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Volumn 131, Issue 36, 2009, Pages 13142-13154

Lithium phenolates solvated by tetrahydrofuran and 1,2-dimethoxyethane: Structure determination using the method of continuous variation

Author keywords

[No Author keywords available]

Indexed keywords

AGGREGATION NUMBERS; COMPUTATIONAL STUDIES; HETERO-AGGREGATES; NMR SPECTROSCOPY; PENTAMERS; STRUCTURE DETERMINATION; TETRA-HYDROFURAN; TETRAMERS;

EID: 70349125054     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9047784     Document Type: Article
Times cited : (37)

References (205)
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    • A number of phenolates in Table 1 have been characterized crystallographically. The coordinating solvent and resulting aggregation states are as follows: (a) 7 (THF), hexamer: Jackman, L. M.; Çizmeciyan, D.; Williard, P. G.; Nichols, M. A. J. Am. Chem. Soc. 1993, 115, 6262.
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    • Jackman observed a putative hexamer in more poorly coordinating solvents (ref 5). β-amino ester enolates are uniformly hexameric in THF (ref 6)
    • Jackman observed a putative hexamer in more poorly coordinating solvents (ref 5). β-amino ester enolates are uniformly hexameric in THF (ref 6).
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    • Although we cannot find evidence of five-rung (pentameric) ladders in the crystallographic literature, we observed them as part of nearly statistical ensembles of 3-, 4-, 5-, and 6-rung lithium diethylamide ladders: Rutherford, J. L.; Collum, D. B. J. Am. Chem. Soc. 1999, 121, 10198.
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    • 2 by parametric fit at very low or very high relative AB concentration. It is ironic, therefore, that the parametric fits become less effective precisely when the deviation from statistical shows the distinction is most needed
    • 2 by parametric fit at very low or very high relative AB concentration. It is ironic, therefore, that the parametric fits become less effective precisely when the deviation from statistical shows the distinction is most needed.
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    • Standard ethereal ligands have been observed coordinated to lithium ion in the slow exchange limit only rarely and only at very low temperatures. Leading references: (a)
    • Standard ethereal ligands have been observed coordinated to lithium ion in the slow exchange limit only rarely and only at very low temperatures. Leading references: (a) Arvidsson, P. I.; Davidsson, Ö. Angew. Chem., Int. Ed. 2000, 39, 1467.
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    • (a) One can infer approximate relative solvent binding constants from the proportions of the two solvents required to achieve a 50% shift. In Figure 9c, for example, the average chemical shift at equimolar THF and DME suggests a preference for the THF-solvated dimer.
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    • Our first experience with solvent swaps occurred during studies of unsolvated lithium diisopropylamide in which addition of a weakly coordinating trialkylamine caused only one of several unsolvated cyclic oligomers to migrate to the chemical shift of the disolvated dimer (ref 34b).
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    • The temperature-dependent change in solvation with warming is inferred to be desolvation because of the substantial negative enthalpies of solvation. For related desolvations, see refs 34 and 53.
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    • The hindered chelating ligand, TMEDA, affords no cyclic trimers (ref 7b)
    • The hindered chelating ligand, TMEDA, affords no cyclic trimers (ref 7b).
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    • Tetrameric ladders are suggested to be of nearly equal stability when compared with the corresponding pentamers (both U-shaped; energy in kcal/mol on a per-lithium basis at -90°C)
    • Tetrameric ladders are suggested to be of nearly equal stability when compared with the corresponding pentamers (both U-shaped; energy in kcal/mol on a per-lithium basis at -90°C).
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    • The tendency for electron-withdrawing groups to promote deaggregation was noted by spectroscopic studies of Jackman and coworkers (ref 5) and has previously been suggested based on combination of computations and crystal structures Henderson and coworkers (ref 40b)
    • The tendency for electron-withdrawing groups to promote deaggregation was noted by spectroscopic studies of Jackman and coworkers (ref 5) and has previously been suggested based on combination of computations and crystal structures Henderson and coworkers (ref 40b).


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