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As the name suggests, a non-nucleophilic base is a sterically hindered organic base that is a poor nucleophile.Normal bases are also nucleophiles, but often chemists seek the proton-removing ability of a base without any other functions.
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This amine is used in chemistry as a hindered base (hindered amine). Although TMP finds limited use per se, its derivatives are a mainstay of hindered amine light stabilizers. TMP is the starting material for an even stronger base, lithium tetramethylpiperidide and the radical species TEMPO. Another non-nucleophilic base is N,N ...
Tetramethylguanidine is mainly used as a strong, non-nucleophilic base for alkylations, often as a substitute for the more expensive DBU and DBN. [3] Since it is highly water-soluble, it is easily removed from mixtures in organic solvents. It is also used as a base-catalyst in the production of polyurethane. [4]
LiHMDS is often used in organic chemistry as a strong non-nucleophilic base. [3] Its conjugate acid has a pK a of ~26, [4] making it is less basic than other lithium bases, such as LDA (pK a of conjugate acid ~36). It is relatively more sterically hindered and hence less nucleophilic than other lithium bases.
N,N-Diisopropylethylamine, or Hünig's base, is an organic compound that is a tertiary amine. It is named after the German chemist Siegfried Hünig . It is used in organic chemistry as a non-nucleophilic base. It is commonly abbreviated as DIPEA, DIEA, or i-Pr 2 NEt.
Lithium diisopropylamide (commonly abbreviated LDA) is a chemical compound with the molecular formula LiN(CH(CH 3) 2) 2.It is used as a strong base and has been widely utilized due to its good solubility in non-polar organic solvents and non-nucleophilic nature.
Bases are defined by the Brønsted–Lowry theory as chemical substances that can accept a proton, i.e., a hydrogen ion.In water this is equivalent to a hydronium ion). The Lewis theory instead defines a Base as an electron-pair donor.