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The concept of replacing hydrogen with deuterium is an example of bioisosterism, whereby similar biological effects to a known drug are produced in an analog designed to confer superior properties. [5] The first patent in the US granted for deuterated molecules was in the 1970s. Since then patents on deuterated drugs have become more common. [6]
For detection by mass spectrometry, the pH is dropped to the minimum of the exchange curve, pH 2.6. In the most basic experiment, the reaction is allowed to take place for a set time before it is quenched. The deuteration pattern of a molecule that has undergone H/D exchange can be maintained in aprotic environments.
Deuterated DMSO is produced by heating DMSO in heavy water (D 2 O) with a basic catalyst such as calcium oxide.The reaction does not give complete conversion to the d 6 product, and the water produced must be removed and replaced with D 2 O several times to drive the equilibrium to the fully deuterated product.
The reaction mechanism of the Mitsunobu reaction is fairly complex. The identity of intermediates and the roles they play has been the subject of debate. Initially, the triphenyl phosphine (2) makes a nucleophilic attack upon diethyl azodicarboxylate (1) producing a betaine intermediate 3, which deprotonates the carboxylic acid (4) to form the ion pair 5.
Deuterated acetone is prepared by the reaction of acetone with heavy water, 2 H 2 O or D 2 O, in the presence of a base. In this case, the base used is deuterated lithium hydroxide : [ 1 ] In order to fully deuterate the acetone, the process is repeated several times, distilling off the acetone from the heavy water, and re-running the reaction ...
For example, deuterated benzene could be used in the synthesis of deuterated benzoic acid, if desired: Many simple monosubstituted aromatic compounds bearing the deuterated phenyl (C 6 D 5 ) group may be purchased commercially, such as aniline , acetophenone , nitrobenzene , bromobenzene , and more.
Deuterated chloroform, also known as chloroform-d, is the organic compound with the formula CDCl 3.Deuterated chloroform is a common solvent used in NMR spectroscopy. [2] The properties of CDCl 3 and ordinary CHCl 3 are virtually identical.
Deuterium NMR is NMR spectroscopy of deuterium (2 H or D), an isotope of hydrogen. [1] Deuterium is an isotope with spin = 1, unlike hydrogen-1, which has spin = 1/2. The term deuteron NMR, in direct analogy to proton NMR, is also used. [2]