Macrocyclic diorganotin complexes of γ-amino acid dithiocarbamates as hosts for ion-pair recognition

Inorganic Chemistry

Volumn 47, Issue 21, 2008, Pages 9874-9885

  Cruz Huerta, Jorge ^a   Carillo Morales, Manuel ^a   Santacruz Juárez, Ericka ^a   Hernández Ahuactzi, Irán F ^a   Escalante García, Jaime ^a   Godoy Alcantar, Carolina ^a   Guerrero Alvarez, Jorge A ^a   Höpfl, Herbert ^a   Morales Rojas, Hugo ^a   Sánchez, Mario ^b  

^a CENTRO DE INVESTIGACIONES QUÍMICAS   (Mexico)

^b UNIVERSITY OF GUANAJUATO   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; ANION; CATION; DI-N-BUTYLTIN; DIBUTYLTIN; DIPHENYLTIN; LIGAND; MACROCYCLIC COMPOUND; ORGANOTIN COMPOUND; THIOCARBAMIC ACID DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; HYDROPHOBICITY; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; THERMOGRAVIMETRY; X RAY CRYSTALLOGRAPHY;

AMINO ACIDS; ANIONS; CATIONS; CRYSTALLOGRAPHY, X-RAY; HYDROPHOBICITY; LIGANDS; MACROCYCLIC COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; ORGANOTIN COMPOUNDS; SPECTROPHOTOMETRY, INFRARED; THERMOGRAVIMETRY; THIOCARBAMATES;

EID: 56649085038     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic8007987     Document Type: Article

References (156)

1. For recent reviews, see: (a) Rao, C. N. R.; Natarajan, S.; Vaidhyanathan, R. Angew. Chem. Int. Ed. 2004, 43, 1466-1496.
2. (b) Würthner, F.; You, C.-C.; Saha-Möller, C. R. Chem. Soc. Rev. 2004, 33, 133-146.
3. (c) Hosseini, M. W. Acc. Chem. Res. 2005, 38, 313-323.
4. (d) Rowsell, J. L. C.; Yaghi, O. M. Angew. Chem., Int. Ed. 2005, 44, 4670-4679.
5. (e) Nitscnke, J. R. Acc. Chem. Res. 2007, 40, 103-112.
6. (f) Pitt, M. A.; Johnson, D. W. Chem. Soc. Rev. 2007, 36, 1441-1453.
7. (g) Thomas, J. A. Chem. Soc. Rev. 2007, 36, 856-868.
8. For representative examples, see: (a) Serpaggi, F.; Ferey, G. Inorg. Chem. 1999, 38, 4741-4744.
9. (b) Evans, O. R.; Xiong, R.-G.; Wang, Z.; Wong, G. K.; Lin, W. Angew. Chem., Int. Ed. 1999, 38, 536-538.
10. (c) Zheng, L.-M.; Wang, X.; Jacobson, A. J. J. Solid State Chem. 2000, 152, 174-182.
11. (d) Dong, Y.-B.; Smith, M. D.; zur Loye, H.-C. Angew. Chem., Int. Ed. 2000, 39, 4271-4273.
12. (e) Su, C.-Y.; Yang, X.-P.; Kang, B.-S.; Mak, T. C. W. Angew. Chem., Int. Ed. 2001, 40, 1725-1728.
13. (f) Barnett, S. A.; Blake, A. J.; Champness, N. R.; Wilson, C. Chem. Commun. 2002, 1640-1641.
14. (g) Halper, S. R.; Cohen, S. M. Angew. Chem., Int. Ed. 2004, 43, 2385-2388.
15. (j) Aakeröy, C. B.; Desper, J.; Levin, B.; Valdes-Martinez, J. Inorg. Chim Acta 2006, 359, 1255-1262.
16. (h) Salazar-Mendoza, D.; Bandron, S. A.; Hosseini, M. W. Chem. Commun. 2007, 2252-2254.
17. (i) Woodward, F. M.; Gibson, P. J.; Jameson, G. B.; Laudee, C. P.; Turnbull, M. M.; Willett, R. D. Inorg. Chem. 2007, 46, 4256-4266.
18. For reports on organotin derivatives of amino acids, see: (a) Pellerito, L.; Nagy, L. Coord. Chem. Rev. 2002, 224, 111-150.
19. (b) Ronconi, L.; Marzano, C.; Russo, U.; Sitran, S.; Graziani, R.; Fregona, D. J. Inorg. Biochem. 2002, 91, 413-420.
20. (c) Nath, M.; Pokharia, S.; Eng, G.; Song, X.; Kumar, A. J. Organomet. Chem. 2003, 669, 109-123.
21. For reviews, see: (a) Tiekink, E. R. T. CrystEngComm 2003, 5, 101-113.
22. (b) Cookson, J.; Beer, P. D. Dalton Trans. 2007, 1459-1472.
23. (c) Tiekink, E. R. T. Appl. Organomet. Chem. 2008, 22, 533-550.
24. For macrocyclic diorganotin bis-difhiocarbamates, see: (a) Jung, O.-S.; Sohn, Y. S.; Ibers, J. A. Inorg. Chem. 1986, 25, 2273-2275.
25. (b) Lee, W. H.; Jung, O.-S.; Sohn, Y. S. Bull. Korean Chem. Soc. 1986, 7, 421-425.
26. (c) Reyes-Martínez, R.; Mejia-Huicochea, R.; Guerrero-Alvarez, A. A.; Höpfl, H.; Tlahuext, H. Arkivoc 2008, V, 19-30.
27. (a) Lai, S. W.; Drew, M. G. B.; Beer, P. D. J. Organomet. Chem. 2001, 637-639, 89-93.
28. (b) Uppadine, L. H.; Weeks, J. M.; Beer, P. D. J. Chem. Soc., Dalton Trans. 2001, 3367-3372.
29. (c) Beer, P. D.; Berry, N.; Drew, M. G. B.; Fox, O. D.; Padilla-Tosta, M. E.; Patell, S. Chem. Commun. 2001, 199-200.
30. (d) Unoura, K.; Abiko, Y.; Yamazaki, A.; Kato, Y.; Coomber, C.; Fallon, G. D.; Nakahara, K.; Bond, A. M. Inorg. Chim. Acta 2002, 333, 41-50.
31. (e) Pratt, M. D.; Beer, P. D. Tetrahedron 2004, 60, 11227-11238.
32. (f) Wong, W. W. H.; Phipps, D. E.; Beer, P. D. Polyhedron 2004, 23, 2821-2829.
33. (g) Wong, W. W. H.; Curiel, D.; Cowley, A. R.; Beer, P. D. Dalton Trans. 2005, 359-364.
34. (a) Fox, O. D.; Drew, M. G. B.; Beer, P. D. Angew. Chem., Int. Ed. 2000, 39, 136-140.
35. (b) Fox, O. D.; Drew, M. G. B.; Wilkinson, E. J. S.; Beer, P. D. Chem. Commun. 2000, 391-392.
36. (c) Beer, P. D.; Cheetham, A. G.; Drew, M. G. B.; Fox, O. D.; Hayes, E. J.; Rolls, T. D. Dalton Trans. 2003, 603-611.
37. (d) Beer, P. D.; Berry, N. G.; Cowley, A. R.; Hayes, E. J.; Oates, E. C.; Wong, W. W. H. Chem. Commun. 2003, 2408-2409.
38. (e) Webber, P. R. A.; Drew, M. G. B.; Hibbert, R.; Beer, P. D. Dalton Trans. 2004, 1127-1135.
39. (a) Padilla-Tosta, M. E.; Fox, O. D.; Drew, M. G. B.; Beer, P. D. Angew. Chem., Int. Ed. 2001, 40, 4235-4239.
40. (b) Wong, W. W. H.; Cookson, J.; Evans, E. A. L.; McInnes, E. J. L.; Wolowska, J.; Maher, J. P.; Bishop, P.; Beer, P. D. Chem. Commun. 2005, 2214-2216.
41. (a) Yu, S.-Y.; Zhang, Z.-X.; Cheng, E. C.-C.; Li, Y.-Z.; Yam, V. W.-W.; Huang, H.-P.; Zhang, R. J. Am. Chem. Soc. 2005, 127, 17994-17995.
42. (b) Zhao, Y.; Pérez-Segarra, W.; Shi, Q.; Wei, A. J. Am. Chem. Soc. 2005, 127, 7328-7329.
43. (c) Konarev, D. V.; Kovalevsky, A. Y.; Khasanov, S. S.; Saito, G.; Lopatin, D. V.; Umrikhin, A. V.; Otsuka, A.; Lyubovskaya, R. N. Eur. J. Inorg. Chem. 2006, 1881-1895.
44. (d) Vickers, M. S.; Cookson, J.; Beer, P. D.; Bishop, P. T.; Thiebaut, B. J. Mater. Chem. 2006, 16, 209-215.
45. (a) Castillo, M.; Criado, J. J.; Macias, B.; Vaquera, M. V. Inorg. Chim. Acta 1986, 124, 127-132.
46. (b) Criado, J. J.; Carrasco, A.; Macias, B.; Salas, J. M.; Medarde, M.; Castillo, M. Inorg. Chim. Acta 1989, 160, 37-42.
47. (c) Criado, J. J.; Fernandez, I.; Macias, B.; Salas, J. M.; Nedarde, M. Inorg. Chim. Acta 1990, 174, 67-75.
48. (d) Macias, B.; Criado, J. J.; Vaquera, M. V.; Villa, M. V.; Castillo, M. J. Inorg. Biochem. 1991, 42, 17-24.
49. (e) Criado, J. J.; Lopez-Arias, J. A.; Macias, B.; Fernandez-Lago, L. R.; Salas, J. M. Inorg. Chim. Acta 1992, 193, 229-235.
50. (f) Macias, B.; Criado, J. J.; Villa, M. V.; Iglesias, M. R.; Castillo, M. Polyhedron 1993, 12, 501-505.
51. (g) Macias, B.; Criado, J. J.; Villa, M. V.; Rodriguez, L. J.; Castillo, M. Polyhedron 1993, 12, 2791-2799.
52. (h) Macias, B.; Villa, M. V.; Martin-Simon, M. Trans. Met. Chem. 1999, 24, 533-536.
53. (i) Macias, B.; Villa, M. V.; Chicote, E.; Martin-Velasco, S.; Castineiras, A.; Borras, J. Polyhedron 2002, 21, 1899-1904.
54. (a) Cao, R.; Travieso, N.; Fragoso, A.; Villalonga, R.; Diaz, A.; Martinez, M. E.; Alpizar, J.; West, D. X. J. Inorg. Biochem. 1997, 66, 213-217.
55. (b) Fujii, S.; Yoshimura, T. Coord. Chem. Rev. 2000, 198, 89-99.
56. (c) El-Said, A. I.; Zidan, A. S. A.; El-Meligy, M. S.; Aly, A. A. M.; Mohammed, O. F. Trans. Metal Chem. 2001, 26, 13-19.
57. (d) Baird, I. R.; Cameron, B. R.; Skerlj, R. T. Inorg. Chim. Acta 2003, 353, 107-118.
58. (a) Sedaghat, T.; Goodarzi, K. Main Group Chem. 2005, 4, 121-126.
59. (b) Sedaghat, T.; Goodarzi, K. Phosphorus, Sulfur Silicon 2007, 182, 2227-2233.
60. For reviews on macrocyclic and supramolecular assemblies based on organometallic species of main group elements, see: (a) Uhl, W. Chem. Soc. Rev. 2000, 29, 259-265.
61. (b) Haiduc, I.; Edelmann, F. T. Supramolecular Organometallic Chemistry; Wiley-VCH: New York, 2000.
62. (c) Chandrasekhar, V.; Nagendran, S.; Baskar, V. Coord. Chem. Rev. 2002, 235, 1-52.
63. (d) Höpfl, H. Structure and Bonding; Roesky, H. W., Atwood, A., Eds.; Springer Verlag: Berlin, 2002; Vol. 103, pp 1-56.
64. (e) Chandrasekhar, V.; Gopal, K.; Thilagar, P. Acc. Chem. Res. 2007, 40, 420-434.
65. (f) Höpfl, H. In Tin Chemistry: Fundamentals, Frontiers and Applications; Davies, A. G., Gielen, M., Panell, K. H., Tiekink, E. R. T., Eds.; Wiley-VCH: New York, 2008.
66. (a) Linton, B.; Hamilton, A. D. Chem. Rev. 1997, 97, 1669-1680.
67. (b) Schmidtchen, F. D.; Berger, M. Chem. Rev. 1997, 97, 1609-1646.
68. (c) Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 41, 486-516.
69. (d) Suksai, C.; Tuntulani, T. Chem. Soc. Rev. 2003, 32, 192-202.
70. (e) Vilar, R. Angew. Chem., Int Ed. 2003, 42, 1460-1477.
71. (f) Beer, P. D.; Hayes, E. J. In Encyclopedia of Supramolecular Chemistry; Atwood, J. L., Steed, J. W., Eds.; Marcel Dekker, Inc.: New York, 2004; Vol. 2, pp 1006-1013.
72. (g) Darbost, U.; Sénèque, O.; Li, Y.; Bertho, G.; Marrot, J.; Rager, M.-N.; Reinaud, O.; Jabin, I. Chem. - Eur. J. 2007, 13, 2078-2088.
73. For representative examples of ion-pair recognition, see: (a) Piotrowski, H.; Hilt, G.; Schulz, A.; Mayer, P.; Polborn, K.; Severin, K. Chem. - Eur. J. 2001, 7, 3196-3208.
74. (b) Lehaire, M. L.; Scopelliti, R.; Piotrowski, H.; Severin, K. Angew. Chem., Int. Ed. Engl. 2002, 41, 1419-1422.
75. (c) Atwood, J. L.; Szumna, A. Chem. Commun. 2003, 940-941.
76. (d) Smith, B. D.; Mahoney, J. M. In Encyclopedia of Supramolecular Chemistry; Atwood, J. L., Steed, J. W., Eds.; Marcel Dekker, Inc.: New York, 2004; Vol. 2, pp 1291-1294.
77. (e) Custelcean, R.; Delmau, L. H.; Moyer, B. A.; Sessler, J. L.; Cho, W.-S.; Gross, D.; Bates, G. W.; Brooks, S. J.; Light, M. E.; Gale, P. A. Angew. Chem., Int. Ed. 2005, 44, 2537-2542.
78. (a) Newcomb, M.; Madonik, A. M.; Blanda, M. T.; Judice, J. K. Organometallics 1987, 6, 145-150.
79. (b) Jurkschat, K.; Uhlig, W.; Mügge, C.; Tzschach, A. Z. Anorg. Allg. Chem. 1988, 556, 161-169.
80. (c) Altmann, R.; Gausset, O.; Horn, D.; Jurkschat, K.; Schürmann, M. Organometallics 2000, 19, 430-443.
81. (a) Newcomb, M.; Horner, J. H.; Blanda, M. T. J. Am. Chem. Soc. 1987, 109, 7878-7879.
82. (b) Horner, J. H.; Squattrito, P. J.; McGuire, N.; Riebenspies, J. P.; Newcomb, M. Organometallics 1991, 10, 1741-1750.
83. Blanda, M. T.; Herren, M. A. Chem. Comm. 2000, 343-344.
84. (a) Zobel, B.; Duthie, A.; Dakternieks, D. E.; Tiekink, E. R. T. Organometallics 2001, 20, 3347-3350.
85. (b) Dakternieks, D. E.; Jurkschat, K.; Zhu, H.; Tiekink, E. R. T. Organometallics 1995, 14, 2512-2521.
86. Xie, Y.; Morimoto, T.; Furuta, H. Angew. Chem., Int. Ed. 2006, 45, 6907-6910.
87. Reeske, G.; Bradtmöller, G.; Schürmann, M.; Jurkschat, K. Chem. - Eur. J. 2007, 13, 10239-10245.
88. For reviews, see: (a) Tiekink, E. R. T. Appl. Organomet. Chem. 1991, 5, 1-23.
89. (b) Tiekink, E. R. T. Main Group Met. Chem. 1992, 15, 161-186.
90. (a) Lockhart, T. P. Organometallics 1988, 7, 1438-1443.
91. (b) Meunier-Piret, J.; Boualam, M.; Willem, R.; Gielen, M. Main Group Met. Chem. 1993, 16, 329-334.
92. (c) Baul, T. S. B.; Tiekink, E. R. T. Z. Kristallogr. 1998, 213, 62-68.
93. (d) Pettinari, C.; Marchetti, F.; Pettinari, R.; Martini, D.; Drozdov, A.; Troyanov, S. J. Chem. Soc., Dalton Trans. 2001, 1790-1797.
94. (e) Beltran, H. I.; Zamudio-Rivera, L. S.; Mancilla, T.; Santillan, R.; Farfan, N. Chem. - Eur. J. 2003, 9, 2291-2306.
95. (f) Ma, C.; Jiang, Q.; Zhang, R. J. Organomet. Chem. 2003, 678, 148-155.
96. (g) Ma, C.; Han, Y.; Zhang, R.; Wang, D. Dalton Trans. 2004, 1832-1840.
97. (h) Ma, C.; Jiang, Q.; Zhang, R. Can. J. Chem. 2004, 82, 608-615.
98. (i) Prabusankar, G.; Murugavel, R. Organometallics 2004, 23, 5644-5647.
99. (j) Baul, T. S. B.; Singh, K. S.; Lyčka, A.; Holčapek, M.; Linden, A. J. Organomet. Chem. 2005, 690, 1581-1587.
100. (k) Baul, T. S. B.; Masharing, C.; Willem, R.; Biesemans, M.; Holčapek, M.; Jirásko, R.; Linden, A. J. Organomet. Chem. 2005, 690, 3080-3094.
101. (l) Baul, T. S. B.; Singh, K. S.; Holčapek, M.; Jirásko, R.; Rivarola, E.; Linden, A. J. Organomet. Chem. 2005, 690, 4232-4242.
102. (m) Ma, C.; Li, J.; Zhang, R.; Wang, D. Inorg. Chim. Acta 2005, 358, 4575-4580.
103. (n) Bowen, R. J.; Caddy, J.; Fernandes, M. A.; Layh, M.; Mamo, M. A.; Meijboom, R. J. Organomet. Chem. 2006, 691, 717-725.
104. (o) Ma, C.; Zhang, Q.; Zhang, R.; Wang, Chem. - Eur. J. 2006, 12, 420-428.
105. (p) Chandrasekhar, V.; Thirumoorthi, R. Organometallics 2007, 26, 5415-5422.
106. (q) Yin, H. D.; Li, F. H.; Wang, C. H. Inorg. Chim. Acta 2007, 360, 2797-2808.
107. (a) Garcia-Zarracino, R.; Ramos-Quiñones, J.; Höpfl, H. Inorg. Chem. 2003, 42, 3835-3845.
108. (b) Garcia-Zarracino, R.; Höpfl, H. Angew. Chem., Int. Ed. 2004, 43, 1507-1511.
109. (c) Zamudio-Rivera, L. S.; George-Tellez, R.; Lopez-Mendoza, G.; Morales-Pacheco, A.; Flores, E.; Höpfl, H.; Barba, V.; Fernandez, F. J.; Cabirol, N.; Beltran, H. I. Inorg. Chem. 2005, 44, 5370-5378.
110. (d) Garcia-Zarracino, R.; Höpfl, H. J. Am. Chem. Soc. 2005, 127, 3120-3130.
111. (e) Hernandez-Ahuactzi, I. F.; Cruz-Huerta, J.; Barba, V.; Höpfl, H.; Zamudio-Rivera, L. S.; Beltran, H. I. Eur. J. Inorg. Chem. 2008, 1200-1204.
112. Escalante, J.; Carrillo-Morales, M.; Linzaga, I. Molecules 2008, 13, 340-347.
113. (a) SMART: Bruker Molecular Analysis Research Tool, versions 5.057, 5.618; Bruker Analytical X-ray Systems: Madison, WI, 1997, 2000.
114. (b) SAINT + NT, versions 6.01, 6.04; Bruker Analytical X-ray Systems: Madison, WI, 1999, 2001.
115. (c) Sheldrick, G. M. SHELX86, Program for Crystal Structure Solution; University of Göttingen: Göttingen, Germany, 1986.
116. (d) SHELXTL-NT, versions 5.10, 6.10; Bruker Analytical X-ray Systems: Madison, WI, 1999, 2000.
117. Mercury, new software for searching the Cambridge Structural Database and visualizing crystal structures, version 1.4.1: Bruno, I. J.; Cole, J. C.; Edgington, P. R.; Kessler, M.; Macrae, C. F.; McCabe, P.; Pearson, J.; Taylor, R. Acta Crystallogr. 2002, 58, 389-397.
118. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. J.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S.; Windus, T. L.; Dupuis, M.; Montgomery, J. A. J. Comput.Chem. 1993, 14, 1347-1363.
119. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B: Condens. Matter Mater. Phys. 1988, 37, 785-789.
120. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
121. Cundari, T. R.; Stevens, W. J. J. Chem. Phys. 1993, 98, 5555-5565.
122. Stevens, W. J.; Basch, H.; Krauss, M. J. Chem. Phys. 1984, 81, 6026-6033.
123. Stevens, W. J.; Basch, H.; Krauss, M.; Jasien, P. Can. J. Chem. 1992, 70, 612-630.
124. Chemcraft v1.5. http://www.chemcraftprog.com (accessed Sep. 2008).
125. Heard, P. J. Main Group Dithiocarbamate Complexes. In Progress in Inorganic Chemistry; John Wiley & Sons: New Jersey, 2005; Vol. 53, pp 1-70.
126. Deacon, G. B.; Phillips, R. J. Coord. Chem. Rev. 1980, 33, 227-250.
127. (a) Durgaprasad, G.; Sathyanarayana, D. N.; Patel, C. C. Can. J. Chem. 1969, 47, 631-635.
128. (b) Brown, D. A.; Glass, W. K.; Burke, M. A. Spectrochim. Acta 1976, 32A, 137-143.
129. (c) Kellner, R.; Nikolov, G. S.; Trendafilova, N. Inorg. Chim. Acta 1984, 84, 233-239.
130. (d) Chandra, S.; Magee, R. J.; James, B. D. Main Group Met. Chem. 1988, 11, 57-65.
131. van Gaal, H. L. M.; Diesveld, J. W.; Pijpers, F. W.; van der Linden, J. G. M. Inorg. Chem. 1979, 18, 3251-3260.
132. (a) Wengrovius, J. H.; Garbauskas, M. F. Organometallics 1992, 11, 1334-1342.
133. (b) Beckmann, J.; Jurkschat, K.; Schollmeyer, D.; Schürmann, M. J. Organomet. Chem. 1997, 543, 229-232.
134. (c) Mehring, M.; Schürmann, M.; Paulus, I.; Horn, D.; Jurkschat, K.; Orita, A.; Otera, J.; Dakternieks, D.; Duthie, A. J. Organomet. Chem. 1999, 574, 176-192.
135. (d) Beckmann, J.; Jurkschat, K. Coord. Chem. Rev. 2001, 215, 267-300.
136. (a) Smith, P. J.; Tupciauskas, A. P. Ann. Rep. NMR Spectrosc. 1978, 8, 291-370.
137. (b) Wrackmeyer, B. Ann. Rep. NMR Spectrosc. 1985, 16, 73-186.
138. García-Zarracino, R.; Ramos-Quiñones, J.; Höpfl, H. J. Organomet. Chem. 2002, 664, 188-200.
139. (a) DeVries, J. L. K. F.; Herber, R. H. Inorg. Chem. 1972, 11, 2458-2464.
140. (b) Tse, J. S.; Sham, T. K.; Bancroft, G. M. Can. J. Chem. 1979, 57, 2223-2229.
141. Lockhart, T. P.; Manders, W. F. Inorg. Chem. 1986, 25, 892-895.
142. (a) Dakternieks, D.; Zhu, H.; Masi, D.; Mealli, C. Inorg. Chem. 1992, 31, 3601-3606.
143. (b) Hook, J. M.; Linahan, B. M.; Taylor, R. L.; Tiekink, E. R. T.; van Gorkom, L.; Webster, L. K. Main Group Met. Chem. 1994, 17, 293-311.
144. (a) Kimura, T.; Yasuoka, N.; Kasai, N.; Kakudo, M. Bull. Chem. Soc. Jpn. 1972, 45, 1649-1954.
145. (b) Lockhart, T. P.; Manders, W. F.; Schlemper, E. O. J. Am. Chem. Soc. 1985, 107, 7451-7453.
146. (c) Holt, E. M.; Nasser, F. A. K.; Wilson, A.; Zuckerman, J. J. Organometallics 1985, 4, 2073-2080.
147. (d) Lokaj, J.; Kellö, E.; Kettmann, V.; Vrabel, V.; Rattay, V. Collect. Czech. Chem. Commun. 1986, 51, 2521-2527.
148. (e) Seth, N.; Gupta, V. D.; Nöth, H.; Thomann, M. Chem. Ber. 1992, 125, 1523-1528.
149. (f) Sharma, J.; Singh, Y.; Bohra, R.; Rai, A. K. Polyhedron 1996, 15, 1097-1102.
150. (g) Menezes, D. C.; de Lima, G. M.; Porto, A. O.; Donnici, C. L.; Ardisson, J. D.; Doriguetto, A. C.; Ellena, J. Polyhedron 2004, 23, 2103-2109.
151. (a) Wheeler, K. A.; Harrington, B.; Zapp, M.; Casey, E. CrystEngComm 2003, 5, 337-342.
152. (b) Allen, F. H.; Bird, C. M.; Rowland, R. S.; Raithby, P. R. Acta Crystallogr., Sect. B 1997, 53, 680-695.
153. For a review, see: (a) Hosseini, M. W. Acc. Chem. Res. 2005, 38, 313-323.
154. UV-vis spectra for the unsubstituted dithiocarbamate anion and the N,N′-dimethyl dithiocarbamate anion were calculated by the time-dependent density functional theory method (TDDFT) as implemented in the Spartan 2006 software. The B3-LYP/6-31+G** approximation was employed to optimize the geometries. These calculations predicted two forbidden n → π* transitions and at lower energy two π → π* transitions polarized along different axes in the x-y plane. See also: (a) Rang, K.; Sandstrom, J. J. Chem. Soc., Perkin Trans. 2 2001, 827-832.
155. (b) Fabian, J. Theor. Chem. Acc. 2001, 106, 199-217.
156. - initiates decomposition of the macrocyles found in compounds 6 and 7.