The preparation of three new partially deuterated hexadecanethiols for applications in surface chemistry

The synthesis of three partially deuterated hexadecanethiols has been achieved. Thiols CH3(CH2)7(CD2)8SH, CD3(CD2)7(CH2)8SH and CD3(CH2)15SH were targeted, as these compounds, after formation of self‐assembled monolayers on Au(1 1 1) or Au nanoparticles, can provide mechanistic information pertainin...

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Bibliographic Details
Published in:Journal of labelled compounds & radiopharmaceuticals 2008-10, Vol.51 (12), p.391-398
Main Authors: Sheepwash, Erin E., Rowntree, Paul A., Schwan, Adrian L.
Format: Article
Language:English
Subjects:
Aliphatic compounds
Chemistry
deuterium
Exact sciences and technology
grignard reaction
Organic chemistry
Preparations and properties
self-assembled monolayers
thiol
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Summary:The synthesis of three partially deuterated hexadecanethiols has been achieved. Thiols CH3(CH2)7(CD2)8SH, CD3(CD2)7(CH2)8SH and CD3(CH2)15SH were targeted, as these compounds, after formation of self‐assembled monolayers on Au(1 1 1) or Au nanoparticles, can provide mechanistic information pertaining to reactive atom migrations within the assembly. The syntheses of each of these compounds called upon Grignard coupling chemistry, which was activated by Li2CuCl4. Applicable deuterium containing fragments were either commercially obtained or constructed from by way of an inexpensive and efficient ring opening, protection and dimerization of THF‐d8. Sulfur incorporation was by thiolacetate substitution or addition reactions. The protocols presented possess general applicability in a number of syntheses requiring block‐deuterated fattyalkyl sections. Copyright © 2008 John Wiley & Sons, Ltd. This paper presents the synthesis of 3 partially deuterated hexadecanethiols to study low‐energy electron‐induced processes in gold‐thiolate self‐assembled monolayers. Synthesis was carried out using Grignard coupling reactions as the principal tool to introduce deuterated fragments into smaller molecules. Copyright © 2008 John Wiley & Sons, Ltd.
ISSN:0362-4803
1099-1344
DOI:10.1002/jlcr.1541