Factors in Aldol Condensations of Alkyl Acetates with Benzophenone and Reversals by Sodium Amide Versus Lithium Amide. Metallic Cation Effects1

1960 ◽  
Vol 25 (8) ◽  
pp. 1296-1302 ◽  
Author(s):  
CHARLES R. HAUSER ◽  
WILLIAM R. DUNNAVANT
Keyword(s):  
Lithium Amide ◽  
Metallic Cation ◽  
Alkyl Acetates ◽  
Amide Versus ◽  
Sodium Amide

scholarly journals Benchmarking lithium amide versus amine bonding by charge density and energy decomposition analysis arguments

2018 ◽  
Vol 9 (12) ◽  
pp. 3111-3121 ◽  
Author(s):  
Felix Engelhardt ◽  
Christian Maaß ◽  
Diego M. Andrada ◽  
Regine Herbst-Irmer ◽  
Dietmar Stalke
Keyword(s):  
Quantum Theory ◽  
Dft Calculations ◽  
Charge Density ◽  
Decomposition Analysis ◽  
Atoms In Molecules ◽  
Energy Decomposition Analysis ◽  
Energy Decomposition ◽  
Lithium Amide ◽  
Experimental Charge Density ◽  
Amide Versus

We investigated [{(Me2NCH2)2(C4H2N)}Li]2 (1) by means of experimental charge density calculations based on the quantum theory of atoms in molecules (QTAIM) and DFT calculations using energy decomposition analysis (EDA).

Condensation of Alkyl Acetates with Benzophenone by Lithium Amide to Form β-Hydroxy Esters. Relative Ease of Self-condensation of Esters1

1960 ◽  
Vol 25 (10) ◽  
pp. 1693-1699 ◽  
Author(s):  
WILLIAM R. DUNNAVANT ◽  
CHARLES R. HAUSER
Keyword(s):  
Lithium Amide ◽  
Relative Ease ◽  
Hydroxy Esters ◽  
Alkyl Acetates

Sur quelques réactions acide-base dans les solvants fortement basiques anhydres. II. Les amino-2 éthylamidures de sodium et de potassium

1969 ◽  
Vol 47 (19) ◽  
pp. 3509-3513 ◽  
Author(s):  
W. R. Heumann ◽  
A. Bouchard ◽  
L. Šafařík
Keyword(s):  
Hydrochloric Acid ◽  
Solid Product ◽  
Pure Nitrogen ◽  
Lithium Amide ◽  
Potassium Hydride ◽  
Basic Strength ◽  
Sodium Amide

Solutions of sodium 2-aminoethylamide in anhydrous ethylenediamine were prepared by dissolving ammoniacal sodium amide NaNH2 in ethylenediamine and removing the ammonia formed in vacuum. When these solutions were prepared and kept under nitrogen containing not more than about 5 p.p.m. of oxygen and 1 p.p.m. of moisture, they remained colorless and stable. Upon addition of benzene to these solutions, the pure amide precipitated as fine greyish–white crystals, which were also stable under pure nitrogen. The potassium 2-aminoethylamide was prepared in a similar way from ethylenediamine and potassium hydride. Its solid product resembles that of the corresponding sodium amide, but its solutions in ethylenediamine are less stable, rapidly turning dark brown because of polymerization. The basic strengths of these two 2-aminoethylamides were compared with the corresponding lithium amide by following potentiometrically the neutralization of ethylenediamine solutions of hydrochloric acid, p-methoxyphenol, water, and ethanolamine respectively. According to the heights of the potential jumps at the equivalence points the basic strength of the amides was found to increase in the order Na < Li < K.

ChemInform Abstract: TRILITHIUM SODIUM AMIDE (LI3NA(NH2)4), A COMPOUND WITH A STRUCTURE RELATED TO LITHIUM AMIDE

1982 ◽  
Vol 13 (44) ◽  
Author(s):  
H. JACOBS ◽  
B. HARBRECHT
Keyword(s):  
Lithium Amide ◽  
Sodium Amide

Mixed aggregates: crystal structures of a lithium ketone enolate/lithium amide and of a sodium ester enolate/sodium amide

1990 ◽  
Vol 112 (23) ◽  
pp. 8602-8604 ◽  
Author(s):  
Paul G. Williard ◽  
Mark J. Hintze
Keyword(s):  
Crystal Structures ◽  
Lithium Amide ◽  
Mixed Aggregates ◽  
Ester Enolate ◽  
Sodium Amide

scholarly journals Lithium-mediated Ferration of Fluoroarenes

2020 ◽  
Vol 74 (11) ◽  
pp. 866-870
Author(s):  
Lewis C. H. Maddock ◽  
Alan Kennedy ◽  
Eva Hevia
Keyword(s):  
Hydrogen Atom ◽  
Organometallic Chemistry ◽  
Room Temperature ◽  
Structural Elucidation ◽  
Side Reactions ◽  
Metal Base ◽  
Lithium Amide ◽  
Mixed Metal ◽  
Important Challenge

While fluoroaryl fragments are ubiquitous in many pharmaceuticals, the deprotonation of fluoroarenes using organolithium bases constitutes an important challenge in polar organometallic chemistry. This has been widely attributed to the low stability of the in situ generated aryl lithium intermediates that even at –78 °C can undergo unwanted side reactions. Herein, pairing lithium amide LiHMDS (HMDS = N{SiMe3}2) with FeII(HMDS)2 enables the selective deprotonation at room temperature of pentafluorobenzene and 1,3,5-trifluorobenzene via the mixed-metal base [(dioxane)LiFe(HMDS)3] (1) (dioxane = 1,4-dioxane). Structural elucidation of the organometallic intermediates [(dioxane)Li(HMDS)2Fe(ArF)] (ArF = C6F5, 2; 1,3,5-F3-C6H2, 3) prior electrophilic interception demonstrates that these deprotonations are actually ferrations, with Fe occupying the position previously filled by a hydrogen atom. Notwithstanding, the presence of lithium is essential for the reactions to take place as Fe II (HMDS)2 on its own is completely inert towards the metallation of these substrates. Interestingly 2 and 3 are thermally stable and they do not undergo benzyne formation via LiF elimination.

The Metalation and Addition Reactions of Allylbenzene and Propenylbenzene with Butyllithium and Lithium Amide

1957 ◽  
Vol 79 (21) ◽  
pp. 5809-5814 ◽  
Author(s):  
Harry F. Herbrandson ◽  
David S. Mooney
Keyword(s):  
Addition Reactions ◽  
Lithium Amide

scholarly journals Compositional flexibility in Li-N-H materials: implications for ammonia catalysis and hydrogen storage.

2021 ◽  
Author(s):  
Joshua Makepeace ◽  
Jake M Brittain ◽  
Alisha Sukhwani Manghnani ◽  
Claire Murray ◽  
Thomas J Wood ◽  
...  
Keyword(s):  
Energy Storage ◽  
Hydrogen Storage ◽  
Compositional Variation ◽  
Lithium Amide ◽  
Lithium Imide ◽  
Energy Storage Applications

Li-N-H materials, particularly lithium amide and lithium imide, have been explored for use in a variety of energy storage applications in recent years. Compositional variation within the parent lithium imide,...

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