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Volumn 23, Issue 9, 2004, Pages 2137-2145

Neutral square-planar olefin/alkyl platinum(ii) complexes containing a N,N′-imino-amide ligand. Experimental and theoretical evidence of relevant π-back-donation in the platinum-olefin bond

Author keywords

[No Author keywords available]

Indexed keywords

CORRELATION METHODS; ISOMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PARAMETER ESTIMATION; PROBABILITY DENSITY FUNCTION; PROTONS; SOLUTIONS; SYNTHESIS (CHEMICAL); THERMAL EFFECTS; X RAY DIFFRACTION;

EID: 2442532947     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om049968k     Document Type: Article
Times cited : (31)

References (58)
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    • note
    • "M" and "0" indicate groups that stay in cis positions with respect to methyl and olefin groups, respectively, "u" and "d" discriminate the up and down isopropyl orientations with respect to the olefin R group. Finally, "b" and "f" stand for backward and forward with respect to the plane containing the two phenyl groups (assumed to be coplanar).
  • 11
    • 2442581662 scopus 로고    scopus 로고
    • note
    • 8 on the ligand arm trans to the olefin was possible by observation of either a weak NOE between the olefin R group and "Md" resonances or a weak NOE between CH(Ou) and CH(Mu) or CH(Od) and CH(Md), respectively.
  • 14
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    • Pergamon Press: New York
    • For relevant studies on platinum (II) complexes, see: (a) Hartley, F. R. In Comprehensive Organometallic Chemistry; Pergamon Press: New York, 1982; Vol. 6, p 471. (b) Jesse, A. C.; Stufkens, D. J.; Vrieze, K. Inorg. Chim. Acta 1979, 32, 87-91. (c) Meester, M. A. M.; Stufkens, D. J.; Vrieze, K. Inorg. Chim. Acta 1977, 21, 251-258. (d) Cooper, D. J.; Powell, J. Inorg. Chem. 1978, 15, 1959-1968. (e) Nyburg, S. C.; Simpson, K.; Wong-Ng, W. J. Chem. Soc., Dalton Trans. 1978, 1865-1870. (f) Meester, M. A. M.; van Dam, H.; Stufkens, D. J.; Oskam, A. Inorg. Chim. Acta 1976, 20, 155-160. (g) Chisholm, M. H.; Clark, H. C.; Manzer, L. E.; Stothers, J. B.; Ward, J. E. H. J. Am. Chem. Soc. 1975, 97, 721-727. (h) Olah, G. A.; Mo, Y. K. J. Am. Chem. Soc. 1972, 94, 9244-9246. (i) Chisholm, M. H.; Clark, H. C.; Manzer, L. E.; Stothers, J. B. J. Chem. Soc. 1972, 94, 5087-5089.
    • (1982) Comprehensive Organometallic Chemistry , vol.6 , pp. 471
    • Hartley, F.R.1
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    • For relevant studies on platinum (II) complexes, see: (a) Hartley, F. R. In Comprehensive Organometallic Chemistry; Pergamon Press: New York, 1982; Vol. 6, p 471. (b) Jesse, A. C.; Stufkens, D. J.; Vrieze, K. Inorg. Chim. Acta 1979, 32, 87-91. (c) Meester, M. A. M.; Stufkens, D. J.; Vrieze, K. Inorg. Chim. Acta 1977, 21, 251-258. (d) Cooper, D. J.; Powell, J. Inorg. Chem. 1978, 15, 1959-1968. (e) Nyburg, S. C.; Simpson, K.; Wong-Ng, W. J. Chem. Soc., Dalton Trans. 1978, 1865-1870. (f) Meester, M. A. M.; van Dam, H.; Stufkens, D. J.; Oskam, A. Inorg. Chim. Acta 1976, 20, 155-160. (g) Chisholm, M. H.; Clark, H. C.; Manzer, L. E.; Stothers, J. B.; Ward, J. E. H. J. Am. Chem. Soc. 1975, 97, 721-727. (h) Olah, G. A.; Mo, Y. K. J. Am. Chem. Soc. 1972, 94, 9244-9246. (i) Chisholm, M. H.; Clark, H. C.; Manzer, L. E.; Stothers, J. B. J. Chem. Soc. 1972, 94, 5087-5089.
    • (1979) Inorg. Chim. Acta , vol.32 , pp. 87-91
    • Jesse, A.C.1    Stufkens, D.J.2    Vrieze, K.3
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    • For relevant studies on platinum (II) complexes, see: (a) Hartley, F. R. In Comprehensive Organometallic Chemistry; Pergamon Press: New York, 1982; Vol. 6, p 471. (b) Jesse, A. C.; Stufkens, D. J.; Vrieze, K. Inorg. Chim. Acta 1979, 32, 87-91. (c) Meester, M. A. M.; Stufkens, D. J.; Vrieze, K. Inorg. Chim. Acta 1977, 21, 251-258. (d) Cooper, D. J.; Powell, J. Inorg. Chem. 1978, 15, 1959-1968. (e) Nyburg, S. C.; Simpson, K.; Wong-Ng, W. J. Chem. Soc., Dalton Trans. 1978, 1865-1870. (f) Meester, M. A. M.; van Dam, H.; Stufkens, D. J.; Oskam, A. Inorg. Chim. Acta 1976, 20, 155-160. (g) Chisholm, M. H.; Clark, H. C.; Manzer, L. E.; Stothers, J. B.; Ward, J. E. H. J. Am. Chem. Soc. 1975, 97, 721-727. (h) Olah, G. A.; Mo, Y. K. J. Am. Chem. Soc. 1972, 94, 9244-9246. (i) Chisholm, M. H.; Clark, H. C.; Manzer, L. E.; Stothers, J. B. J. Chem. Soc. 1972, 94, 5087-5089.
    • (1977) Inorg. Chim. Acta , vol.21 , pp. 251-258
    • Meester, M.A.M.1    Stufkens, D.J.2    Vrieze, K.3
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    • For relevant studies on platinum (II) complexes, see: (a) Hartley, F. R. In Comprehensive Organometallic Chemistry; Pergamon Press: New York, 1982; Vol. 6, p 471. (b) Jesse, A. C.; Stufkens, D. J.; Vrieze, K. Inorg. Chim. Acta 1979, 32, 87-91. (c) Meester, M. A. M.; Stufkens, D. J.; Vrieze, K. Inorg. Chim. Acta 1977, 21, 251-258. (d) Cooper, D. J.; Powell, J. Inorg. Chem. 1978, 15, 1959-1968. (e) Nyburg, S. C.; Simpson, K.; Wong-Ng, W. J. Chem. Soc., Dalton Trans. 1978, 1865-1870. (f) Meester, M. A. M.; van Dam, H.; Stufkens, D. J.; Oskam, A. Inorg. Chim. Acta 1976, 20, 155-160. (g) Chisholm, M. H.; Clark, H. C.; Manzer, L. E.; Stothers, J. B.; Ward, J. E. H. J. Am. Chem. Soc. 1975, 97, 721-727. (h) Olah, G. A.; Mo, Y. K. J. Am. Chem. Soc. 1972, 94, 9244-9246. (i) Chisholm, M. H.; Clark, H. C.; Manzer, L. E.; Stothers, J. B. J. Chem. Soc. 1972, 94, 5087-5089.
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    • Cooper, D.J.1    Powell, J.2
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    • For relevant studies on platinum (II) complexes, see: (a) Hartley, F. R. In Comprehensive Organometallic Chemistry; Pergamon Press: New York, 1982; Vol. 6, p 471. (b) Jesse, A. C.; Stufkens, D. J.; Vrieze, K. Inorg. Chim. Acta 1979, 32, 87-91. (c) Meester, M. A. M.; Stufkens, D. J.; Vrieze, K. Inorg. Chim. Acta 1977, 21, 251-258. (d) Cooper, D. J.; Powell, J. Inorg. Chem. 1978, 15, 1959-1968. (e) Nyburg, S. C.; Simpson, K.; Wong-Ng, W. J. Chem. Soc., Dalton Trans. 1978, 1865-1870. (f) Meester, M. A. M.; van Dam, H.; Stufkens, D. J.; Oskam, A. Inorg. Chim. Acta 1976, 20, 155-160. (g) Chisholm, M. H.; Clark, H. C.; Manzer, L. E.; Stothers, J. B.; Ward, J. E. H. J. Am. Chem. Soc. 1975, 97, 721-727. (h) Olah, G. A.; Mo, Y. K. J. Am. Chem. Soc. 1972, 94, 9244-9246. (i) Chisholm, M. H.; Clark, H. C.; Manzer, L. E.; Stothers, J. B. J. Chem. Soc. 1972, 94, 5087-5089.
    • (1978) J. Chem. Soc., Dalton Trans. , pp. 1865-1870
    • Nyburg, S.C.1    Simpson, K.2    Wong-Ng, W.3
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    • 0011585692 scopus 로고
    • For relevant studies on platinum (II) complexes, see: (a) Hartley, F. R. In Comprehensive Organometallic Chemistry; Pergamon Press: New York, 1982; Vol. 6, p 471. (b) Jesse, A. C.; Stufkens, D. J.; Vrieze, K. Inorg. Chim. Acta 1979, 32, 87-91. (c) Meester, M. A. M.; Stufkens, D. J.; Vrieze, K. Inorg. Chim. Acta 1977, 21, 251-258. (d) Cooper, D. J.; Powell, J. Inorg. Chem. 1978, 15, 1959-1968. (e) Nyburg, S. C.; Simpson, K.; Wong-Ng, W. J. Chem. Soc., Dalton Trans. 1978, 1865-1870. (f) Meester, M. A. M.; van Dam, H.; Stufkens, D. J.; Oskam, A. Inorg. Chim. Acta 1976, 20, 155-160. (g) Chisholm, M. H.; Clark, H. C.; Manzer, L. E.; Stothers, J. B.; Ward, J. E. H. J. Am. Chem. Soc. 1975, 97, 721-727. (h) Olah, G. A.; Mo, Y. K. J. Am. Chem. Soc. 1972, 94, 9244-9246. (i) Chisholm, M. H.; Clark, H. C.; Manzer, L. E.; Stothers, J. B. J. Chem. Soc. 1972, 94, 5087-5089.
    • (1976) Inorg. Chim. Acta , vol.20 , pp. 155-160
    • Meester, M.A.M.1    Van Dam, H.2    Stufkens, D.J.3    Oskam, A.4
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    • 0040806602 scopus 로고
    • For relevant studies on platinum (II) complexes, see: (a) Hartley, F. R. In Comprehensive Organometallic Chemistry; Pergamon Press: New York, 1982; Vol. 6, p 471. (b) Jesse, A. C.; Stufkens, D. J.; Vrieze, K. Inorg. Chim. Acta 1979, 32, 87-91. (c) Meester, M. A. M.; Stufkens, D. J.; Vrieze, K. Inorg. Chim. Acta 1977, 21, 251-258. (d) Cooper, D. J.; Powell, J. Inorg. Chem. 1978, 15, 1959-1968. (e) Nyburg, S. C.; Simpson, K.; Wong-Ng, W. J. Chem. Soc., Dalton Trans. 1978, 1865-1870. (f) Meester, M. A. M.; van Dam, H.; Stufkens, D. J.; Oskam, A. Inorg. Chim. Acta 1976, 20, 155-160. (g) Chisholm, M. H.; Clark, H. C.; Manzer, L. E.; Stothers, J. B.; Ward, J. E. H. J. Am. Chem. Soc. 1975, 97, 721-727. (h) Olah, G. A.; Mo, Y. K. J. Am. Chem. Soc. 1972, 94, 9244-9246. (i) Chisholm, M. H.; Clark, H. C.; Manzer, L. E.; Stothers, J. B. J. Chem. Soc. 1972, 94, 5087-5089.
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    • Chisholm, M.H.1    Clark, H.C.2    Manzer, L.E.3    Stothers, J.B.4    Ward, J.E.H.5
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    • For relevant studies on platinum (II) complexes, see: (a) Hartley, F. R. In Comprehensive Organometallic Chemistry; Pergamon Press: New York, 1982; Vol. 6, p 471. (b) Jesse, A. C.; Stufkens, D. J.; Vrieze, K. Inorg. Chim. Acta 1979, 32, 87-91. (c) Meester, M. A. M.; Stufkens, D. J.; Vrieze, K. Inorg. Chim. Acta 1977, 21, 251-258. (d) Cooper, D. J.; Powell, J. Inorg. Chem. 1978, 15, 1959-1968. (e) Nyburg, S. C.; Simpson, K.; Wong-Ng, W. J. Chem. Soc., Dalton Trans. 1978, 1865-1870. (f) Meester, M. A. M.; van Dam, H.; Stufkens, D. J.; Oskam, A. Inorg. Chim. Acta 1976, 20, 155-160. (g) Chisholm, M. H.; Clark, H. C.; Manzer, L. E.; Stothers, J. B.; Ward, J. E. H. J. Am. Chem. Soc. 1975, 97, 721-727. (h) Olah, G. A.; Mo, Y. K. J. Am. Chem. Soc. 1972, 94, 9244-9246. (i) Chisholm, M. H.; Clark, H. C.; Manzer, L. E.; Stothers, J. B. J. Chem. Soc. 1972, 94, 5087-5089.
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    • Olah, G.A.1    Mo, Y.K.2
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    • 0003277420 scopus 로고
    • For relevant studies on platinum (II) complexes, see: (a) Hartley, F. R. In Comprehensive Organometallic Chemistry; Pergamon Press: New York, 1982; Vol. 6, p 471. (b) Jesse, A. C.; Stufkens, D. J.; Vrieze, K. Inorg. Chim. Acta 1979, 32, 87-91. (c) Meester, M. A. M.; Stufkens, D. J.; Vrieze, K. Inorg. Chim. Acta 1977, 21, 251-258. (d) Cooper, D. J.; Powell, J. Inorg. Chem. 1978, 15, 1959-1968. (e) Nyburg, S. C.; Simpson, K.; Wong-Ng, W. J. Chem. Soc., Dalton Trans. 1978, 1865-1870. (f) Meester, M. A. M.; van Dam, H.; Stufkens, D. J.; Oskam, A. Inorg. Chim. Acta 1976, 20, 155-160. (g) Chisholm, M. H.; Clark, H. C.; Manzer, L. E.; Stothers, J. B.; Ward, J. E. H. J. Am. Chem. Soc. 1975, 97, 721-727. (h) Olah, G. A.; Mo, Y. K. J. Am. Chem. Soc. 1972, 94, 9244-9246. (i) Chisholm, M. H.; Clark, H. C.; Manzer, L. E.; Stothers, J. B. J. Chem. Soc. 1972, 94, 5087-5089.
    • (1972) J. Chem. Soc. , vol.94 , pp. 5087-5089
    • Chisholm, M.H.1    Clark, H.C.2    Manzer, L.E.3    Stothers, J.B.4
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    • 0037427302 scopus 로고    scopus 로고
    • See also, for example: (a) Foley, S. R.; Stockland, S. A., Jr.; Shen, H.; Jordan, R. F. J. Am. Chem. Soc. 2003, 125, 4350-4361. (b) Nicolaides, A.; Smith, J. M.; Kumar, A.; Barnhart, D. M.; Thatcher Borden, W. Organometallica 1995, 14, 3475-3485. (c) Caruso, F.; Camalli, M.; Pellizer, G.; Asaro. F.; Lenarda, M. Inorg. Chim. Acta 1991, 181, 167-176. (d) Mink, L.; Rettig, M. F.; Wing, R. M. J. Am. Chem. Soc. 1991, 113, 2065-2071. (e) Al-Najjar, I. M.; Amin, H. B. J. Chem. Soc., Dalton Trans. 1990, 429-436.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 4350-4361
    • Foley, S.R.1    Stockland Jr., S.A.2    Shen, H.3    Jordan, R.F.4
  • 26
    • 0000450145 scopus 로고
    • See also, for example: (a) Foley, S. R.; Stockland, S. A., Jr.; Shen, H.; Jordan, R. F. J. Am. Chem. Soc. 2003, 125, 4350-4361. (b) Nicolaides, A.; Smith, J. M.; Kumar, A.; Barnhart, D. M.; Thatcher Borden, W. Organometallica 1995, 14, 3475-3485. (c) Caruso, F.; Camalli, M.; Pellizer, G.; Asaro. F.; Lenarda, M. Inorg. Chim. Acta 1991, 181, 167-176. (d) Mink, L.; Rettig, M. F.; Wing, R. M. J. Am. Chem. Soc. 1991, 113, 2065-2071. (e) Al-Najjar, I. M.; Amin, H. B. J. Chem. Soc., Dalton Trans. 1990, 429-436.
    • (1995) Organometallica , vol.14 , pp. 3475-3485
    • Nicolaides, A.1    Smith, J.M.2    Kumar, A.3    Barnhart, D.M.4    Thatcher Borden, W.5
  • 27
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    • See also, for example: (a) Foley, S. R.; Stockland, S. A., Jr.; Shen, H.; Jordan, R. F. J. Am. Chem. Soc. 2003, 125, 4350-4361. (b) Nicolaides, A.; Smith, J. M.; Kumar, A.; Barnhart, D. M.; Thatcher Borden, W. Organometallica 1995, 14, 3475-3485. (c) Caruso, F.; Camalli, M.; Pellizer, G.; Asaro. F.; Lenarda, M. Inorg. Chim. Acta 1991, 181, 167-176. (d) Mink, L.; Rettig, M. F.; Wing, R. M. J. Am. Chem. Soc. 1991, 113, 2065-2071. (e) Al-Najjar, I. M.; Amin, H. B. J. Chem. Soc., Dalton Trans. 1990, 429-436.
    • (1991) Inorg. Chim. Acta , vol.181 , pp. 167-176
    • Caruso, F.1    Camalli, M.2    Pellizer, G.3    Asaro, F.4    Lenarda, M.5
  • 28
    • 0011370762 scopus 로고
    • See also, for example: (a) Foley, S. R.; Stockland, S. A., Jr.; Shen, H.; Jordan, R. F. J. Am. Chem. Soc. 2003, 125, 4350-4361. (b) Nicolaides, A.; Smith, J. M.; Kumar, A.; Barnhart, D. M.; Thatcher Borden, W. Organometallica 1995, 14, 3475-3485. (c) Caruso, F.; Camalli, M.; Pellizer, G.; Asaro. F.; Lenarda, M. Inorg. Chim. Acta 1991, 181, 167-176. (d) Mink, L.; Rettig, M. F.; Wing, R. M. J. Am. Chem. Soc. 1991, 113, 2065-2071. (e) Al-Najjar, I. M.; Amin, H. B. J. Chem. Soc., Dalton Trans. 1990, 429-436.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 2065-2071
    • Mink, L.1    Rettig, M.F.2    Wing, R.M.3
  • 29
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    • See also, for example: (a) Foley, S. R.; Stockland, S. A., Jr.; Shen, H.; Jordan, R. F. J. Am. Chem. Soc. 2003, 125, 4350-4361. (b) Nicolaides, A.; Smith, J. M.; Kumar, A.; Barnhart, D. M.; Thatcher Borden, W. Organometallica 1995, 14, 3475-3485. (c) Caruso, F.; Camalli, M.; Pellizer, G.; Asaro. F.; Lenarda, M. Inorg. Chim. Acta 1991, 181, 167-176. (d) Mink, L.; Rettig, M. F.; Wing, R. M. J. Am. Chem. Soc. 1991, 113, 2065-2071. (e) Al-Najjar, I. M.; Amin, H. B. J. Chem. Soc., Dalton Trans. 1990, 429-436.
    • (1990) J. Chem. Soc., Dalton Trans. , pp. 429-436
    • Al-Najjar, I.M.1    Amin, H.B.2
  • 30
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    • note
    • The only exception is given by an elusive hydrido complex (entry 7 of Table 3), characterized at 180 K due to its tendency to undergo insertion of ethylene into the Pt - H bond.
  • 39
    • 2442606875 scopus 로고    scopus 로고
    • note
    • 25 complexes, where the importance of the π-back-donation contribution is acknowledged.
  • 49
    • 2442543694 scopus 로고    scopus 로고
    • Vrije Universiteit Amsterdam: Amsterdam, The Netherlands
    • ADF 2002, Users Manual; Vrije Universiteit Amsterdam: Amsterdam, The Netherlands, 2000.
    • (2000) ADF 2002, Users Manual
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