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Literature DB >> 23806055

Structure determination using the method of continuous variation: lithium phenolates solvated by protic and dipolar aprotic ligands.

Abstract

The method of continuous variation (MCV) was used in conjunction with (6)Li NMR spectroscopy to characterize four lithium phenolates solvated by a range of solvents, including N,N,N',N'-tetramethylethylenediamine, Et2O, pyridine, protic amines, alcohols, and highly dipolar aprotic solvents. Dimers, trimers, and tetramers were observed, depending on the precise lithium phenolate-solvent combinations. Competition experiments (solvent swaps) provide insights into the relative propensities toward mixed solvation.

Entities: Chemical Disease

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Year: 2013 PMID： 23806055 PMCID： PMC3759316 DOI： 10.1021/jo401080n

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

31 in total

1. 6Li and (15)N NMR Data as a Probe for the Influence of Solvent and Intramolecular Solvation on the Solution-State Structures of Chiral Lithium Amides The authors are most grateful to the Swedish Natural Science Research Council and Carl Trygger for financial support.

Authors:
Journal: Angew Chem Int Ed Engl Date: 2000-04 Impact factor: 15.336

2. Lithium and Cesium Ion-Pair Acidities of Dibenzyl Ketone. Aggregation of Lithium and Cesium Ion Pairs of the Enolate Ion and Dianion(1)(,).

Authors: Roustam Gareyev; James C. Ciula; Andrew Streitwieser
Journal: J Org Chem Date: 1996-07-12 Impact factor: 4.354

3. The regioselectivity of addition of organolithium reagents to enones and enals: the role of HMPA.

Authors: W H Sikorski; H J Reich
Journal: J Am Chem Soc Date: 2001-07-11 Impact factor: 15.419

4. What's going on with these lithium reagents?

Authors: Hans J Reich
Journal: J Org Chem Date: 2012-06-14 Impact factor: 4.354

5. Structure and reactivity of mixed alkali metal alkoxide/aryloxide catalysts.

Authors: R M Kissling; M R Gagné
Journal: J Org Chem Date: 2001-12-28 Impact factor: 4.354

6. Determination of binding stoichiometry by the continuous variation method: the Job plot.

Authors: C Y Huang
Journal: Methods Enzymol Date: 1982 Impact factor: 1.600

Review 7. Modern aldol methods for the total synthesis of polyketides.

Authors: Bernd Schetter; Rainer Mahrwald
Journal: Angew Chem Int Ed Engl Date: 2006-11-20 Impact factor: 15.336

Review 8. Perspectives on computational organic chemistry.

Authors: Andrew Streitwieser
Journal: J Org Chem Date: 2009-06-19 Impact factor: 4.354

9. Microsolvation and 13C-Li NMR coupling.

Authors: Rudolf Knorr; Thomas Menke; Kathrin Ferchland; Johann Mehlstäubl; David S Stephenson
Journal: J Am Chem Soc Date: 2008-10-02 Impact factor: 15.419

10. Structures of beta-amino ester enolates: new strategies using the method of continuous variation.

Authors: Lara R Liou; Anne J McNeil; Gilman E S Toombes; David B Collum
Journal: J Am Chem Soc Date: 2008-12-24 Impact factor: 15.419

8 in total

1. Evans Enolates: Solution Structures of Lithiated Oxazolidinone-Derived Enolates.

Authors: Evan H Tallmadge; David B Collum
Journal: J Am Chem Soc Date: 2015-10-05 Impact factor: 15.419

2. Ligand effects on coordination properties of organolithium compounds: insights from computational experiments on a "weakened" Li^.

Authors: Hélène Gérard; Patrick Chaquin; Jacques Maddaluno
Journal: J Mol Model Date: 2020-02-13 Impact factor: 1.810

Structure determination using the method of continuous variation: lithium phenolates solvated by protic and dipolar aprotic ligands.

1. 6Li and (15)N NMR Data as a Probe for the Influence of Solvent and Intramolecular Solvation on the Solution-State Structures of Chiral Lithium Amides The authors are most grateful to the Swedish Natural Science Research Council and Carl Trygger for financial support.

2. Lithium and Cesium Ion-Pair Acidities of Dibenzyl Ketone. Aggregation of Lithium and Cesium Ion Pairs of the Enolate Ion and Dianion(1)(,).

3. The regioselectivity of addition of organolithium reagents to enones and enals: the role of HMPA.

4. What's going on with these lithium reagents?

5. Structure and reactivity of mixed alkali metal alkoxide/aryloxide catalysts.

6. Determination of binding stoichiometry by the continuous variation method: the Job plot.

Review 7. Modern aldol methods for the total synthesis of polyketides.

Review 8. Perspectives on computational organic chemistry.

9. Microsolvation and 13C-Li NMR coupling.

10. Structures of beta-amino ester enolates: new strategies using the method of continuous variation.

1. Evans Enolates: Solution Structures of Lithiated Oxazolidinone-Derived Enolates.

2. Ligand effects on coordination properties of organolithium compounds: insights from computational experiments on a "weakened" Li^.

3. Aryl Carbamates: Mechanisms of Orthosodiations and Snieckus-Fries Rearrangements.

4. Lithium Enolates Derived from Pyroglutaminol: Aggregation, Solvation, and Atropisomerism.

5. Solid-State and Solution Structures of Glycinimine-Derived Lithium Enolates.

6. Solution structures of lithium amino alkoxides used in highly enantioselective 1,2-additions.

7. Method of continuous variation: characterization of alkali metal enolates using ¹H and ¹⁹F NMR spectroscopies.

Review 8. My maize and blue brick road to physical organic chemistry in materials.