Halogen bond symmetry: the N–X–N bond

Journal of Physical Organic Chemistry

Volumn 28, Issue 3, 2015, Pages 226-233

  Hakkert, Sebastiaan B ^a   Erdélyi, Máté ^a  

^a UNIVERSITY OF GOTHENBURG   (Sweden)

Author keywords

halogen bond; halonium ion; hydrogen bond; short bond; symmetry

Indexed keywords

COPYRIGHTS; ELECTRONIC STRUCTURE; ELECTROSTATICS; GEOMETRY; IONS; CRYSTAL SYMMETRY; HYDROGEN BONDS;

ATTRACTIVE INTERACTIONS; ELECTRON DEFICIENCY; ENERGY; HALOGEN BONDING; HALOGEN BONDS; HALONIA ION; HALONIUM; POSITIVE CHARGES; SHORT BOND; SYMMETRY; CHARGE DELOCALIZATION; ELECTROSTATIC CONTRIBUTIONS; EXPERIMENTAL CONFIRMATION; PRACTICAL IMPORTANCE; STRUCTURE AND PROPERTIES;

HYDROGEN BONDS; CHLORINE;

EID: 85027920806     PISSN: 08943230     EISSN: 10991395     Source Type: Journal    
DOI: 10.1002/poc.3325     Document Type: Review

References (113)

1. Arunan, E., Desiraju, G.R., Klein, R.A., Sadlej, J., Scheiner, S., Alkorta, I., Clary, D.C., Crabtree, R.H., Dannenberg, J.J., Hobza, P., Kjaergaard, H.G., Legon, A.C., Mennucci, B., Nesbitt, D.J., Pure Appl. Chem., 83, 2011, 1637.
2. Moore, T.S., Winmill, T.F., J. Chem. Soc., 101, 1912, 1635.
3. Meot‐Ner (Mautner), M., Chem. Rev., 112, 2012, PR22.
4. Grabowski, S.J., Hydrogen Bonding—New Insights, 2006, Springer, Dordrecht, the Netherlands.
5. Kojic‐Prodic, B., Molcanov, K., Acta Chim. Slov., 55, 2008, 692.
6. Metrangolo, P., Neukirch, H., Pilati, T., Resnati, G., Acc. Chem. Res., 38, 2005, 386.
7. Guthrie, F., J. Chem. Soc., 16, 1863, 239.
8. Metrangolo, P., Resnati, G., Science, 321, 2008, 918.
9. Metrangolo, P., Resnati, G., Chem. Eur. J., 7, 2001, 2511.
10. Desiraju, G.R., Parthasarathy, R., J. Am. Chem. Soc., 111, 1989, 8725.
11. Scholfield, M.R., Vander Zanden, C.M., Carter, M., Ho, P.S., Protein Sci., 22, 2013, 139.
12. Auffinger, P., Hays, F.A., Westhof, E., Ho, P.S., Proc. Natl. Acad. Sci. U. S. A., 101, 2004, 16789.
13. Svensson, P.H., Kloo, L., Inorg. Chem., 38, 1999, 3390.
14. Legon, A.C., Angew. Chem. Int. Ed., 38, 1999, 2686.
15. Legon, A.C., Phys. Chem. Chem. Phys., 12, 2010, 7736.
16. Russo, L., Biella, S., Lahtinen, M., Liantonio, R., Metrangolo, P., Resnati, G., Rissanen, K., Cryst. Eng. Comm., 9, 2007, 341.
17. Troff, R.W., Makela, T., Topic, F., Valkonen, A., Raatikainen, K., Rissanen, K., Eur. J. Org. Chem., 2013, 1617.
18. Sarwar, M.G., Dragisic, B., Salsberg, L.J., Gouliaras, C., Taylor, M.S., J. Am. Chem. Soc., 132, 2010, 1646.
19. Beale, T.M., Chudzinski, M.G., Sarwar, M.G., Taylor, M.S., Chem. Soc. Rev., 42, 2013, 1667.
20. Politzer, P., Murray, J.S., Chem. Phys. Chem., 14, 2013, 278.
21. Clark, T., Hennemann, M., Murray, J.S., Politzer, P., J. Mol. Model., 13, 2007, 291.
22. Desiraju, G.R., Ho, P.S., Kloo, L., Legon, A.C., Marquardt, R., Metrangolo, P., Politzer, P., Resnati, G., Rissanen, K., Pure Appl. Chem., 85, 2013, 1711.
23. Zhao, N., Hastings, G., J. Phys. Chem. B, 117, 2013, 8705.
24. Umeyama, H., Morokuma, K., J. Am. Chem. Soc., 99, 1977, 1316.
25. Grabowski, S.J., Phys. Chem. Chem. Phys., 15, 2013, 7249.
26. Syzgantseva, O.A., Tognetti, V., Joubert, L., J. Phys. Chem. A, 117, 2013, 8969.
27. Buckingham, A.D., Del Bene, J.E., McDowell, S.A.C., Chem. Phys. Lett., 463, 2008, 1.
28. Wolters, L.P., Bickelhaupt, F.M., Chem. Open, 1, 2012, 96.
29. Grabowski, S.J., Chem. Rev., 111, 2011, 2597.
30. Carlsson, A.‐C.C., Gräfenstein, J., Budnjo, A., Laurila, J.L., Bergquist, J., Karim, A., Kleinmaier, R., Brath, U., Erdelyi, M., J. Am. Chem. Soc., 134, 2012, 5706.
31. An, X., Jing, B., Li, Q., J. Phys. Chem. A, 114, 2010, 6438.
32. Lu, Y.X., Li, H.Y., Zhu, X., Liu, H.L., Zhu, W.L., Int. J. Quant. Chem., 112, 2012, 1421.
33. Gilli, P., Bertolasi, V., Ferretti, V., Gilli, G., J. Am. Chem. Soc., 116, 1994, 909.
34. Perrin, C.L., Pure Appl. Chem., 81, 2009, 571.
35. Saenger, J.G.A., Hydrogen bonding in biological structures, 1991, Springer, Berlin.
36. Perrin, C.L., Nielson, J.B., Annu. Rev. Phys. Chem., 48, 1997, 511.
37. Glidewell, C., Holden, H.D., Acta Crystallogr. B, 38, 1982, 667.
38. Perrin, C.L., Science, 266, 1994, 1665.
39. Perrin, C.L., Acc. Chem. Res., 43, 2010, 1550.
40. Limbach, H.H., Denisov, G.S., Golubev, N.S., Chapter 7. Hydrogen Bond Isotope Effects Studied by NMR, 2006, Taylor and Francis, New York.
41. Bogle, X.S., Singleton, D.A., J. Am. Chem. Soc., 133, 2011, 17172.
42. Georgiou, D.C., Butler, P., Browne, E.C., Wilson, D.J.D., Dutton, J.L., Aust. J. Chem., 66, 2013, 1179.
43. Perkins, C.W., Martin, J.C., Arduengo, A.J., Lau, W., Alegria, A., Kochi, J.K., J. Am. Chem. Soc., 102, 1980, 7753.
44. Ginn, S.G.W., Wood, J.L., T. Faraday Soc., 62, 1966, 777.
45. Carlsson, A.‐C.C., Gräfenstein, J., Laurila, J.L., Bergquist, J., Erdelyi, M., Chem. Commun., 48, 2012, 1458.
46. Landrum, G.A., Goldberg, N., Hoffmann, R., J. Chem. Soc. Dalton, 1997, 3605.
47. Munzarova, M.L., Hoffmann, R., J. Am. Chem. Soc., 124, 2002, 4787.
48. Braida, B., Hiberty, P.C., J. Am. Chem. Soc., 126, 2004, 14890.
49. Carlsson, A.‐C.C., Uhrbom, M., Karim, A., Brath, U., Gräfenstein, J., Erdelyi, M., CrystEngComm, 15, 2013, 3087.
50. Pimentel, G.C., J. Chem. Phys., 19, 1951, 446.
51. Alvarez‐Rua, C., Garcia‐Granda, S., Ballesteros, A., Gonzalez‐Bobes, F., Gonzalez, J.M., Acta Crystallogr. E, 58, 2002, O1381.
52. Hassel, O., Hope, H., Acta Chem. Scand., 15, 1961, 407.
53. Okitsu, T., Yumitate, S., Sato, K., In, Y., Wada, A., Chem. Eur. J., 19, 2013, 4992.
54. Batsanov, A.S., Lightfoot, A.P., Twiddle, S.J.R., Whiting, A., Acta Crystallogr. E, 62, 2006, O901.
55. Batsanov, A.S., Howard, J.A.K., Lightfoot, A.P., Twiddle, S.J.R., Whiting, A., Eur. J. Org. Chem., 2005, 1876.
56. Brayer, G.D., James, M.N.G., Acta Crystallogr. B, 38, 1982, 654.
57. Neverov, A.A., Feng, H.X.M., Hamilton, K., Brown, R.S., J. Org. Chem., 68, 2003, 3802.
58. Alcock, N.W., Robertson, G.B., J. Chem. Soc. Dalton, 1975, 2483.
59. Blair, L.K., Parris, K.D., Hii, P.S., Brock, C.P., J. Am. Chem. Soc., 105, 1983, 3649.
60. Brock, C.P., Fu, Y.G., Blair, L.K., Chen, P., Lovell, M., Acta Crystallogr. C, 44, 1988, 1582.
61. Pritzkow, H., Acta Crystallogr. B, 31, 1975, 1505.
62. Elding, M., Albertsson, J., Svensson, G., Eberson, L., Acta Chem. Scand., 44, 1990, 135.
63. Crawford, M.J., Gobel, M., Karaghiosoff, K., Klapotke, T.M., Welch, J.M., Inorg. Chem., 48, 2009, 9983.
64. Muller, U., Dubgen, R., Dehnicke, K., Z. Anorg. Allg. Chem., 463, 1980, 7.
65. Mootz, D., Boenigk, D., Z. Anorg. Allg. Chem., 544, 1987, 159.
66. Helmholz, L., Rogers, M.T., J. Am. Chem. Soc., 61, 1939, 2950.
67. Emsley, J., Chem. Soc. Rev., 9, 1980, 91.
68. Bakshi, P.K., James, M.A., Cameron, T.S., Knop, O., Can. J. Chem., 74, 1996, 559.
69. Robertson, K.N., Cameron, T.S., Knop, O., Can. J. Chem., 74, 1996, 1572.
70. Almlof, J., Ottersen, T., Acta Crystallogr. A, 35, 1979, 137.
71. Madsen, A.O., Struct. Bond., 146, 2012, 21.
72. Claramunt, R.M., Perez‐Torralba, M., Maria, D.S., Sanz, D., Elena, B., Alkorta, I., Elguero, J., J. Magn. Reson., 206, 2010, 274.
73. Alkorta, I., Blanco, F., Elguero, J., Cent. Eur. J. Chem., 7, 2009, 683.
74. Kong, S., Borissova, A.O., Lesnichin, S.B., Hartl, M., Daemen, L.L., Eckert, J., Antipin, M.Y., Shenderovich, I.G., J. Phys. Chem. A, 115, 2011, 8041.
75. Villarrealsalinas, B.E., Schlemper, E.O., J. Cryst. Mol. Struct., 8, 1978, 217.
76. Mautner, F.A., Goher, M.A.S., Polyhedron, 18, 1999, 553.
77. Kobayashi, N., Naito, T., Inabe, T., Bull. Chem. Soc. Jpn., 76, 2003, 1351.
78. Yutronic, N., Merchan, J., Gonzalez, G., Garland, M.T., J. Chem. Soc. Perkin Trans., 2, 1956, 2002.
79. Haque, I., Wood, J.L., J. Mol. Struct., 2, 1968, 217.
80. Saunders, M., Telkowski, L., Kates, M.R., J. Am. Chem. Soc., 99, 1977, 8070.
81. Siehl, H.U., Adv. Phys. Org. Chem., 23, 1987, 63.
82. Perrin, C.L., Karri, P., Moore, C., Rheingold, A.L., J. Am. Chem. Soc., 134, 2012, 7766.
83. Perrin, C.L., Lau, J.S., J. Am. Chem. Soc., 128, 2006, 11820.
84. Perrin, C.L., Lau, J.S., Kim, Y.J., Karri, P., Moore, C., Rheingold, A.L., J. Am. Chem. Soc., 131, 2009, 13548.
85. Perrin, C.L., Ohta, B.K., J. Am. Chem. Soc., 123, 2001, 6520.
86. Perrin, C.L., Ohta, B.K., Bioorg. Chem., 30, 2002, 3.
87. Guo, J., Tolstoy, P.M., Koeppe, B., Golubev, N.S., Denisov, G.S., Smirnov, S.N., Limbach, H.H., J. Phys. Chem. A, 116, 2012, 11180.
88. Smirnov, S.N., Benedict, H., Golubev, N.S., Denisov, G.S., Kreevoy, M.M., Schowen, R.L., Limbach, H.H., Can. J. Chem., 77, 1999, 943.
89. Shenderovich, I.G., Burtsev, A.P., Denisov, G.S., Golubev, N.S., Limbach, H.H., Magn. Reson. Chem., 39, 2001, S91.
90. Perrin, C.L., Burke, K.D., J. Am. Chem. Soc., 136, 2014, 4355.
91. Sokolov, N.D., Vener, M.V., Savelev, V.A., J. Mol. Struct., 222, 1990, 365.
92. Tayyari, S.F., Mandizadeh, S.J., Holakoei, S., Wang, Y.A., J. Mol. Struct., 971, 2010, 39.
93. Castro‐Fernandez, S., Lahoz, I.R., Llamas‐Saiz, A.L., Alonso‐Gomez, J.L., Cid, M.M., Navarro‐Vazquez, A., Org. Lett., 16, 2014, 1136.
94. Rubenacker, G.V., Brown, T.L., Inorg. Chem., 19, 1980, 398.
95. Pietrzak, M., Wehling, J.P., Kong, S., Tolstoy, P.M., Shenderovich, I.G., Lopez, C., Claramunt, R.M., Elguero, J., Denisov, G.S., Limbach, H.H., Chem. Eur. J., 16, 2010, 1679.
96. Zhang, F.S., Lynden‐Bell, R.M., Phys. Rev. Lett., 2003, 90.
97. Johnson, A.E., Myers, A.B., J. Phys. Chem., 100, 1996, 7778.
98. Margulis, C.J., Coker, D.F., Lynden‐Bell, R.M., Chem. Phys. Lett., 341, 2001, 557.
99. Sabin, R.J., Int. J. Quant. Chem., 2, 1968, 23.
100. Sabin, J.R., J. Mol. Struct., 7, 1971, 407.
101. Sabin, J.R., J. Mol. Struct., 11, 1972, 33.
102. Politzer, P., Murray, J.S., Clark, T., Phys. Chem. Chem. Phys., 15, 2013, 11178.
103. Lin, G.H.Y., Hope, H., Acta Crystallogr. B, B 28, 1972, 643.
104. Kozuch, S., Martin, J.M.L., J. Chem. Theor. Comput., 9, 2013, 1918.
105. Parra, R.D., Comput. Theor. Chem., 998, 2012, 183.
106. Parra, R.D., Molecules, 19, 2014, 1069.
107. Barluenga, J., Pure Appl. Chem., 71, 1999, 431.
108. Brown, R.S., Neverov, A.A., Liu, C.T., Maxwell, C.I., ACS Symp. Ser., 965, 2007, 458.
109. Politzer, P., Murray, J.S., CrystEngComm., 15, 2013, 3145.
110. Legon, A.C., Angew. Chem. Int. Ed., 38, 1999, 2687.
111. Stephens, S.L., Walker, N.R., Legon, A.C., Phys. Chem. Chem. Phys., 13, 2011, 20736.
112. Legon, A.C., Struct. Bond., 126, 2008, 17.
113. Fireston, R.A., J. Org. Chem., 36, 1971, 702.