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Volumn 12, Issue 21, 1996, Pages 5064-5075

Nucleophilic displacements in mixed self-assembled monolayers

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Indexed keywords


EID: 0000148653     PISSN: 07437463     EISSN: None     Source Type: Journal    
DOI: 10.1021/la9506842     Document Type: Article
Times cited : (137)

References (73)
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    • note
    • We have studied a variety of nucleophilic displacements including those using sodium azide, sodium thiocyanate, imidazole, triethyl phosphite, and thiazolidinecarboxylic acid. DMF seems to be the solvent of choice on the basis of reagent solubility, anion nucleophilicity, and effective monolayer surface wetting. There is some evidence that increasing the water content of the DMF can reduce its ability to wet the substrate surface and thereby slow down the desired nucleophilic displacement.
  • 52
    • 3743134429 scopus 로고    scopus 로고
    • note
    • We gratefully acknowledge the assistance of Dr. Connie Johns, now of Shaman Pharmaceutical, for the acquisition of this XPS spectrum.
  • 53
    • 3743088556 scopus 로고    scopus 로고
    • note
    • H2 reaction with solution phase ditin species by the intermediate monolayer-bound alkyl radical. Both the substantial steric effect of neighboring trimethyltin substituents and the solution phase concentrations favor hydrogen atom abstraction over homolytic stannylation.
  • 54
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    • Bartlett, P. A. Tetrahedron 1980, 36, 2-72. Leitereg, T. J.; Cram, D. J. J. Am. Chem. Soc. 1968, 90, 4019-4026. Cram, D. J.; Kopecky, K. R. J. Am. Chem. Soc. 1959, 81, 2748-2755. Cram, D. J.; Elhafez, F. A. A. J. Am. Chem. Soc. 1952, 74, 5828-5835.
    • (1980) Tetrahedron , vol.36 , pp. 2-72
    • Bartlett, P.A.1
  • 55
    • 0001538450 scopus 로고
    • Bartlett, P. A. Tetrahedron 1980, 36, 2-72. Leitereg, T. J.; Cram, D. J. J. Am. Chem. Soc. 1968, 90, 4019-4026. Cram, D. J.; Kopecky, K. R. J. Am. Chem. Soc. 1959, 81, 2748-2755. Cram, D. J.; Elhafez, F. A. A. J. Am. Chem. Soc. 1952, 74, 5828-5835.
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 4019-4026
    • Leitereg, T.J.1    Cram, D.J.2
  • 56
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    • Bartlett, P. A. Tetrahedron 1980, 36, 2-72. Leitereg, T. J.; Cram, D. J. J. Am. Chem. Soc. 1968, 90, 4019-4026. Cram, D. J.; Kopecky, K. R. J. Am. Chem. Soc. 1959, 81, 2748-2755. Cram, D. J.; Elhafez, F. A. A. J. Am. Chem. Soc. 1952, 74, 5828-5835.
    • (1959) J. Am. Chem. Soc. , vol.81 , pp. 2748-2755
    • Cram, D.J.1    Kopecky, K.R.2
  • 57
    • 33947569274 scopus 로고
    • Bartlett, P. A. Tetrahedron 1980, 36, 2-72. Leitereg, T. J.; Cram, D. J. J. Am. Chem. Soc. 1968, 90, 4019-4026. Cram, D. J.; Kopecky, K. R. J. Am. Chem. Soc. 1959, 81, 2748-2755. Cram, D. J.; Elhafez, F. A. A. J. Am. Chem. Soc. 1952, 74, 5828-5835.
    • (1952) J. Am. Chem. Soc. , vol.74 , pp. 5828-5835
    • Cram, D.J.1    Elhafez, F.A.A.2
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    • Porter, M. D.; Bright, T. B.; Allara, D. L.; Chidsey, A. E. D. J. Am. Chem. Soc. 1987, 109 , 3559. Bain, C. D.; Troughton, E. B.; Tao, Y. T.; Evall, J.; Whiteside, G. M.; Nuzzo, R. G. J. Am. Chem. Soc. 1989, 111, 321. Netzer, L.; Iscovici, R.; Sagiv, J. Thin Solid Films 1983, 100, 67.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 3559
    • Porter, M.D.1    Bright, T.B.2    Allara, D.L.3    Chidsey, A.E.D.4
  • 60
    • 0021094396 scopus 로고
    • Porter, M. D.; Bright, T. B.; Allara, D. L.; Chidsey, A. E. D. J. Am. Chem. Soc. 1987, 109 , 3559. Bain, C. D.; Troughton, E. B.; Tao, Y. T.; Evall, J.; Whiteside, G. M.; Nuzzo, R. G. J. Am. Chem. Soc. 1989, 111, 321. Netzer, L.; Iscovici, R.; Sagiv, J. Thin Solid Films 1983, 100, 67.
    • (1983) Thin Solid Films , vol.100 , pp. 67
    • Netzer, L.1    Iscovici, R.2    Sagiv, J.3
  • 61
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    • note
    • The solvents tested included acetonitrile, nitromethane, cyclohexane, THF, diethyl ether, acetone, DMF, toluene, triethylamine, pyridine, dichloromethane, and chloroform.
  • 64
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    • Fryxell, G. E.; Linehan, J. C.; Rieke, P. C.; Coffey, G. To be reported separately
    • Fryxell, G. E.; Linehan, J. C.; Rieke, P. C.; Coffey, G. To be reported separately.
  • 66
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    • note
    • It has been reported that these esters were partially hydrolyzed by treatment with concentrated hydrochloric acid, but we had difficulty reproducing this (see ref 59).
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    • Menger, F. M. Acc. Chem. Res. 1985, 18, 128-134. Menger, F. M.; Venkataram, U. V. J. Am. Chem. Soc. 1985, 107, 4706-4709.
    • (1985) Acc. Chem. Res. , vol.18 , pp. 128-134
    • Menger, F.M.1


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