Lithium imide

Last updated
Lithium imide
Lithium imide.png
CaF2 polyhedra.png
__ Li +     __ NH 2−
Names
IUPAC name
Lithium imide
Identifiers
3D model (JSmol)
  • Key: LWEQKNGYZUCTTC-UHFFFAOYSA-N
  • InChI=1S/2Li.HN/h;;1H/q2*+1;-2
  • [Li+].[Li+].[NH-2]
Properties
Li2NH
Molar mass 28.897 g/mol
Density 1.48 g/cm3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Lithium imide is an inorganic compound with the chemical formula Li2NH. This white solid can be formed by a reaction between lithium amide and lithium hydride. [1]

LiNH2 + LiH → Li2NH + H2

The product is light-sensitive and can undergo disproportionation to form lithium nitride, which is characteristically red.

2 Li2NH → LiNH2 + Li3N

Lithium imide is thought to have a simple face-centered cubic structure with a Fm3m space group; with N-H bond distances of 0.82(6) Å and a H–N–H bond angle of 109.5°, giving it a similar structure to lithium amide. [2] [3]

Lithium imide is strongly basic and deprotonates even some extremely weak acids such as methane and ammonia, due to the very localized negative charge on the nitrogen, which carries two formal charges. It has uses in organic and organometallic chemistry. It has been investigated as a material for hydrogen storage. [1]

Related Research Articles

Alkali metal Group of highly-reactive chemical elements

The alkali metals consist of the chemical elements lithium (Li), sodium (Na), potassium (K), rubidium (Rb), caesium (Cs), and francium (Fr). Together with hydrogen they constitute group 1, which lies in the s-block of the periodic table. All alkali metals have their outermost electron in an s-orbital: this shared electron configuration results in their having very similar characteristic properties. Indeed, the alkali metals provide the best example of group trends in properties in the periodic table, with elements exhibiting well-characterised homologous behaviour. This family of elements is also known as the lithium family after its leading element.

Amide Chemical compound

In organic chemistry, an amide ( or or, also known as an organic amide or a carboxamide, is a compound with the general formula RC NR′R″, where R, R', and R″ represent organic groups or hydrogen atoms. The amide group is called a peptide bond when it is part of the main chain of a protein, and an isopeptide bond when it occurs in a side chain, such as in the amino acids asparagine and glutamine. It can be viewed as a derivative of a carboxylic acid RC OH with the hydroxyl group –OH replaced by an amine group −NR′R″; or, equivalently, an acyl group RC − joined to an amine group.

Hydroxide Chemical compound

Hydroxide is a diatomic anion with chemical formula OH. It consists of an oxygen and hydrogen atom held together by a single covalent bond, and carries a negative electric charge. It is an important but usually minor constituent of water. It functions as a base, a ligand, a nucleophile, and a catalyst. The hydroxide ion forms salts, some of which dissociate in aqueous solution, liberating solvated hydroxide ions. Sodium hydroxide is a multi-million-ton per annum commodity chemical. The corresponding electrically neutral compound HO is the hydroxyl radical. The corresponding covalently bound group –OH of atoms is the hydroxy group. Both the hydroxide ion and hydroxy group are nucleophiles and can act as catalysts in organic chemistry.

Lithium aluminium hydride Chemical compound

Lithium aluminium hydride, commonly abbreviated to LAH, is an inorganic compound with the chemical formula LiAlH4. It is a white solid, discovered by Finholt, Bond and Schlesinger in 1947. This compound is used as a reducing agent in organic synthesis, especially for the reduction of esters, carboxylic acids, and amides. The solid is dangerously reactive toward water, releasing gaseous hydrogen (H2). Some related derivatives have been discussed for hydrogen storage.

Organolithium reagent

Organolithium reagents are organometallic compounds that contain carbon–lithium bonds. These reagents are important in organic synthesis, and are frequently used to transfer the organic group or the lithium atom to the substrates in synthetic steps, through nucleophilic addition or simple deprotonation. Organolithium reagents are used in industry as an initiator for anionic polymerization, which leads to the production of various elastomers. They have also been applied in asymmetric synthesis in the pharmaceutical industry. Due to the large difference in electronegativity between the carbon atom and the lithium atom, the C−Li bond is highly ionic. Owing to the polar nature of the C−Li bond, organolithium reagents are good nucleophiles and strong bases. For laboratory organic synthesis, many organolithium reagents are commercially available in solution form. These reagents are highly reactive, and are sometimes pyrophoric.

Europium(III) chloride Chemical compound

Europium(III) chloride is an inorganic compound with the formula EuCl3. The anhydrous compound is a yellow solid. Being hygroscopic it rapidly absorbs water to form a white crystalline hexahydrate, EuCl3·6H2O, which is colourless. The compound is used in research.

In organometallic chemistry, acetylide refers to chemical compounds with the chemical formulas MC≡CH and MC≡CM, where M is a metal. The term is used loosely and can refer to substituted acetylides having the general structure RC−CM. Acetylides are reagents in organic synthesis. The calcium acetylide commonly called calcium carbide is a major compound of commerce.

Lithium nitride Chemical compound

Lithium nitride is a compound with the formula Li3N. It is the only stable alkali metal nitride. The solid has a reddish-pink color and high melting point.

Tetrasulfur tetranitride Chemical compound

Tetrasulfur tetranitride is an inorganic compound with the formula S4N4. This gold-poppy coloured solid is the most important binary sulfur nitride, which are compounds that contain only the elements sulfur and nitrogen. It is a precursor to many S-N compounds and has attracted wide interest for its unusual structure and bonding.

Ammonia borane Chemical compound

Ammonia borane (also systematically named amminetrihydridoboron), also called borazane, is the chemical compound with the formula H3NBH3. The colourless or white solid is the simplest molecular boron-nitrogen-hydride compound. It has attracted attention as a source of hydrogen fuel, but is otherwise primarily of academic interest.

Lithium amide Chemical compound

Lithium amide or lithium azanide is an inorganic compound with the chemical formula LiNH2. It is a white solid with a tetragonal crystal structure. Lithium amide can be made by treating lithium metal with liquid ammonia:

Bis(trimethylsilyl)amine (also known as hexamethyldisilazane and HMDS) is an organosilicon compound with the molecular formula [(CH3)3Si]2NH. The molecule is a derivative of ammonia with trimethylsilyl groups in place of two hydrogen atoms. An electron diffraction study shows that silicon-nitrogen bond length (173.5 pm) and Si-N-Si bond angle (125.5°) to be similar to disilazane (in which methyl groups are replaced by hydrogen atoms) suggesting that steric factors are not a factor in regulating angles in this case. This colorless liquid is a reagent and a precursor to bases that are popular in organic synthesis and organometallic chemistry. Additionally, HMDS is also increasingly used as molecular precursor in chemical vapor deposition techniques to deposit silicon carbonitride thin films or coatings.

Lithium bis(trimethylsilyl)amide Chemical compound

Lithium bis(trimethylsilyl)amide is a lithiated organosilicon compound with the formula LiN(Si 3)2. It is commonly abbreviated as LiHMDS and is primarily used as a strong non-nucleophilic base and as a ligand. Like many lithium reagents, it has a tendency to aggregate and will form a cyclic trimer in the absence of coordinating species.

Lithium superoxide is an unstable inorganic salt with formula LiO2. A radical compound, it can be produced at low temperature in matrix isolation experiments, or in certain nonpolar, non-protic solvents. Lithium superoxide is also a transient species during the reduction of oxygen in a lithium–air galvanic cell, and serves as a main constraint on possible solvents for such a battery. For this reason, it has been investigated thoroughly using a variety of methods, both theoretical and spectroscopic.

Magnesium hydride Chemical compound

Magnesium hydride is the chemical compound with the molecular formula MgH2. It contains 7.66% by weight of hydrogen and has been studied as a potential hydrogen storage medium.

Metal amides

Metal amides (systematic name metal azanides) are a class of coordination compounds composed of a metal center with amide ligands of the form NR2. Amide ligands have two electron pairs available for bonding. In principle, they can be terminal or bridging. In these two examples, the dimethylamido ligands are both bridging and terminal:

William I. F. David

William I. F. David FRS is a professor of Materials Chemistry in the Department of Chemistry at the University of Oxford, an STFC Senior Fellow at the ISIS neutron source at the Rutherford Appleton Laboratory and a Fellow of St Catherine's College, Oxford.

A hydridonitride is a chemical compound that contains hydride and nitride ions in a single phase. These inorganic compounds are distinct from inorganic amides and imides as the hydrogen does not share a bond with nitrogen, and contain a larger proportion of metals.

The inorganic imides are compounds containing an ion composed of nitrogen bonded to hydrogen with formula HN2−. Organic imides have the NH group, and two single or one double covalent bond to other atoms. The imides are related to the inorganic amides (H2N), the nitrides (N3−) and the nitridohydrides (N3−•H).

Nitrogen pentahydride Chemical compound

Nitrogen pentahydride, also known as ammonium hydride is a hypothetical compound with the chemical formula NH5. There are two theoretical structures of nitrogen pentahydride. One structure is trigonal bipyramidal molecular geometry type NH5 molecule. Its nitrogen atom and hydrogen atoms are covalently bounded, and its symmetry group is D3h. Another predicted structure of nitrogen pentahydride is an ionic compound, make up of an ammonium ion and a hydride ion (NH4+H). Until now, no one has synthesized this substance, or proved its existence, and related experiments have not directly observed nitrogen pentahydride. It is only speculated that it may be a reactive intermediate based on reaction products. Theoretical calculations show this molecule is thermodynamically unstable. The reason might be similar to the instability of nitrogen pentafluoride, so the possibility of its existence is low. However, nitrogen pentahydride might exist in special conditions or high pressure. Nitrogen pentahydride was considered for use as a solid rocket fuel for research in 1966.

References

  1. 1 2 Ichikawa, Takayuki; Hanada, Nobuko; Isobe, Shigehito; Leng, Haiyan; Fujii, Hironobu (June 2004). "Mechanism of Novel Reaction from LiNH2 and LiH to Li2NH and H2 as a Promising Hydrogen Storage System". The Journal of Physical Chemistry B. 108 (23): 7887–7892. doi:10.1021/jp049968y.
  2. Ohoyama, Kenji; Nakamori, Yuko; Orimo, Shin-ichi; Yamada, Kazuyoshi (15 January 2005). "Revised Crystal Structure Model of Li2NH by Neutron Powder Diffraction". Journal of the Physical Society of Japan. 74 (1): 483–487. arXiv: cond-mat/0406025 . Bibcode:2005JPSJ...74..483O. doi:10.1143/JPSJ.74.483. S2CID   94983390.
  3. Noritake, T.; Nozaki, H.; Aoki, M.; Towata, S.; Kitahara, G.; Nakamori, Y.; Orimo, S. (May 2005). "Crystal structure and charge density analysis of Li2NH by synchrotron X-ray diffraction". Journal of Alloys and Compounds. 393 (1–2): 264–268. doi:10.1016/j.jallcom.2004.09.063.