Halogen bonding in hypervalent iodine compounds

Topics in Current Chemistry

Volumn 373, Issue , 2016, Pages 289-310

  Catalano, Luca ^a   Cavallo, Gabriella ^a   Metrangolo, Pierangelo ^a   Resnati, Giuseppe ^a   Terraneo, Giancarlo ^a  

^a POLITECNICO DI MILANO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84976428001     PISSN: 03401022     EISSN: None     Source Type: Book Series    
DOI: 10.1007/128_2015_666     Document Type: Article

References (112)

1. Dohi T, Kita Y (2015) In: Kahio T (ed) Hypervalent iodine in iodine chemistry and applications. Wiley, Hoboken
2. Zhdankin VV (2013) Hypervalent iodine chemistry: preparation, structure, and synthetic applications of polyvalent iodine compounds. Wiley, Hoboken
3. Wirth T (2005) Hypervalent iodine in synthesis: scope and new directions. Angew Chem Int Ed 44:3656–3665
4. Wirth T (ed) (2003) Hypervalent iodine chemistry: modern developments in organic synthesis, Topics in current chemistry series 224. Springer, Berlin
5. Varvoglis A (1997) Hypervalent iodine in organic synthesis. Academic, London
6. Varvoglis A (1992) The organic chemistry of polycoordinated iodine. VCH, New York
7. Zhdankin VV, Stang PJ (2008) Chem Rev 108:5299–5358
8. Zhdankin VV, Maydanovych O, Herschbach J, Bruno J, Matveeva ED, Zefirov NS (2002) Tetrahedron Lett 43:2359–2361
9. Huang Z, Yu X, Huang X (2002) J Org Chem 67:8261–8264
10. Stang P, Zhdankin VV (1996) Chem Rev 96:1123–1178
11. Moriarty RM, Prakash I, Prakash O, Freeman WA (1984) J Am Chem Soc 106:6082–6084
12. Desiraju GR, Ho PS, Kloo L, Legon AC, Marquardt R, Metrangolo P, Politzer P, Resnati G, Rissanen K (2013) Pure Appl Chem 35:1711–1713
13. Metrangolo P, Neukirch H, Pilati T, Resnati G (2005) Acc Chem Res 38:386–395
14. Metrangolo P, Meyer F, Pilati T, Resnati G, Terraneo G (2008) Angew Chem Int Ed 47:6114–6127
15. Metrangolo P, Resnati G (2008) Science 321:918–919
16. Priimagi A, Cavallo G, Metrangolo P, Resnati G (2013) Acc Chem Res 46:2686–2695
17. Metrangolo P, Resnati G (eds) (2015) Halogen bonding vol I and vol II. Impact on materials chemistry and life sciences, Topics in current chemistry series 358. Springer, Switzerland
18. Clark T, Hennemann M, Murray JS, Politzer P (2007) J Mol Model 13:291–296
19. Politzer P, Lane P, Concha MC, Ma Y, Murray JS (2007) J Mol Model 13:305–311
20. Metrangolo P, Pilati T, Resnati G (2006) CrystEngComm 8:946–947
21. Nyburg SC, Szymansky JT (1968) Chem Commun 669–671
22. Nyburg SC, Faerman CH (1985) Acta Crystallogr B 41:274–279
23. Hathwar VR, Guru Row TN (2011) J Phys Chem A 114:13434–13441
24. Brezgunova ME, Aubert E, Dahaoui S, Fertey P, Lebégue S, Jelsch C, Angyàn JG, Espinosa E (2012) Cryst Growth Des 12:5273–5386
25. Hantzsch A (1915) Chem Ber 48:797–816
26. Nakamoto K, Margoshes M, Rundle RE (1955) J Am Chem Soc 77:6480–6486
27. Schleyer P (1959) J Am Chem Soc 81:3164–3165
28. Nelyubina YV, Antipin MY, Dunin DS, Kotov VY, Lyssenko KA (2010) Chem Commun 46:5325–5327
29. Colin JJ (1814) Ann Chim 91:252–272
30. Walsh R, Padgett CW, Metrangolo P, Resnati G, Hanks TW, Pennington WT (2001) Cryst Growth Des 1:165–175
31. Lommerse JPM, Stone AJ, Taylor R, Allen FH (1996) J Am Chem Soc 118:3108–3116
32. Metrangolo P, Resnati G, Pilati T, Biella S (2008) Struct Bond 126:105–136
33. Valerio G, Raos G, Meille SV, Metrangolo P, Resnati G (2000) J Phys Chem A 104:1617–1620
34. Aäckeroy CB, Baldrighi M, Desper J, Metrangolo P, Resnati G (2013) Chem Eur J 13:16240–16247
35. Aäckeroy CB, Wijethunga CK, Desper J (2014) J Mol Struct 1072:20–27
36. Le Questel JY, Laurence C, Graton J (2013) CrystEngComm 15:3212–3221
37. Kapecki JA, Baldwin JE (1969) J Am Chem Soc 91:1120–1123
38. Rosenfield RE Jr, Parthasarathy R, Dunitz JD (1977) J Am Chem Soc 99:4860–4862
39. Guru Row TN, Parthasarathy R (1981) J Am Chem Soc 103:477–479
40. Bleiholder C, Werz DB, Köppel H, Gleiter R (2006) J Am Chem Soc 128:2666–2674
41. Murray JS, Lane P, Clark T, Politzer P (2007) J Mol Med 13:1033–1038
42. Wang W, Ji B, Zhang YJ (2009) J Phys Chem A 113:8132–8135
43. Metrangolo P, Resnati G (2012) Nat Chem 4:437–438
44. Politzer P, Riley KE, Bulat FA, Murray JS (2012) Comput Theor Chem 998:2–8
45. Bauza A, Quiñonero D, Deya PM, Frontera A (2013) CrystEngComm 15:3137–3144
46. Hu NH, Liu W, Aoki K (2000) Bull Chem Soc Jpn 73:1043–1052
47. Murray JS, Lane P, Politzer P (2007) Int J Quantum Chem 107:2286–2292
48. Politzer P, Murray JS, Lane P (2007) Int J Quantum Chem 107:3046–3052
49. Zahn S, Frank R, Hey-Hawkins E, Kirchner B (2011) Chem Eur J 17:6034–6038
50. Li QZ, Li R, Liu XF, Li WZ, Cheng JB (2012) ChemPhysChem 13:1205–1212
51. Adhikari U, Scheiner S (2012) Chem Phys Lett 532:31–35
52. Scheiner S (2013) Acc Chem Res 46:280–288
53. Setiawan D, Krafka E, Cremer D (2015) J Phys Chem A 119:1642–1656
54. Nelyubina YV, Korlyukov AA, Lyssenko KA (2015) ChemPhysChem 16:676–681
55. Bauza´ A, Mooibroek TJ, Frontera A (2013) Angew Chem Int Ed 52:12317–12321
56. Politzer P, Murray JS, Clark T (2013) Phys Chem Chem Phys 15:11178–11189
57. Politzer P, Murray JS (2013) ChemPhysChem 14:278–294
58. Politzer P, Murray JS, Lane P, Concha MC (2009) Int J Quantum Chem 109:3773–3780
59. Murray JS, Lane P, Politzer P (2009) J Mol Model 15:723–729
60. Grabowski SJ (2014) Phys Chem Chem Phys 16:1824–1834
61. Merrit EA, Olofsson B (2009) Angew Chem Int Ed 48:9052–9070
62. Rissanen K, Haukka M(2015) Halonium ions as halogen bond donors in the solid state [XL2] Y complexes. Top Curr Chem 358:77–90
63. Politzer P, Murray JS, Metrangolo P, Resnati G. Manuscript in preparation
64. Alcock NW, Countyman RM (1977) J Chem Soc Dalton Trans 3:217–219
65. Khotsyanova TL, Babushkina TA, Saatsazov VV, Tolstaya TP, Lisichkina IN, Semin GK (1976) Koord Chim 2:1567
66. Alcock NW, Countryman RM (1977) J Chem Soc Dalton Trans 217–219
67. Bykowski D, McDonald R, Tykwinski RR (2003) ARKIVOC 4:21–29
68. Zhiying H, Yuanzhu C, Jiaxi L, Huaxue J (1982) Chin J Struct Chem 1:77–79
69. Hinkle RJ, McDonald R (2003) Acta Crystallogr C58:117–121
70. Murray SJ, Muller-Bünz H, Ibrahim H (2012) Chem Commun 48:6268–6270
71. Camps P, Gomez T, Lozano D, Calvet T, Font-Bardia M (2012) Molecules 17:8795–8803
72. Bailly F, Barthen P, Frohn HJ, Kockerling M (2000) Z Anorg Allg Chem 626:2419–2427
73. Frohn HJ, Wenda A, Flörke U (2008) Z Anorg Allg Chem 634:764–770
74. Frohn HJ, Wenda A, Flörke U (2010) Tetrahedron 66:5762–5767
75. Lubriks D, Sokolovs I, Suna E (2012) J Am Chem Soc 134:15436–15442
76. Suefuji T, Shiro M, Yamaguchi K, Ochiai M (2006) Heterocycles 67:391–397
77. DesMarteau DD, Pennigton WT, Montanari V, Thomas BH (2003) J Fluor Chem 122:57–61
78. Stang PJ, Chen K, Arif AM (1995) J Am Chem Soc 117:8793–8797
79. Wu G, Zheng PJ, Zhu SZ, Chen QY (1991) Acta Crystallogr C47:1227–1230
80. Ochiai M, Suefuji T, Miyamoto K, Tada N, Goto S, Shiro M, Sakamoto S, Yamaguchi K (2003) J Am Chem Soc 126:769–776
81. Williamson BL, Stang PJ, Arif AM (1993) J Am Chem Soc 115:2590–2597
82. Schafer S, Wirth T (2010) Angew Chem Int Ed 49:2786–2789
83. Dixon L, Carroll MA, Gregson TJ, Ellames GJ, Harrington RW, Clegg W (2013) Eur J Org Chem 12:2334–2345
84. Stang PJ, Arif AM, Crittell CM (1990) Angew Chem Int Ed 29:287–288
85. Justik MW, Protasiewicz JD, Updegraff JB (2009) Tetrahedron Lett 50:6072–6075
86. Brand JP, Chevalley C, Scepelliti R, Waser J (2012) Chem Eur J 18:5655–5666
87. Lubriks D, Sokolovs I, Suna E (2011) Org Lett 13:4324–4327
88. Zhdankin VV, Mayadanovych O, Herschbach J, McDonald R, Tykwinski RR (2002) J Am Chem Soc 124:11614–11615
89. Koser GF, McConville DB, Rabah GA, Youngs WJ (1995) J Chem Crystallogr 25:857–862
90. Ochiai M, Masaki Y, Shiro M (1991) J Org Chem 56:5511–5513
91. Eisenberger P, Gischig S, Togni A (2006) Chem Eur J 12:2579–2586
92. Niedermann K, Welch JM, Koller R, Cvengrosˆ J, Santschi N, Battaglia P, Togni A (2010) Tetrahedron 66:5753–5761
93. Yusubov MS, Yusubova RY, Nemykin VN, Zhdankin VV (2013) J Org Chem 78:3767–3773
94. Moss RA, Bracken K, Emge TJ (1995) J Org Chem 60:7739–7746
95. Kieltsch I, Eisenberger P, Togni A (2007) Angew Chem Int Ed 5:754–757
96. Niederman K, Welch JM, Koller R, Cvengroš J, Santschi N, Battaglia P, Togni A (2010) Tetrahedron 66:5753–5761
97. Blake AJ, Novak A, Davies M, Robinson RI, Woodward S (2009) Synth Commun 39:1065–1075
98. Eisenberg P, Gischig S, Togni A (2006) Chem Eur J 12:2579–2586
99. Zhdankin VV, Krasutsky AP, Kuehl CJ, Simonsen AJ, Woodward JK, Mismash B, Boltz JT (1996) J Am Chem Soc 118:5192–5197
100. Legault CY, Prévost J (2012) Acta Crystallogr E68:1238
101. Geary GC, Hope EG, Singh K, Stuart AM (2013) Chem Commun 49:9263–9265
102. Zhdankin VV, Khuel CJ, Arif AM, Stang PJ (1996) Mendeleev Commun 6:50–51
103. Frohn J, Hirschberg ME, Boese R, Blaser D, Florke U (2008) Z Anorg Allg Chem 634:2539–2550
104. Bess DB, Martin JC (1983) J Org Chem 48:4155–4156
105. Cui LQ, Dong ZL, Liu K, Zhang C (2011) Org Lett 13:6488–6491
106. Dess DB, Wilson SR, Martin JC (1993) J Am Chem Soc 115:2488–2495
107. Stevenson PJ, Treacy AB, Nieuwenhuyzen M (1997) J Chem Soc Perk Trans 2:589–592
108. O’Hair RAJ, Williams CM, Clark T (2010) J Mol Model 16:559–565
109. Wang W (2011) J Phys Chem A 115:9294–9299
110. Cheng N, Bi F, Liu Y, Zhang C, Liu C (2014) New J Chem 38:1256–1263
111. Moriarty RM, Vaid RK (1990) Synthesis 6:431–447
112. Stang PJ, Wingert H, Arif AM (1987) J Am Chem Soc 109:7235–7236