Sodium hydride is the chemical compound with the system NaH. It is on the whole used as a robust base in natural synthesis. NaH is a consultant of the saline hydrides, which means it's miles a salt-like hydride, composed of Na+ and H− ions, in evaluation to the greater molecular hydrides which include borane, methane, ammonia, and water. It is an ionic cloth this is insoluble in natural solvents (despite the fact that seemingly soluble in molten Na), constant with the truth that H− stays an unknown anion in solution. Because of the insolubility of NaH, all reactions related to NaH arise on the floor of the strong.
Basic residences and structure
NaH is produced with the aid of using the direct response of hydrogen and liquid sodium.[1] Pure NaH is colorless, despite the fact that samples commonly seem gray. NaH is ca. 40 nser than Na (0.968 g/cm³)?
NaH, like LiH, KH, RbH, and CsH, adopts the NaCl crystal structure. In this motif, every Na+ ion is surrounded with the aid of using six H− facilities in an octahedral geometry. The ionic radii of H− (146 pm in NaH) and F− (133 pm) are comparable, as judged with the aid of using the Na−H and Na−F distances.[2]
Applications in natural synthesis
First and foremost, NaH is a base of huge scope and software in natural chemistry.[3] It is able to deprotonate a huge variety of even vulnerable Brønsted acids to offer the corresponding sodium derivatives. Typical "easy" substrates incorporate O-H, N-H, and S-H bonds, which include alcohols, phenols, pyrazoles, and thiols.
NaH maximum appreciably is hired to deprotonate carbon acids which include 1,3-dicarbonyls and analogs which include malonic esters. The ensuing sodium derivatives may be alkylated. NaH is broadly used to sell condensation reactions of carbonyl compounds through the Dieckmann condensation, Stobbe condensation, Darzens condensation, and Claisen condensation. Other carbon acids at risk of deprotonation with the aid of using NaH consist of sulfonium salts and DMSO.
In an illustrative response, NaH is used to make sulfur ylides, which in flip are used to transform ketones into epoxides. Also, it's miles utilized in one synthesis of the dithioimidodi phosphinates which might be an exciting elegance of acacia-like ligands in inorganic chemistry.
NaH reduces Si-Si and S-S bonds in disilanes and disulfides. Otherwise, NaH not often well-known shows the lowering traits of Na itself.
Practical considerations
Sodium hydride is bought with the aid of using many chemical providers which include Sigma-Aldrich and ACROS, generally as an aggregate of 60% sodium hydride (w/w) in mineral oil. Such a dispersion is more secure to address and weigh than natural NaH. The natural white strong is ready with the aid of using rinsing the oil with pentane or THF, care being taken that the washings will incorporate lines of NaH that may ignite withinside the air. Reactions related to NaH require an inert atmosphere, which includes nitrogen gas. Typically NaH is used as a suspension in THF; THF resists deprotonation but solvates many natural sodium compounds.
Safety
NaH can ignite withinside the air, specifically upon touch with water. The response offers off hydrogen, in all likelihood explosively. Hydrolysis converts NaH into sodium hydroxide (NaOH), a caustic base.
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