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Solid-State NMR Study of Halogen-Bonded Adducts

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Halogen Bonding I

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 358))

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References

  1. Alkorta I, Elguero J, Denisov GS (2008) A review with comprehensive data on experimental indirect scalar NMR spin-spin coupling constants across hydrogen bonds. Magn Reson Chem 46:599

    Article  CAS  Google Scholar 

  2. Aliev AE (2004) Probing hydrogen bonding in solids using solid state NMR spectroscopy. Struct Bond 108:1

    Article  CAS  Google Scholar 

  3. Brunner E, Sternberg U (1998) Solid-state NMR investigations on the nature of hydrogen bonds. Prog Nucl Magn Reson Spectrosc 32:21

    Article  CAS  Google Scholar 

  4. Wu G, Freure CJ, Verdurand E (1998) Proton chemical shift tensors and hydrogen bond geometry: a 1H-2H dipolar NMR study of the water molecule in crystalline hydrates. J Am Chem Soc 120:13187

    Article  CAS  Google Scholar 

  5. Bryce DL, Adiga S, Elliott EK, Gokel GW (2006) Solid-state 23Na NMR study of sodium lariat ether receptors exhibiting cation-π interactions. J Phys Chem A 110:13568

    Article  CAS  Google Scholar 

  6. Lee PK, Chapman RP, Zhang L, Hu J, Barbour LJ, Elliott EK, Gokel GW, Bryce DL (2007) K-39 quadrupolar and chemical shift tensors for organic potassium complexes and diatomic molecules. J Phys Chem A 111:12859

    Article  CAS  Google Scholar 

  7. Plevin MJ, Bryce DL, Boisbouvier J (2010) Direct detection of CH/π interactions in proteins. Nat Chem 2:466

    Article  CAS  Google Scholar 

  8. Desiraju GR, Ho PS, Kloo L, Legon AC, Marquardt R, Metrangolo P, Politzer P, Resnati G, Rissanen K (2013) Definition of the halogen bond (IUPAC recommendations 2013). Pure Appl Chem 85:1711

    Article  CAS  Google Scholar 

  9. Bryce DL (2012) Halogen bonding. Chem Int 34:27

    Google Scholar 

  10. Larsen DW, Allred AL (1965) Halogen complexes. III. The association of 2,4,6-trimethylpyridine and trifluoroiodomethane. J Phys Chem 69:2400

    Article  CAS  Google Scholar 

  11. Bruno TJ, Martire DE, Harbison MWP, Nikolić A, Hammer CF (1983) Gas-liquid chromatographic and nuclear magnetic resonance study of haloform + di-n-alkyl ether + n-alkane mixtures at 30°C. J Phys Chem 87:2430

    Article  CAS  Google Scholar 

  12. Martire DE, Sheridan JP, King JW, O’Donnell SE (1976) Thermodynamics of molecular association. 9. An NMR study of hydrogen bonding of CHCl3 and CHBr3 to di-n-octyl ether, di-n-octyl thioether, and di-n-octylmethylamine. J Am Chem Soc 98:3101

    Article  CAS  Google Scholar 

  13. Green RD, Martin JS (1968) Anion-molecule complexes in solution. I. Nuclear magnetic resonance and infrared studies of halide ion-trihalomethane association. J Am Chem Soc 90:3659

    Article  CAS  Google Scholar 

  14. Bertrán JF, Rodríguez M (1979) Detection of halogen bond formation by correlation of proton solvent shifts. 1. Haloforms in n-Electron Donor Solvents. Org Magn Reson 12:92

    Article  Google Scholar 

  15. Bertrán JF, Rodríguez M (1980) Detection of halogen bond formation by correlation of proton solvent shifts. II - Methlyene Halides in n-Electron Donor Solvents. Org Magn Reson 14:244

    Article  Google Scholar 

  16. Messina MT, Metrangolo P, Panzeri W, Ragg E, Resnati G (1998) Perfluorocarbon-hydrocarbon self-assembly. Part 3. Liquid phase interactions between perfluoroalkylhalides and heteroatom containing hydrocarbons. Tetrahedron Lett 39:9069

    Article  CAS  Google Scholar 

  17. Metrangolo P, Panzeri W, Recupero F, Resnati G (2002) Perfluorocarbon-hydrocarbon self-assembly. Part 16. 19F NMR study of the halogen bonding between halo-perfluorocarbons and heteroatom containing hydrocarbons. J Fluor Chem 114:27

    Article  CAS  Google Scholar 

  18. Messina MT, Metrangolo P, Navarrini W, Radice S, Resnati G, Zerbi G (2000) Infrared and Raman analyses of the halogen-bonded non-covalent adducts formed by α, ω-diiodoperfluoroalkanes with DABCO and other electron donors. J Mol Struct 524:87

    Article  CAS  Google Scholar 

  19. Tiers GVD (2000) Detection of oriented association via NMR dilution shifts in tetramethylsilane solvent. 4. Temperature coefficients for perfluoroalkyl halide systems. J Fluor Chem 102:175

    Google Scholar 

  20. Löhr H-G, Engel A, Josel H-P, Vögtle F, Schuh W, Puff H (1984) Three-dimensional linkage by electron donor-acceptor interactions: complexes of organic ammonium halides with triiodomethane. J Org Chem 49:1621

    Article  Google Scholar 

  21. Rege PD, Malkina OL, Goroff NS (2002) The effect of Lewis bases on the 13C NMR of iodoalkynes. J Am Chem Soc 124:370

    Article  CAS  Google Scholar 

  22. Glaser R, Chen N, Wu H, Knotts N, Kaupp M (2004) 13C NMR study of halogen bonding of haloarenes: measurements of solvent effects and theoretical analysis. J Am Chem Soc 126:4412

    Article  CAS  Google Scholar 

  23. Sarwar MG, Dragisic B, Salsberg LJ, Gouliaras C, Taylor MS (2010) Thermodynamics of halogen bonding in solution: substituent, structural, and solvent effects. J Am Chem Soc 132:1646

    Article  CAS  Google Scholar 

  24. Sarwar MG, Dragisic B, Sagoo S, Taylor MS (2010) A tridentate halogen-bonding receptor for tight binding of halide anions. Angew Chem Int Ed 49:1674

    Article  CAS  Google Scholar 

  25. Carlsson A-CC, Gräfenstein J, Laurila JL, Bergquist J, Erdélyi M (2012) Symmetry of [N-X-N]+ halogen bonds in solution. Chem Commun 48:1458

    Article  CAS  Google Scholar 

  26. Carlsson A-CC, Gräfenstein J, Budnjo A, Laurila JL, Bergquist J, Karim A, Kleinmaier R, Brath U, Erdélyi M (2012) Symmetric halogen bonding is preferred in solution. J Am Chem Soc 134:5706

    Article  CAS  Google Scholar 

  27. Harris RK, Becker ED, Cabral de Menezes SM, Goodfellow R, Granger P (2001) NMR nomenclature. Nuclear spin properties and conventions for chemical shifts. Pure Appl Chem 73:1795

    Article  CAS  Google Scholar 

  28. Bryce DL, Widdifield CM, Chapman RP, Attrell RJ (2011) Chlorine, bromine, and iodine solid-state NMR. eMagRes. doi:10.1002/9780470034590.emrstm1214

    Google Scholar 

  29. Chapman RP, Widdifield CM, Bryce DL (2009) Solid-state NMR of quadrupolar halogen nuclei. Prog Nucl Magn Reson Spectrosc 55:215

    Article  CAS  Google Scholar 

  30. Widdifield CM, Chapman RP, Bryce DL (2009) Chlorine, bromine, and iodine solid-state NMR spectroscopy. Annu Rep Nucl Magn Reson Spectrosc 66:195

    CAS  Google Scholar 

  31. Grzesiek S, Cordier F, Jaravine V, Barfield M (2004) Insights into biomolecular hydrogen bonds from hydrogen bond scalar couplings. Prog Nucl Magn Reson Spectrosc 45:275

    Article  CAS  Google Scholar 

  32. Ledbetter MP, Saielli G, Bagno A, Tran N, Romalis MV (2012) Observation of scalar nuclear spin-spin coupling in van der Waals complexes. Proc Natl Acad Sci U S A 109:12393

    Article  CAS  Google Scholar 

  33. Del Bene JE, Alkorta I, Elguero J (2008) Spin-spin coupling across intermolecular F-Cl · · · N halogen bonds. J Phys Chem A 112:7925

    Article  Google Scholar 

  34. Del Bene JE, Alkorta I, Elguero J (2010) Ab initio study of ternary complexes A···NCH···C with A, C = HCN, HF, HCl, ClF, and LiH: energetics and spin-spin coupling constants across intermolecular bonds. J Phys Chem A 114:8463

    Article  Google Scholar 

  35. Alkorta I, Sanchez-Sanz G, Elguero J, Del Bene JE (2012) FCl:PCX complexes: old and new types of halogen bonds. J Phys Chem A 116:2300

    Article  CAS  Google Scholar 

  36. Vinogradov E, Madhu PK, Vega S (2005) Strategies for high-resolution proton spectroscopy in solid-state NMR. Top Curr Chem 246:33

    Article  CAS  Google Scholar 

  37. Lucken EAC (1969) Nuclear quadrupolar coupling constants. Academic, London

    Google Scholar 

  38. Viger-Gravel J, Korobkov I, Bryce DL (2011) Multinuclear solid-state magnetic resonance and X-ray diffraction study of some thiocyanate and selenocyanate complexes exhibiting halogen bonding. Cryst Growth Des 11:4984

    Article  CAS  Google Scholar 

  39. Viger-Gravel J, Leclerc S, Korobkov I, Bryce DL (2013) Correlation between 13C chemical shifts and the halogen bonding environment in a series of solid para-diiodotetrafluorobenzene complexes. CrystEngComm 15:3168

    Article  CAS  Google Scholar 

  40. Attrell RJ, Widdifield CM, Korobkov I, Bryce DL (2012) Weak halogen bonding in solid haloanilinium halides probed directly via chlorine-35, bromine-81, and iodine-127 NMR spectroscopy. Cryst Growth Des 12:1641

    Article  CAS  Google Scholar 

  41. Semin GK, Babushkina TA, Khrlakyan SP, Pervova EY, Shokina VV, Knunyants IL (1971) I127 NQR spectra of fluorinated α, ω-diiodoalkanes and complexes with amines. Theor Exp Chem 4:179

    Article  Google Scholar 

  42. Blackstock SC, Lorand JP, Kochi JK (1987) Charge-transfer interactions of amines with tetrahalomethanes. X-Ray crystal structures of the donor-acceptor complexes of quinuclidine and diazabicyclo[2.2.2]octane with carbon tetrabromide. J Org Chem 52:1451

    Article  CAS  Google Scholar 

  43. Bricklebank N, Godfrey SM, Mackie AG, McAuliffe CA, Pritchard RG, Kobryn PJ (1993) Diiodophosphoranes. Synthesis and structure in the solid state and in solution. J Chem Soc Dalton Trans 1993:101

    Article  Google Scholar 

  44. Dillon KB, Waddington TC (1971) Structures of some dihalotriphenylphosphorus(V) compounds. Nat Phys Sci 230:158

    Article  CAS  Google Scholar 

  45. Bouchmella K, Dutremez SG, Alonso B, Mauri F, Gervais C (2008) 1H, 13C, and 15N solid-state NMR studies of imidazole- and morpholine-based model compounds possessing halogen and hydrogen bonding capabilities. Cryst Growth Des 8:3941

    Article  CAS  Google Scholar 

  46. Weingarth M, Raouafi N, Jouvelet B, Duma L, Bodenhausen G, Boujlel K, Schöllhorn B, Tekely P (2008) Revealing molecular self-assembly and geometry of non-covalent halogen bonding by solid-state NMR spectroscopy. Chem Commun 5981

    Google Scholar 

  47. García MA, Cabildo P, Claramunt RM, Pinilla E, Torres MR, Alkorta I, Elguero J (2010) The interplay of hydrogen bonds and halogen bonds in the structure of NH-pyrazoles bearing C-aryl and C-halogen substituents. Inorg Chim Acta 363:1332

    Article  Google Scholar 

  48. Bertani R, Metrangolo P, Moiana A, Perez E, Pilati T, Resnati G, Rico-Lattes I, Sassi A (2002) Supramolecular route to fluorinated coatings: self-assembly between poly(4-vinylpyridines) and haloperfluorocarbons. Adv Mater 14:1197

    Article  CAS  Google Scholar 

  49. Nonappa, Lahtinen M, Kolehmainen E, Haarala J, Shevchenko A (2013) Evidence of weak halogen bonding: new insights in itraconazole and its succinic acid cocrystal. Cryst Growth Des 13:346

    Article  CAS  Google Scholar 

  50. Widdifield CM, Cavallo G, Facey GA, Pilati T, Lin J, Metrangolo P, Resnati G, Bryce DL (2013) Multinuclear solid-state magnetic resonance as a sensitive probe of structural changes upon the occurrence of halogen bonding in co-crystals. Chem Eur J 19:11949

    Article  CAS  Google Scholar 

  51. Baldrighi M, Cavallo G, Chierotti MR, Gobetto R, Metrangolo P, Pilati T, Resnati G, Terraneo G (2013) Halogen bonding and pharmaceutical cocrystals: the case of a widely used preservative. Mol Pharm 10:1760

    Article  CAS  Google Scholar 

  52. Lemouchi C, Vogelsberg CS, Zorina L, Simonov S, Batail P, Brown S, Garcia-Garibay MA (2011) Ultra-fast rotors for molecular machines and functional materials via halogen bonding: crystals of 1,4-bis(iodoethynyl)bicycle[2.2.2]octane with distinct gigahertz rotation at two sites. J Am Chem Soc 133:6371

    Article  CAS  Google Scholar 

  53. Cauliez P, Polo V, Roisnel T, Llusar R, Fourmigué M (2010) The thiocyanate anion as a polydentate halogen bond acceptor. CrystEngComm 12:558

    Article  CAS  Google Scholar 

  54. Gray L, Jones PG (2002) Secondary bonding interactions in some haloanilinium halides. Z Naturforsch 57b:61

    Google Scholar 

  55. Raatikainen K, Cametti M, Rissanen K (2010) The subtle balance of weak supramolecular interactions: the hierarchy of halogen and hydrogen bonds in haloanilinium and halopyridinium salts. Beilstein J Org Chem 6:4. doi:10.3762/bjoc.6.4

    Article  Google Scholar 

  56. Perras FA, Bryce DL (2012) Direct investigation of covalently bound chlorine in organic compounds by solid-state 35Cl NMR spectroscopy and exact spectral line-shape simulations. Angew Chem Int Ed 51:4227

    Article  CAS  Google Scholar 

  57. Bowmaker GA (1976) Nuclear quadrupole resonance of charge transfer complexes. Part 3.-A 14N and 35Cl N.Q.R. study of the 1:1 complex of 3,5-dichloropyridine with iodine monochloride. J Chem Soc Faraday Trans 2 72:1964

    Article  CAS  Google Scholar 

  58. Bowmaker GA, Hacobian S (1968) Nuclear quadrupole resonance of charge transfer complexes. I. The trihalide ions. Aust J Chem 21:551

    Article  CAS  Google Scholar 

  59. Bowmaker GA, Hacobian S (1969) Nuclear quadrupole resonance of charge-transfer complexes. II. The amine halogen complexes. Aust J Chem 22:2047

    Article  CAS  Google Scholar 

  60. Bowmaker GA, Boyd PDW (1987) An SCF-MS-Xα study of the bonding and nuclear quadrupole coupling in 1:1 complexes of amines with diatomic halogens and interhalogens. J Chem Soc Faraday Trans 2 83:2211

    Article  CAS  Google Scholar 

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Acknowledgements

We are grateful to the Natural Sciences and Engineering Research Council of Canada for supporting our research in this area. J. V.-G. thanks the “Fonds de recherche du Québec – Nature et technologies” for a graduate scholarship.

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Authors and Affiliations

  1. Department of Chemistry, University of Ottawa, Ottawa, ON, Canada

    David L. Bryce & Jasmine Viger-Gravel

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  1. David L. Bryce
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  2. Jasmine Viger-Gravel
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Correspondence to David L. Bryce .

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Editors and Affiliations

  1. Dipartimento di Chimica, Polytechnic University of Milan, Milano, Italy

    Pierangelo Metrangolo

  2. Dipartimento di Chimica, Polytechnic University of Milan, Milano, Italy

    Giuseppe Resnati

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Bryce, D.L., Viger-Gravel, J. (2014). Solid-State NMR Study of Halogen-Bonded Adducts. In: Metrangolo, P., Resnati, G. (eds) Halogen Bonding I. Topics in Current Chemistry, vol 358. Springer, Cham. https://doi.org/10.1007/128_2014_542

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