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The enthalpy of formation Δ f H 0 of tetra-n-butylammonium iodide is −499 kJ/mol, which is lower than that for the bromide or chloride (−540, −564 kJ/mol). [2] At lower temperatures with water tetra-n-butylammonium iodide forms a clathrate hydrate. [2] The tetra-n-butylammonium cation is large and hydrophobic.
Butyl iodide (1-iodobutane) is an organic compound which is an iodo derivative of butane. It is used as an alkylating agent. Isomer.
tetrabutylammonium iodide, a low cost catalyst. [1] tetrabutylammonium triiodide, a common carrier of the triiodide anion used in chemical synthesis. tetrabutylammonium hydroxide, a precursor to other tetrabutylammonium salts via acid-base reactions. tetrabutylammonium hexafluorophosphate, an electrolyte for nonaqueous electrochemistry.
The effect of the tert-butyl group on the progress of a chemical reaction is called the Thorpe–Ingold effect illustrated in the Diels-Alder reaction below. Compared to a hydrogen substituent, the tert-butyl substituent accelerates the reaction rate by a factor of 240. [2] tert-Butyl effect. The tert-butyl effect is an example of steric hindrance.
tert-Butyloxycarbonyl protecting group. The tert-butyloxycarbonyl protecting group or tert-butoxycarbonyl protecting group [1] (BOC group) is an acid-labile protecting group used in organic synthesis. The BOC group can be added to amines under aqueous conditions using di-tert-butyl dicarbonate in the presence of a base such as sodium hydroxide:
tert-Butyllithium and sec-butyllithium are generally more reactive and have better selectivity than n-butyllithium, however, they are also more expensive and difficult to handle. [47] Metalation is a common way of preparing versatile organolithium reagents. The position of metalation is mostly controlled by the acidity of the C-H bond ...
Steric hindrance prevents the activation of tert-butyl iodide by Dostál's bismuthinidene, although a metastable analog with amine pincer arms rather than imine pincer arms (Ar'Bi, where Ar' = 2,6-C 6 H 3 (CH 2 NMe 2) 2) does participate in oxidative addition even with bulky tertiary C-X bonds, likely because the increased rotational mobility ...
However, if an unreactive alkylating agent is used (e.g. an alkyl chloride) then the rate of reaction can be greatly improved by the addition of a catalytic quantity of a soluble iodide salt (which undergoes halide exchange with the chloride to yield a much more reactive iodide, a variant of the Finkelstein reaction).