Diorganotin(IV) dithiocarbamate complexes as chromogenic sensors of anion binding

Polyhedron

Volumn 28, Issue 18, 2009, Pages 3953-3966

  Fuentes Martínez, Juan Pablo ^a   Toledo Martínez, Isaim ^a   Román Bravo, Perla ^a   García, Patricia García y ^a   Godoy Alcántar, Carolina ^a   López Cardoso, Marcela ^a   Morales Rojas, Hugo ^a  

^a CENTRO DE INVESTIGACIONES QUÍMICAS   (Mexico)

Author keywords

Anion binding; Dithiocarbamate; Ligand exchange; Organotin complexes

Indexed keywords

CARBOXYLATION; CHLORINE COMPOUNDS; FLUORINE COMPOUNDS; LIGANDS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANOMETALLICS; SOLID SOLUTIONS; SYNTHESIS (CHEMICAL); TITRATION;

ANION-BINDING; COMPLEX 1; DICARBOXYLATES; DITHIOCARBAMATES; FIVE-COORDINATION; GENERAL FORMULAS; LIGAND EXCHANGES; ORGANO-TIN COMPLEXES; ORGANOTIN COMPLEX; ORGANOTINS;

NEGATIVE IONS;

EID: 70449627931     PISSN: 02775387     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.poly.2009.09.010     Document Type: Article

References (137)

1. Schmidtchen F.D., and Berger M. Chem. Rev. 97 (1997) 1609
2. Beer P.D., and Gale P.A. Angew. Chem., Int. Ed. 41 (2001) 486
3. Newcomb M., Madonik A.M., Blanda M.T., and Judice J.K. Organometallics 6 (1987) 145
4. Newcomb M., H Horner J., and Blanda M.T. J. Am. Chem. Soc. 109 (1987) 7878
5. Horner J.H., Squattrito P.J., McGuire N., Riebenspies J.P., and Newcomb M. Organometallics 10 (1991) 1741
6. Blanda M.T., and Herren M.A. Chem. Commun. (2000) 343
7. Boshra R., Sundararaman A., Zakharov L.N., Incarvito C.D., Rheingold A.L., and Jäkle F. Chem. Eur. J. 11 (2005) 2810
8. Jurkschat K., Kuivila H.G., Liu S., and Zubieta J.A. Organometallics 8 (1989) 2755
9. Jurkschat K., Hesselbarth F., Dargatz M., Lehmann J., Kleinpeter E., Tzschach A., and Meunier-Piret J. J. Organomet. Chem. 381 (1990) 259
10. Jurkschat K., Rühlemann A., and Tzschach A. J. Organomet. Chem. 381 (1990) C53
11. Dakternieks D.E., Jurkschat K., Zhu H., and Tiekink E.R.T. Organometallics 14 (1995) 2512
12. Altmann R., Jurkschat K., Schürmann M., Dakternieks D., and Duthie A. Organometallics 17 (1998) 5858
13. Altmann R., Gausset O., Horn D., Jurkschat K., Schürmann M., Fontani M., and Zanello P. Organometallics 17 (2000) 430
14. Schulte M., Schürmann M., and Jurkschat K. Chem. Eur. J. 7 (2001) 347
15. Zobel B., Duthie A., Dakternieks D.E., and Tiekink E.R.T. Organometallics 20 (2001) 3347
16. Chaniotakis N., Jurkschat K., Muller D., Perdikaki K., and Reeske G. Eur. J. Inorg. Chem. (2004) 2283
17. Xie Y., Morimoto T., and Furuta H. Angew. Chem., Int. Ed. 45 (2006) 6907
18. For recent reviews:. In: Davies A.G., Gielen M., Panell K.H., and Tiekink E.R.T. (Eds). Tin Chemistry - Fundamentals, Frontiers, and Applications (2008), Wiley-Chichester 413 (Chapter 4)
19. In: Gielen M., and Tiekink E.R.T. (Eds). Metallotherapeutic Drugs and Metal-based Diagnostic agents. The Use of Metals in Medicine (2005), Wiley-Chichester 421
20. Carboxylates:. Rauf M.K., Saeed M.A., Imtiaz-ud-Din, Bolte M., Badshah A., and Mirza B. J. Organomet. Chem. 693 (2008) 3043
21. De Stefano C., Gianguzza A., Giuffre O., Pettignano A., and Sammartano S. Appl. Organomet. Chem. 22 (2008) 30
22. Khan M.I., Baloch M.K., Ashfaq M., Malik A., and Mehsud S. Main Group Met. Chem. 29 (2006) 343
23. Khan M.I., Baloch M.K., Ashfaq M., and Malik A. Bull. Chem. Soc. Jpn. 79 (2006) 1054
24. Khan M.I., Baloch M.K., and Ashfaq M. Appl. Organomet. Chem. 20 (2006) 463
25. Alvarez-Boo P., Casas J.S., Couce M.D., Farto R., Fernandez-Moreira V., Freijanes E., Sordo J., and Vazquez-Lopez E. J. Organomet. Chem. 691 (2006) 45
26. Zhou Y.Z., Jiang T., Ren S.M., Yu J.S., and Xia Z.C. J. Organomet. Chem. 690 (2005) 2186
27. Szorcsik A., Nagy L., Pellerito L., Yamaguchi T., and Yoshida K. J. Radioanal. Nucl. Chem. 256 (2003) 3
28. Aminoacids:. Khan M.I. Main Group Met. Chem. 29 (2006) 201
29. Nath M., Jairath R., Eng G., Song X.Q., and Kumar A. Spectrochim. Acta Part A - Mol. Biomol. Spectrosc. 62 (2005) 1179
30. Mohamed M.M.A. J. Coord. Chem. 56 (2003) 745
31. Heterocycles:. Tripathi U.N., Ahmad M.S., Venubabu G., and Ramakrishna P. J. Coord. Chem. 60 (2007) 1777
32. Valla V., Bakola-Christianopoulou M., Kojic V., Kojic V., and Bogdanovic G. Synth. React. Inorg. Met.-Org. Nano-Met. Chem. 37 (2007) 41
33. Valla V., Bakola-Christianopoulou M., Akrivos P., Kojic V., and Bogdanovic G. Synth. React. Inorg. Met.-Org. Nano-Met. Chem. 36 (2006) 765
34. Tripathi U.N., Venubabu G., Ahmad M.S., Kolisetty S.S.R., and Srivastava A.K. Appl. Organomet. Chem. 20 (2006) 669
35. Joshi A., Verma S., Gaur R.B., and Sharma R.R. Bioinorg. Chem. Appl. 3 (2005) 201
36. Girasolo M.A., Di Salvo C., Schillaci D., Barone G., Silvestri A., and Ruisi G. J. Organomet. Chem. 690 (2005) 4773
37. Nath M., Jairath R., Eng G., Song X.Q., and Kumar A. J. Organomet. Chem. 690 (2005) 134
38. N, O, or S donor ligands:. Nath M., Song X.Q., Eng G., and Kumar A. Spectrochim. Acta Part A - Mol. Biomol. Spectrosc. 70 (2008) 766
39. Joshi R., Kumar P., Kumar S., and Hashmi A.A. J. Coord. Chem. 61 (2008) 2437
40. Hadjikakou S.K., Ozturka I.I., Xanthopoulou M.N., Zachariadis P.C., Zartilas S., Karkabounas S., and Hadjiliadis N. J. Inorg. Biochem. 102 (2008) 1007
41. Koch B., Baul T.S.B., and Chatterjee A.J. Appl. Tox. 28 (2008) 430
42. Shang X.M., Cui J.R., Wu J.Z., Pombeiro A.J.L., and Li Q.S. J. Inorg. Biochem. 102 (2008) 901
43. Xanthopoulou M.N., Hadjikakou S.K., Hadjiliadis N., Milaeva E.R., Gracheva J.A., Tyurin V.Y., Kourkoumelis N., Christoforidis K.C., Metsios A.K., Karkabounas S., and Charalabopoulos K. Eur. J. Med. Chem. 43 (2008) 327
44. Nath M., Pokharia S., Eng G., Song X.Q., and Kumar A. Eur. J. Med. Chem. 40 (2005) 289
45. Nath M., Pokharia S., Eng G., Song X.Q., and Kumar A. Synth. React. Inorg. Met.-Org. Chem. 34 (2004) 1689
46. Chasapis C.T., Hadjikakou S.K., Garoufis A., Hadjiliadis N., Bakas T., Kubicki M., and Ming Y. Bioinorg. Chem. Appl. 2 (2004) 43
47. Nath M., Pokharia S., Eng G., Song X.Q., Kumar A., Gielen M., Willem R., and Biesemans M. Appl. Organomet. Chem. 18 (2004) 460
48. Singh A.K., and Bhandari S. Main Group Met. Chem. 26 (2003) 155
49. Valla V., and Bakola-Christianopoulou M. Synth. React. Inorg. Met.-Org. Nano-Met. Chem. 37 (2007) 507
50. Szorcsik A., Nagy L., Pellerito L., and Lampeka R.D. J. Radioanal. Nucl. Chem. 257 (2003) 285
51. For organotin dithiocarbamates:. Chandra S., James B.D., Macauley B.J., and Magee R.J. J. Chem. Tech. Biotech. 39 (1987) 65
52. Gogoi P.K., Phukan D.P., and Das D.K. Asian J. Chem. 11 (1999) 1291
53. Menezes D.C., Vieira F.T., de Lima G.M., Wardell J.L., Cortés M.E., Ferreira M.P., Soares M.A., and Vilas Boas A. Appl. Organomet. Chem. 22 (2008) 221
54. Menezes D.C., Vieira F.T., de Lima G.M., Porto A.O., Cortés M.E., Ardisson J.D., and Albrecht-Schmitt T.E. Eur. J. Med. Chem. 40 (2005) 1277
55. Shahzadi S., Ali S., Bhatti M.H., Fettouhi M., and Athar M. J. Organomet. Chem. 691 (2006) 1797
56. Shahzadi S., Ali S., and Fettouhi M. J. Chem. Crystallogr. 38 (2008) 273
57. Chauhan H.P.S., and Shaik N.M. J. Inorg. Biochem. 99 (2005) 538
58. Yin H.-D., and Xue S.C. Appl. Organomet. Chem. 20 (2006) 283
59. Gielen M. Appl. Organomet. Chem. 16 (2002) 481
60. Pellerito L. Coord. Chem. Rev. 224 (2002) 111
61. For recent reviews:. In: Davies A.G., Gielen M., Panell K.H., and Tiekink E.R.T. (Eds). Tin Chemistry - Fundamentals, Frontiers, and Applications (2008), Wiley-Chichester 285 (Chapter 3)
62. Heard P.J. Progress in Inorganic Chemistry vol. 55 (2005), John Wiley and Sons, New Jersey 1
63. D. Coucouvanis, in: Progress in Inorganic Chemistry, vol. 26, 1979, p. 301.
64. Lai S.W., Drew M.G.B., and Beer P.D. J. Organomet. Chem. 637-639 (2001) 89
65. Uppadine L.H., Weeks J.M., and Beer P.D. J. Chem. Soc., Dalton Trans. (2001) 3367
66. Beer P.D., Berry N., Drew M.G.B., Fox O.D., Padilla-Tosta M.E., and Patell S. Chem. Commun. (2001) 199
67. Unoura K., Abiko Y., Yamazaki A., Kato Y., Coomber C., Fallon G.D., Nakahara K., and Bond A.M. Inorg. Chim. Acta 333 (2002) 41
68. Pratt M.D., and Beer P.D. Tetrahedron 60 (2004) 11227
69. Wong W.W.H., Phipps D.E., and Beer P.D. Polyhedron 23 (2004) 2821
70. Wong W.W.H., Curiel D., Cowley A.R., and Beer P.D. Dalton Trans. (2005) 359
71. Fox O.D., Drew M.G.B., and Beer P.D. Angew. Chem., Int. Ed. 39 (2000) 136
72. Fox O.D., Drew M.D.G., Wilkinson E.J.S., and Beer P.D. Chem. Commun. (2000) 391
73. Beer P.D., Cheetham A.G., Drew M.G.B., Fox O.D., Hayes E.J., and Rolls T.D. Dalton Trans. (2003) 603
74. Beer P.D., Berry N.G., Cowley A.R., Hayes E.J., Oates E.C., and Wong W.W.H. Chem. Commun. (2003) 2408
75. Webber P.R.A., Drew M.G.B., Hibbert R., and Beer P.D. Dalton Trans. (2004) 1127
76. Padilla-Tosta M.E., Fox O.D., Drew M.G.B., and Beer P.D. Angew. Chem., Int. Ed. 40 (2001) 4235
77. Wong W.W.H., Cookson J., Evans E.A.L., McInnes E.J.L., Wolowska J., Maher J.P., Bishop P., and Beer P.D. Chem. Commun. (2005) 2214
78. Yu S.-Y., Zhang Z.-X., Cheng E.C.-C., Li Y.-Z., Yam V.W.-W., Huang H.-P., and Zhang R. J. Am. Chem. Soc. 127 (2005) 17994
79. Zhao Y., Pérez-Segarra W., Shi Q., and Wei A. J. Am. Chem. Soc. 127 (2005) 7328
80. Konarev D.V., Kovalevsky A.Y., Khasanov S.S., Saito G., Lopatin D.V., Umrikhin A.V., Otsuka A., and Lyubovskaya R.N. Eur. J. Inorg. Chem. (2006) 1881
81. Vickers M.S., Cookson J., Beer P.D., Bishop P.T., and Thiebaut B. J. Mater. Chem. 16 (2006) 209
82. Cookson J., and Beer P.D. J. Chem. Soc., Dalton Trans (2007) 1459
83. Cookson J., Vickers M.S., Paul R.L., Cowley A.R., and Beer P.D. Inorg. Chim. Acta 361 (2008) 1689
84. Hopfl H. In: Davies A.G., Gielen M., Panell K.H., and Tiekink E.R.H. (Eds). Tin Chemistry - Fundamentals, Frontiers, and Applications (2008), Wiley-Chichester 117
85. Garcia-Zarracino R., Ramos-Quiñones J., and Höpfl H. Inorg. Chem. 42 (2003) 3835
86. Garcia-Zarracino R., and Höpfl H. Angew. Chem., Int. Ed. 43 (2004) 1507
87. Zamudio-Rivera L.S., George-Tellez R., Lopez-Mendoza G., Morales-Pacheco A., Flores E., Höpfl H., Barba V., Fernandez F.J., Cabirol N., and Beltran H.I. Inorg. Chem. 44 (2005) 5370
88. Garcia-Zarracino R., and Höpfl H. J. Am. Chem. Soc. 127 (2005) 3120
89. Hernandez-Ahuactzi I.F., Cruz-Huerta J., Barba V., Höpfl H., Zamudio-Rivera L.S., and Beltran H.I. Eur. J. Inorg. Chem. (2008) 1200
90. Reyes-Martínez R., Mejia-Huicochea R., Guerrero-Alvarez J.A., Höpfl H., and Tlahuext H. Arkivoc V (2008) 19
91. Santacruz-Juarez E., Cruz-Huerta J., Hernández-Ahuactzi I.F., Reyes-Martínez R., Tlahuext H., Morales-Rojas H., and Höpfl H. Inorg. Chem. 47 (2008) 9804
92. Lockhart T.P. Organometallics 7 (1988) 1438
93. Meunier-Piret J., Boualam M., Willem R., and Gielen M. Main Group Met. Chem. 16 (1993) 329
94. Baul T.S.B., and Tiekink E.R.H. Z. Kristallogr. 213 (1998) 62
95. Pettinari C., Marchetti F., Pettinari R., Martini D., Drozdov A., and Troyanov S. J. Chem. Soc., Dalton Trans. (2001) 1790
96. Beltran H.I., Zamudio-Rivera L.S., Mancilla T., Santillan R., and Farfan N. Chem. Eur. J. 9 (2003) 2291
97. Ma C., Jiang Q., and Zhang R.J. Organomet. Chem. 678 (2003) 148
98. Ma C., Han Y., Zhang R., and Wang D. Dalton Trans. (2004) 1832
99. Ma C., Jiang Q., and Zhang R. Can. J. Chem. 82 (2004) 608
100. Prabusankar G., and Murugavel R. Organometallics 23 (2004) 5644
101. Baul T.S.B., Singh K.S., Lycka A., Holcapek M., and Linden A. J. Organomet. Chem. 690 (2005) 1581
102. Baul T.S.B., Masharing C., Willem R., Biesemans M., Holcapek M., Jirasko R., and Linden A. J. Organomet. Chem. 690 (2005) 3080
103. Baul T.S.B., Singh K.S., Holcapek M., Jirasko R., Rivarola E., and Linden A. J. Organomet. Chem. 690 (2005) 4232
104. Ma C., Li J., Zhang R., and Wang D. Inorg. Chim. Acta 358 (2005) 4575
105. Bowen R.J., Caddy J., Fernandes M.A., Layh M., Mamo M.A., and Meijboom R. J. Organomet. Chem. 691 (2006) 717
106. Ma C., Zhang Q., and Zhang R. Chem. Eur. J. 12 (2006) 420
107. Chandrasekhar V., and Thirumoorthi R. Organometallics 26 (2007) 5415
108. Yin H.D., Li F.H., and Wang C.H. Inorg. Chim. Acta 360 (2007) 2797
109. Cruz-Huerta J., Carillo-Morales M., Santacruz-Juárez E., Hernández-Ahuactzi I.F., Escalante-García J., Godoy-Alcantar C., Guerrero-Alvarez J.A., Höpfl H., Morales-Rojas H., and Sánchez M. Inorg. Chem. 47 (2008) 9874
110. Lébl T., Smička A., Brus J., and Bruhn C. Eur. J. Inorg. Chem. (2003) 143
111. Lébl T., Zoufalá P., and Bruhn C. Eur. J. Inorg. Chem. (2005) 2536
112. Löwik D.W.P.M., and Lowe C.R. Eur. J. Org. Chem. (2001) 2825
113. Gleu F., and Schwab R. Angew. Chem. 62 (1950) 320
114. Bruker Analytical X-ray Systems. smart: Bruker Molecular Analysis Research Tool, Versions 5.057 and 5.618, 1997 and 2000.
115. Bruker Analytical X-ray Systems. saint+nt, Versions 6.01 and 6.04, 1999 and 2001.
116. G.M. Sheldrick, shelx86, Program for Crystal Structure Solution; University of Göttingen, Germany, 1986.
117. Bruker Analytical X-ray Systems. shelxtl-nt Versions 5.10 and 6.10, 1999 and 2000.
118. Holt E.M., Nasser F.A.K., Wilson Jr. A., and Zuckerman J.J. Organometallics 4 (1985) 2073
119. Durgaprasad G., Sathyanarayana D.N., and Patel C.C. Can. J. Chem. 47 (1969) 631
120. Brown D.A., Glass W.K., and Burke M.A. Spectrochim. Acta 32A (1976) 137
121. Chandra S., Magee R.J., and James B.D. Main Group Met. Chem. 11 (1988) 57
122. Bonati F., and Ugo R. J. Organomet. Chem. 10 (1967) 257
123. van Gaal H.L.M., Diesveld J.W., Pijpers F.W., and van der Linden J.G.M. Inorg. Chem. 18 (1979) 3251
124. Dakternieks D., Zhu J.H., Masi D., and Mealli C. Inorg. Chem. 31 (1992) 3601
125. Hook J.M., Linahan B.M., Taylor R.L., Tiekink E.R.T., van Gorkom L., and Webster L.K. Main Group Met. Chem. 17 (1994) 293
126. Ali S., Ahmad S.U., Sadiq-ur-Rehman, Shahzadi S., Parvaez M., and Mazhhar M. Appl. Organomet. Chem. 19 (2005) 200
127. Dakternieks D.E., Jurkschat K., Schollmeyer D., and Hong W. J. Organomet. Chem. 492 (1995) 145
128. Tiekink E.R.T. Appl. Organomet. Chem. 22 (2008) 533
129. Jung O.S., Jeong J.H., and Sohn Y.S. Organometallics 10 (1991) 761
130. UV-Vis spectra for the unsubstituted dithiocarbamate anion and N,N′-dimethyl dithiocarbamate anion were calculated by the time dependant density functional theory method (TDDFT) as implemented in the Spartan 2006 software. The B3LYP/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:. Rang K., and Sandstrom J. J. Chem. Soc., Perkin Trans 2 (2001) 827
131. Fabian J. Theor. Chem. Acc. 106 (2001) 199
132. Prasanna de Silva A., Gunaratne H.Q.N., Gunnlaugsson T., Huxley A.J.M., McCoy C.P., Rademacher J.T., and Rice T.E. Chem. Rev. 97 (1997) 1515
133. Martinez-Mañez R., and Sancenon F. Chem. Rev. 103 (2003) 4419
134. Suksai C., and Tuntulani T. Chem. Soc. Rev. 32 (2003) 192
135. Bell T.W., and Hext N.M. Chem. Soc. Rev. 33 (2004) 589
136. Valeur B. Molecular Fluorescence: Principles and Applications (2001), VCH (Chapter 10)
137. Lim M.H., and Lippard S.J. Inorg. Chem. 45 (2006) 8980