Erratum: Multiple Multidentate Halogen Bonding in Solution, in the Solid State, and in the (Calculated) Gas Phase (Chemistry - A European Journal (2015) 21 DOI: 10.1002/chem.201502043);Multiple Multidentate Halogen Bonding in Solution, in the Solid State, and in the (Calculated) Gas Phase

Chemistry - A European Journal

Volumn 21, Issue 39, 2015, Pages 13625-13636

  Jungbauer, Stefan H ^a,b   Schindler, Severin ^a,b   Herdtweck, Eberhardt ^b   Keller, Sandro ^c   Huber, Stefan M ^a,b  

^a RUHR UNIVERSITY BOCHUM   (Germany)

^b TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^c University of Koblenz Landau   (Germany)

Author keywords

anions; halogen compounds; molecular recognition; noncovalent interactions; thermodynamics

Indexed keywords

BINDING ENERGY; BINDING SITES; CALORIMETERS; CALORIMETRY; CHLORINE COMPOUNDS; DENSITY FUNCTIONAL THEORY; DENSITY OF GASES; HALOGEN COMPOUNDS; ISOTHERMS; MOLECULAR RECOGNITION; NEGATIVE IONS; SOLID SOLUTIONS; THERMODYNAMICS; TITRATION; X RAY ANALYSIS; X RAY CRYSTALLOGRAPHY; X RAYS;

BINDING PROPERTIES; CRYSTALLOGRAPHIC DATA; GAS-PHASE COMPLEXES; ISOTHERMAL TITRATION CALORIMETRY; NON-COVALENT INTERACTION; SOLID-STATE STRUCTURES; TETRAALKYLAMMONIUM; X RAY STRUCTURAL ANALYSIS;

GASES;

EID: 84941598939     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201503723     Document Type: Erratum

References (110)

1. Halogen Bonding: Fundamentals and Applications; P. Metrangolo, G. Resnati, Eds.; Springer: Berlin, 2008; Selected recent reviews:
2. P. Metrangolo, H. Neukirch, T. Pilati, G. Resnati, Acc. Chem. Res. 2005, 38, 386-395;
3. P. Metrangolo, F. Meyer, T. Pilati, G. Resnati, G. Terraneo, Angew. Chem. Int. Ed. 2008, 47, 6114-6127;
4. Angew. Chem. 2008, 120, 6206-6220;
5. M. Fourmigué, Curr. Opin. Solid State Mater. Sci. 2009, 13, 36-45;
6. A. C. Legon, Phys. Chem. Chem. Phys. 2010, 12, 7736-7747;
7. G. Cavallo, P. Metrangolo, T. Pilati, G. Resnati, M. Sansotera, G. Terraneo, Chem. Soc. Rev. 2010, 39, 3772-3783.
8. A. C. Legon, Angew. Chem. Int. Ed. 1999, 38, 2686-2714;
9. Angew. Chem. 1999, 111, 2850-2880.
10. M. Erdélyi, Chem. Soc. Rev. 2012, 41, 3547-3557;
11. T. M. Beale, M. G. Chudzinski, M. G. Sarwar, M. S. Taylor, Chem. Soc. Rev. 2013, 42, 1667-1680.
12. K. Rissanen, CrystEngComm 2008, 10, 1107-1113;
13. L. Brammer, G. M. Espallargas, S. Libri, CrystEngComm 2008, 10, 1712-1727;
14. R. Bertani, P. Sgarbossa, A. Venzo, F. Lelj, M. Amati, G. Resnati, T. Pilati, P. Metrangolo, G. Terraneo, Coord. Chem. Rev. 2010, 254, 677-695.
15. A. Karpfen, Struct. Bonding (Berlin) 2008, 126, 1-15;
16. L. P. Wolters, P. Schyman, M. J. Pavan, W. L. Jorgensen, F. M. Bickelhaupt, S. Kozuch, WIREs Comput. Mol. Sci. 2014, 4, 523-540; Selected publications:
17. P. Politzer, J. S. Murray, M. C. Concha, J. Mol. Model. 2007, 13, 643-650;
18. M. G. Chudzinski, M. S. Taylor, J. Org. Chem. 2012, 77, 3483-3491;
19. S. M. Huber, E. Jiminez-Izal, J. M. Ugalde, I. Infante, Chem. Commun. 2012, 48, 7708-7710;
20. S. M. Huber, J. D. Scanlon, E. Jiminez-Izal, J. M. Ugalde, I. Infante, Phys. Chem. Chem. Phys. 2013, 15, 10350-10357.
21. H. M. Yamamoto, J.-I. Yamaura, R. Kato, J. Am. Chem. Soc. 1998, 120, 5905-5913;
22. M. Fourmigué, P. Batail, Chem. Rev. 2004, 104, 5379;
23. H. L. Nguyen, P. N. Horton, M. B. Hursthouse, A. C. Legon, D. W. Bruce, J. Am. Chem. Soc. 2004, 126, 16-17;
24. D. W. Bruce, P. Metrangolo, F. Meyer, T. Pilati, C. Praesang, G. Resnati, G. Terraneo, S. G. Wainright, A. C. Whitwood, Chem. Eur. J. 2010, 16, 9511-9524;
25. R. W. Troff, T. Mäkelä, F. Topic, A. Valkonen, K. Raatikainen, K. Rissanen, Eur. J. Org. Chem. 2013, 1617-1637;
26. A. Mukherjee, S. Tothadi, G. R. Desiraju, Acc. Chem. Res. 2014, 47, 2514-2524.
27. P. Metrangolo, W. Panzeri, F. Recupero, G. Resnati, J. Fluorine Chem. 2002, 114, 27-33;
28. S. Libri, N. A. Jasim, R. N. Perutz, L. Brammer, J. Am. Chem. Soc. 2008, 130, 7842-7844;
29. M. G. Sarwar, B. Dragisic, L. J. Salsberg, C. Gouliaras, M. S. Taylor, J. Am. Chem. Soc. 2010, 132, 1646-1653;
30. C. Laurence, J. Graton, M. Berthelot, M. J. ElGhomari, Chem. Eur. J. 2011, 17, 10431-10444;
31. L. A. Hardegger, B. Kuhn, B. Spinnler, L. Anselm, R. Ecabert, M. Stihle, B. Gsell, R. Thoma, J. Diez, J. Benz, J.-M. Plancher, G. Hartmann, D. W. Banner, W. Haap, F. Diederich, Angew. Chem. Int. Ed. 2011, 50, 314-318;
32. Angew. Chem. 2011, 123, 329-334;
33. M. Cametti, K. Raatikainen, P. Metrangolo, T. Pilati, G. Terraneo, G. Resnati, Org. Biomol. Chem. 2012, 10, 1329-1333;
34. S. M. Walter, F. Kniep, L. Rout, F. P. Schmidtchen, E. Herdtweck, S. M. Huber, J. Am. Chem. Soc. 2012, 134, 8507-8512;
35. A.-C. C. Carlsson, J. Gräfenstein, A. Budnjo, J. L. Laurila, J. Bergquist, A. Karim, R. Kleinmeier, U. Brath, M. Erdelyi, J. Am. Chem. Soc. 2012, 134, 5706-5715;
36. M. G. Sarwar, B. Dragisic, E. Dimitrijevic, M. S. Taylor, Chem. Eur. J. 2013, 19, 2050-2058;
37. A.-C. C. Carlsson, A. Uhrbom, A. Karim, U. Brath, J. Gräfenstein, M. Erdelyi, CrystEngComm 2013, 15, 3087-3092;
38. O. Dumele, D. Wu, N. Trapp, N. Goroff, F. Diederich, Org. Lett. 2014, 16, 4722-4725;
39. M. Bedin, A. Karim, M. Reitti, A.-C.C. Carlsson, F. Topic, M. Cetina, F. Pan, V. Havel, F. Al-Ameri, V. Sindelar, K. Rissanen, J. Gräfenstein, M. Erdelyi, Chem. Sci. 2015, DOI:10.1039/C5SC01053E.
40. A. Mele, P. Metrangolo, H. Neukirch, T. Pilati, G. Resnati, J. Am. Chem. Soc. 2005, 127, 14972-14973;
41. C. J. Serpell, N. L. Kilah, P. J. Costa, V. Félix, P. D. Beer, Angew. Chem. Int. Ed. 2010, 49, 5322-5326;
42. Angew. Chem. 2010, 122, 5450-5454;
43. N. L. Kilah, M. D. Wise, C. J. Serpell, A. L. Thompson, N. G. White, K. E. Christensen, P. D. Beer, J. Am. Chem. Soc. 2010, 132, 11893-11895;
44. M. G. Sarwar, B. Dragisic, S. Sagoo, M. S. Taylor, Angew. Chem. Int. Ed. 2010, 49, 1674-1677;
45. Angew. Chem. 2010, 122, 1718-1721;
46. E. Dimitrijevic, P. Kvak, M. S. Taylor, Chem. Commun. 2010, 46, 9025-9027;
47. A. Caballero, N. G. White, P. D. Beer, Angew. Chem. Int. Ed. 2011, 50, 1845-1848;
48. Angew. Chem. 2011, 123, 1885-1888;
49. A. Caballero, F. Zapata, N. G. White, P. J. Costa, V. Félix, P. D. Beer, Angew. Chem. Int. Ed. 2012, 51, 1876-1880;
50. Angew. Chem. 2012, 124, 1912-1916;
51. F. Zapata, A. Caballero, N. G. White, T. D. W. Claridge, P. J. Costa, V. Félix, P. D. Beer, J. Am. Chem. Soc. 2012, 134, 11533-11541;
52. E. A. L. Gillis, M. Demireva, M. G. Sarwar, M. G.; Chudzinsky, M. S. Taylor, E. R. Williams, T. D. Fridgen, Phys. Chem. Chem. Phys. 2013, 15, 7638-7647;
53. Chudzinsky, M. S. Taylor, E. R. Williams, T. D. Fridgen, Phys. Chem. Chem. Phys. 2013, 15, 7638-7647;
54. K. Raatikainen, G. Cavallo, P. Metrangolo, G. Resnati, K. Rissanen, G. Terraneo, Cryst. Growth Des. 2013, 13, 871-877;
55. L. C. Gilday, P. D. Beer, Chem. Eur. J. 2014, 20, 8379-8385;
56. B. R. Mullaney, A. L. Thompson, P. D. Beer, Angew. Chem. Int. Ed. 2014, 53, 11458-11462;
57. Angew. Chem. 2014, 126, 11642-11646;
58. A. Caballero, L. Swan, F. Zapata, P. D. Beer, Angew. Chem. Int. Ed. 2014, 53, 11854-11858;
59. Angew. Chem. 2014, 126, 12048-12052;
60. M. J. Langton, S. W. Robinson, I. Marques, V. Félix, P. D. Beer, Nat. Chem. 2014, 6, 1039-1043;
61. A. Karim, M. Reitti, A.-C. C. Carlsson, J. Graefenstein, M. Erdelyi, Chem. Sci. 2014, 5, 3226-3233;
62. S. W. Robinson, C. L. Mustoe, N. G. White, A. Brown, A. L. Thompson, P. Kennepohl, P. D. Beer, J. Am. Chem. Soc. 2015, 137, 499-507.
63. A. VargasJentzsch, D. Emery, J. Mareda, P. Metrangolo, G. Resnati, S. Matile, Angew. Chem. Int. Ed. 2011, 50, 11675-11678;
64. Angew. Chem. 2011, 123, 11879-11882;
65. A. VargasJentzsch, D. Emery, J. Mareda, S. K. Nayak, P. Metrangolo, G. Resnati, N. Sakai, S. Matile, Nat. Commun. 2012, 3, 905-913;
66. A. VargasJentzsch, S. Matile, J. Am. Chem. Soc. 2013, 135, 5302-5303;
67. A. VargasJentzsch, A. Henning, J. Mareda, S. Matile, Acc. Chem. Res. 2013, 46, 2791-2800;
68. A. VargasJentzsch, S. Matile, Top. Curr. Chem. 2014, 358, 205-239.
69. A. Bruckmann, M. A. Pena, C. Bolm, Synlett 2008, 6, 900-902;
70. S. M. Walter, F. Kniep, E. Herdtweck, S. M. Huber, Angew. Chem. Int. Ed. 2011, 50, 7187-7191;
71. Angew. Chem. 2011, 123, 7325-7329;
72. F. Kniep, S. H. Jungbauer, Q. Zhang, S. M. Walter, S. Schindler, I. Schnapperelle, E. Herdtweck, S. M. Huber, Angew. Chem. Int. Ed. 2013, 52, 7028-7032;
73. Angew. Chem. 2013, 125, 7166-7170;
74. S. H. Jungbauer, S. M. Walter, S. Schindler, L. Rout, F. Kniep, S. M. Huber, Chem. Commun. 2014, 50, 6281-6284;
75. W. He, Y.-C. Ge, C.-H. Tan, Org. Lett. 2014, 16, 3244-3247;
76. Y. Takeda, D. Hisakuni, C.-H. Lin, S. Minakata, Org. Lett. 2015, 17, 318-321.
77. K. Hervé, O. Cador, S. Golhen, K. Costuas, J.-F. Halet, S. Shirahata, T. Muto, T. Imakubo, A. Miyazaki, L. Ouahab, Chem. Mater. 2006, 18, 790-797;
78. C. B. Aakeröy, A. Rajbanshi, P. Metrangolo, G. Resnati, M. F. Parisi, J. Desper, T. Pilati, CrystEngComm 2012, 14, 6366-6368;
79. D. Cao, M. Hong, A. K. Blackburn, Z. Liu, J. M. Holcroft, J. F. Stoddart, Chem. Sci. 2014, 5, 4242-4248;
80. S. H. Jungbauer, D. Bulfield, F. Kniep, C. W. Lehmann, E. Herdtweck, S. M. Huber, J. Am. Chem. Soc. 2014, 136, 16740-16743;
81. A. Linke, S. H. Jungbauer, S. M. Huber, S. R. Waldvogel, Chem. Commun. 2015, 51, 2040-2043.
82. Z. Yoshida, Y. Tawara, J. Am. Chem. Soc. 1971, 93, 2573-2574;
83. R. Weiss, T. Brenner, F. Hampel, A. Wolski, Angew. Chem. 1995, 107, 481-483.
84. S. H. Jungbauer, S. Schindler, F. Kniep, S. M. Walter, L. Rout, S. M. Huber, Synlett 2013, 24, 2624-2628.
85. S. M. Walter, S. H. Jungbauer, F. Kniep, S. Schindler, E. Herdtweck, S. M. Huber, J. Fluorine Chem. 2013, 150, 14-20.
86. A. J. Bondi, Phys. Chem. 1964, 68, 441-451.
87. Adduct p-1 Cl has already been published; see Ref.[10c]; CCDC 924128 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre.
88. O. Hassel, Q. Romming, Rev. Chem. Soc 1962, 16, 1-18;
89. H. A. Bent, Chem. Rev. 1968, 68, 587-648;
90. O. Hassel, Angew. Chem. 1970, 82, 821-827;
91. A. E. Reed, F. Weihold, R. Weiss, J. Macheleid, Phys. Chem. 1985, 89, 2688-2694;
92. R. Weiss, M. Rechinger, F. Hampel, Angew. Chem. Int. Ed. Engl. 1994, 33, 893-895;
93. Angew. Chem. 1994, 106, 901-903;
94. J. P. M. Lommerse, A. J. Stone, R. Taylor, F. H. Allen, J. Am. Chem. Soc. 1996, 118, 3108-3131;
95. A. Karpfen, Theor. Chem. Acc. 2003, 110, 1-9;
96. C. Wang, D. Danovich, Y. Mo, S. J. Shaik, J. Chem. Theory Comput. 2014, 10, 3726-3737.
97. S. Keller, C. Vargas, H. Zhao, G. Piszczek, C. A. Brautigam, P. Schuck, Anal. Chem. 2012, 84, 5066-5073.
98. J. C. D. Houtman, P. H. Brown, B. Bowden, H. Yamaguchi, E. Appella, L. E. Samelson, P. Schuck, Protein Sci. 2007, 16, 30-42.
99. G. Krainer, J. Broecker, C. Vargas, J. Fanghänel, S. Keller, Anal. Chem. 2012, 84, 10715-10722;
100. G. Krainer, S. Keller, Methods 2015, 76, 116-123.
101. K. A. Connors, A. Paulson, D. J. Toleda-Velasquez, J. Org. Chem. 1988, 53, 2023-2026;
102. P. Thordarson, Chem. Soc. Rev. 2011, 40, 1305-1322.
103. J. Broecker, C. Vargas, S. Keller, Anal. Biochem. 2011, 418, 307-309;
104. C. C. Robertson, R. N. Perutz, L. Brammer, C. A. Hunter, Chem. Sci. 2014, 5, 4179-4183.
105. Y. Lu, H. Li, X. Zhu, W. Zhu, H. Liu, J. Phys. Chem. A 2011, 115, 4667-4475.
106. C. Reichardt, Chem. Soc. Rev. 1994, 94, 2319-2358.
107. S. Grimme, J. Comput. Chem. 2006, 27, 1787-1799;
108. S. Grimme, S. Ehrlich, L. Goerigk, J. Comput. Chem. 2011, 32, 1456-1465.
109. F. Weigend, R. Ahlrichs, Phys. Chem. Chem. Phys. 2005, 7, 3297-3305.
110. C.Y. Legault, CYLview, 1.0b, Université deSherbrooke, 2009, http://www.cylview.org.