave a carbon-halogen bond. Curr Opin Struct Biol. 2003;13:722-30 pubmed
    ..The available information on the various dehalogenases supports different views on the possible evolutionary origins of their activities...
  14. Adams H, Cockroft S, Guardigli C, Hunter C, Lawson K, Perkins J, et al. Experimental measurement of noncovalent interactions between halogens and aromatic rings. Chembiochem. 2004;5:657-65 pubmed
    Chemical double mutant cycles have been used to quantify the interactions of halogens with the faces of aromatic rings in chloroform...
  15. van Pee K, Dong C, Flecks S, Naismith J, Patallo E, Wage T. Biological halogenation has moved far beyond haloperoxidases. Adv Appl Microbiol. 2006;59:127-57 pubmed
  16. Winter J, Moore B. Exploring the chemistry and biology of vanadium-dependent haloperoxidases. J Biol Chem. 2009;284:18577-81 pubmed publisher
  17. Del Bene J, Alkorta I, Sánchez Sanz G, Elguero J. Structures, binding energies, and spin-spin coupling constants of geometric isomers of pnicogen homodimers (PHFX)2, X = F, Cl, CN, CH3, NC. J Phys Chem A. 2012;116:3056-60 pubmed publisher
    ..Of these, isomers having F-P···P-F linear are the most stable. Binding energies, intermolecular distances, and EOM-CCSD spin-spin coupling constants are sensitive to both the nature of X and the atoms that assume the linear alignment...
  18. Krygowski T, Oziminski W, Cyrański M. Aromatic character of heptafulvene and its complexes with halogen atoms. J Mol Model. 2012;18:2453-60 pubmed publisher
    Geometry optimization of heptafulvene-halogen complexes (halogens: F, Cl, Br, I, and At) carried out at the B3LYP/6-311+G(d,p) level of theory allowed us to estimate the geometry-based aromaticity index HOMA, the magnetism-based indices ..
  19. Irudayam S, Henchman R. Long-range hydrogen-bond structure in aqueous solutions and the vapor-water interface. J Chem Phys. 2012;137:034508 pubmed publisher
    ..Rather than being confined close to the solute, it is spread over as many water molecules as possible, presumably to minimize the perturbation to each water molecule...
  20. Cai Y, Liu X, Zhou P, Kuang Y, Lin L, Feng X. Iron-catalyzed asymmetric haloamination reactions. Chem Commun (Camb). 2013;49:8054-6 pubmed publisher
    ..This iron catalyst also exhibits perfect enantioselectivity for chalcone derivatives. The cooperative activation of the substrate and the reagent in concert guarantees the high stereoselectivity...
  21. Lu Y, Liu Y, Li H, Zhu X, Liu H, Zhu W. Mutual influence between halogen bonds and cation-? interactions: a theoretical study. Chemphyschem. 2012;13:2154-61 pubmed publisher
    ..Finally, experimental evidence for a combination of the two interactions is obtained from the Cambridge Structural Database...
  22. Nagaki A, Moriwaki Y, Haraki S, Kenmoku A, Takabayashi N, Hayashi A, et al. Cross-coupling of aryllithiums with aryl and vinyl halides in flow microreactors. Chem Asian J. 2012;7:1061-8 pubmed publisher
    ..Pd(OAc)(2) was an effective catalyst, and the space integration of the Br/Li exchange of ArBr with BuLi and the Murahashi coupling with vinyl halides was successfully achieved...
  23. Nagashima Y, Takita R, Yoshida K, Hirano K, Uchiyama M. Design, generation, and synthetic application of borylzincate: borylation of aryl halides and borylzincation of benzynes/terminal alkyne. J Am Chem Soc. 2013;135:18730-3 pubmed publisher
    ..This enabled Zn-catalyzed borylation of aryl halides and borylzincation of benzynes and terminal alkyne from diborons without the need for any cocatalyst. ..
  24. Li Q, Ma S, Liu X, Li W, Cheng J. Cooperative and substitution effects in enhancing strengths of halogen bonds in FCl···CNX complexes. J Chem Phys. 2012;137:084314 pubmed publisher
    ..The atoms in molecules and natural bond orbital analyses have been carried out for these complexes to understand the nature of halogen bond and the origin of the cooperativity...
  25. Carter M, Voth A, Scholfield M, Rummel B, Sowers L, Ho P. Enthalpy-entropy compensation in biomolecular halogen bonds measured in DNA junctions. Biochemistry. 2013;52:4891-903 pubmed publisher
    Interest in noncovalent interactions involving halogens, particularly halogen bonds (X-bonds), has grown dramatically in the past decade, propelled by the use of X-bonding in molecular engineering and drug design...
  26. Kostal J, Voutchkova Kostal A, Weeks B, Zimmerman J, Anastas P. A free energy approach to the prediction of olefin and epoxide mutagenicity and carcinogenicity. Chem Res Toxicol. 2012;25:2780-7 pubmed publisher
  27. Snyder S, Treitler D, Brucks A. Simple reagents for direct halonium-induced polyene cyclizations. J Am Chem Soc. 2010;132:14303-14 pubmed publisher
    ..Preliminary attempts to use chiral forms of the reagent class for enantioselective alkene halogenation are also described...
  28. Chu S, Letcher R. Halogenated phenolic compound determination in plasma and serum by solid phase extraction, dansylation derivatization and liquid chromatography-positive electrospray ionization-tandem quadrupole mass spectrometry. J Chromatogr A. 2013;1320:111-7 pubmed publisher
    ..The method was successfully applied for HPC determination in representative polar bear and snapping turtle plasma samples. ..
  29. Honeker R, Garza Sanchez R, Hopkinson M, Glorius F. Visible-Light-Promoted Trifluoromethylthiolation of Styrenes by Dual Photoredox/Halide Catalysis. Chemistry. 2016;22:4395-9 pubmed publisher
    ..Inexpensive halide salts play a crucial role in activating the trifluoromethylthiolating reagent towards photoredox catalysis and aid the formation of the SCF3 radical. ..
  30. Vardhaman A, Barman P, Kumar S, Sastri C, Kumar D, de Visser S. Mechanistic insight into halide oxidation by non-heme iron complexes. Haloperoxidase versus halogenase activity. Chem Commun (Camb). 2013;49:10926-8 pubmed publisher
    ..We show that while iron(III)-hydroperoxo complexes oxidise halides via oxygen atom transfer, the corresponding iron(IV)-oxo complex reacts via electron transfer...
  31. Yao B, Wang Z, Zhang H, Wang D, Zhao L, Wang M. Cu(ClO(4))(2)-mediated arene C-H bond halogenations of azacalixaromatics using alkali metal halides as halogen sources. J Org Chem. 2012;77:3336-40 pubmed publisher
  32. Ou Y, Jiao N. Recyclable copper catalyzed nitrogenation of biphenyl halides: a direct approach to carbazoles. Chem Commun (Camb). 2013;49:3473-5 pubmed publisher
    ..A recyclable and inexpensive Cu-catalyst was successfully employed in N-heterocyclic compound synthesis via tandem azidation and C-H amination, which makes this protocol very practical and easy to handle...
  33. Dudnik A, Fu G. Nickel-catalyzed coupling reactions of alkyl electrophiles, including unactivated tertiary halides, to generate carbon-boron bonds. J Am Chem Soc. 2012;134:10693-7 pubmed publisher
  34. Yang Y, Buchwald S. Ligand-controlled palladium-catalyzed regiodivergent Suzuki-Miyaura cross-coupling of allylboronates and aryl halides. J Am Chem Soc. 2013;135:10642-5 pubmed publisher
    ..These methods allow for the highly selective preparation of either the ?- or the ?-isomeric coupling product. ..
  35. Baldrighi M, Cavallo G, Chierotti M, Gobetto R, Metrangolo P, Pilati T, et al. Halogen bonding and pharmaceutical cocrystals: the case of a widely used preservative. Mol Pharm. 2013;10:1760-72 pubmed publisher
    ..The cocrystal involving the GRAS excipient CaCl2 has superior powder flow characteristics compared to the pure IPBC, representing a promising solution to the handling issues related to the manufacturing of products containing IPBC...
  36. Grigg R, Van Hoveln R, Schomaker J. Copper-catalyzed recycling of halogen activating groups via 1,3-halogen migration. J Am Chem Soc. 2012;134:16131-4 pubmed publisher
  37. Chudzinski M, McClary C, Taylor M. Anion receptors composed of hydrogen- and halogen-bond donor groups: modulating selectivity with combinations of distinct noncovalent interactions. J Am Chem Soc. 2011;133:10559-67 pubmed publisher
    ..Cooperation between two distinct noncovalent interactions leads to unusual effects on receptor selectivity, a result of fundamental differences in the interactions of halogen- and hydrogen-bond donor groups with anions...
  38. Chen D, Cao Y, Yuan Z, Cai H, Zheng R, Kong L, et al. Synthesis of cis-1,2-dihaloalkenes featuring palladium-catalyzed coupling of haloalkynes and ?,?-unsaturated carbonyls. J Org Chem. 2011;76:4071-4 pubmed publisher
    ..This method was subsequently applied to synthesize the functionalized conjugated enyne via the mono-Sonogashira coupling reaction of cis-1-chloro-2-iodoalkene...
  39. Jenkins H, Glasser L, Lee J. Volume-based thermoelasticity: consequences of the (near) proportionality of isothermal compressibility to formula-unit volume. Inorg Chem. 2010;49:9978-84 pubmed publisher
    ..These results confirm the conclusion that volume is intimately linked to thermodynamic quantities, as already demonstrated by our development of volume-based thermodynamics (VBT)...
  40. McMullin C, Jover J, Harvey J, Fey N. Accurate modelling of Pd(0) + PhX oxidative addition kinetics. Dalton Trans. 2010;39:10833-6 pubmed publisher
    ..Barrios-Landeros, B. P. Carrow and J. F. Hartwig, J. Am. Chem. Soc., 2009, 131, 8141-8154). The calculated activation free energies agree near-quantitatively with experimentally observed rate constants...
  41. Čobeljić B, Milenković M, Pevec A, Turel I, Vujčić M, Janović B, et al. Investigation of antitumor potential of Ni(II) complexes with tridentate PNO acylhydrazones of 2-(diphenylphosphino)benzaldehyde and monodentate pseudohalides. J Biol Inorg Chem. 2016;21:145-62 pubmed publisher
    ..The observed selectivity of the azido complex for some tumor cell lines can be connected with its strong DNA damaging activity. ..
  42. Geduhn J, Dove S, Shen Y, Tang W, Konig B, Seifert R. Bis-halogen-anthraniloyl-substituted nucleoside 5'-triphosphates as potent and selective inhibitors of Bordetella pertussis adenylyl cyclase toxin. J Pharmacol Exp Ther. 2011;336:104-15 pubmed publisher
    ..Collectively, we have identified the first potent CyaA inhibitor with high selectivity relative to mammalian ACs. The fluorescence properties of bis-ANT nucleotides facilitate development of a high-throughput screening assay...
  43. Serpe L, Ellena S, Barbero N, Foglietta F, Prandini F, Gallo M, et al. Squaraines bearing halogenated moieties as anticancer photosensitizers: Synthesis, characterization and biological evaluation. Eur J Med Chem. 2016;113:187-97 pubmed publisher
    ..001), which leads to necrosis 6 h after treatment. Induction of cytochrome c release, DNA damage and up-regulation of GPX1, NQO1 and SOD2 mRNA gene expression after PDT were investigated. ..
  44. Güssregen S, Matter H, Hessler G, Müller M, Schmidt F, Clark T. 3D-QSAR based on quantum-chemical molecular fields: toward an improved description of halogen interactions. J Chem Inf Model. 2012;52:2441-53 pubmed
    ..This will allow such knowledge to be used to design novel molecules on the basis of interactions additional to steric and hydrogen-bonding features...
  45. Dobish M, Johnston J. Achiral counterion control of enantioselectivity in a Brønsted acid-catalyzed iodolactonization. J Am Chem Soc. 2012;134:6068-71 pubmed publisher
    ..In this way, unsaturated carboxylic acids are converted to ?-lactones in high yields (up to 98% ee) using commercially available NIS...
  46. Emmett E, Richards Taylor C, Nguyen B, Garcia Rubia A, Hayter B, Willis M. Palladium-catalysed aminosulfonylation of aryl-, alkenyl- and heteroaryl halides: scope of the three-component synthesis of N-aminosulfonamides. Org Biomol Chem. 2012;10:4007-14 pubmed publisher
    ..The ability to employ hydrazine·SO(2) complexes as both the N-nucleophile and SO(2) source is also illustrated...
  47. Petrov P, Virovets A, Alberola A, Llusar R, Konchenko S. Unexpected transformation of a diamagnetic Mo3(?3-S)(?-S)3 to a paramagnetic Mo3(?3-S)2(?-S)3 cluster core by reaction of [Mo3S4(dppe)3Br3]PF6 with (t)BuSNa. Dalton Trans. 2010;39:8875-7 pubmed publisher
  48. Poineau F, Malliakas C, Weck P, Scott B, Johnstone E, Forster P, et al. Technetium dichloride: a new binary halide containing metal-metal multiple bonds. J Am Chem Soc. 2011;133:8814-7 pubmed publisher
    ..The metal-metal separation in the prisms is 2.127(2) Å, a distance consistent with the presence of a Tc?Tc triple bond that is also supported by electronic structure calculations...
  49. Urner M, Limbach L, Herrmann I, Müller Edenborn B, Roth Z graggen B, Schlicker A, et al. Fluorinated groups mediate the immunomodulatory effects of volatile anesthetics in acute cell injury. Am J Respir Cell Mol Biol. 2011;45:617-24 pubmed publisher
  50. Bresme F, Chacón E, Tarazona P, Wynveen A. The structure of ionic aqueous solutions at interfaces: an intrinsic structure analysis. J Chem Phys. 2012;137:114706 pubmed
  51. Palisse A, Kirsch S. Metal-free reactions of alkynes via electrophilic iodocarbocyclizations. Org Biomol Chem. 2012;10:8041-7 pubmed
    ..Primarily guided by the type of carbon nucleophile, methods are categorized as the addition of arene, malonate, and olefin nucleophiles...
  52. Inyang E, Taleatu B, Oketayo O, Mokobia C, Adenodi R, Balogun E. Characterizing thermoluminescence properties of calcium halophosphate fluorescent coating powder for radiation dosimetry. J Environ Sci Eng. 2011;53:1-6 pubmed
    ..This material can also find application in radiation therapy associated with very high accident dosimetry as well as in material testing...
  53. Zhao D, Gao C, Su X, He Y, You J, Xue Y. Copper-catalyzed decarboxylative cross-coupling of alkynyl carboxylic acids with aryl halides. Chem Commun (Camb). 2010;46:9049-51 pubmed publisher
    ..Benzofurans could be further prepared smoothly by a one-pot domino protocol on the basis of decarboxylative cross-coupling of 2-iodophenol...