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Hydrogen is a chemical element with an atomic number of 1. It has one proton and one electron. Deuterium is the heavier naturally-occurring stable isotope of hydrogen. Deuterium was discovered by Harold Urey in 1931, for which he received the Nobel Prize in 1934.
Hydrogen–deuterium exchange (also called H–D or H/D exchange) is a chemical reaction in which a covalently bonded hydrogen atom is replaced by a deuterium atom, or vice versa. It can be applied most easily to exchangeable protons and deuterons, where such a transformation occurs in the presence of a suitable deuterium source, without any ...
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 ...
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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 benzene will undergo all the same reactions its normal analogue will, just a little more slowly due to the kinetic isotope effect. For example, deuterated benzene could be used in the synthesis of deuterated benzoic acid , if desired:
Deuterium NMR has a range of chemical shift similar to proton NMR but with poor resolution, due to the smaller magnitude of the magnetic dipole moment of the deuteron relative to the proton. It may be used to verify the effectiveness of deuteration: a deuterated compound will show a strong peak in 2 H NMR but not proton NMR.
In carbon-13 NMR spectroscopy, the sole carbon in deuterated chloroform shows a triplet at a chemical shift of 77.16 ppm with the three peaks being about equal size, resulting from splitting by spin coupling to the attached spin-1 deuterium atom (CHCl 3 has a chemical shift of 77.36 ppm). [4]