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Relevant academic research and scientific papers

Cobalt-Catalyzed Stereoretentive Hydrogen Isotope Exchange of C(sp3)-H Bonds

Cobalt dialkyl complexes bearing α-diimine ligands proved to be active precatalysts for the nondirected, C(sp3)-H selective hydrogen isotope exchange (HIE) of alkylarenes using D2 gas as the deuterium source. Alkylarenes with a variety of substitution patterns and heteroatom substituents on the arene ring were successfully labeled, enabling high levels of incorporation into primary, secondary, and tertiary benzylic C(sp3)-H bonds. In some cases, the HIE proceeded with high diastereoselectivity and application of the cobalt-catalyzed method to enantioenriched substrates with benzylic stereocenters provided enantioretentive hydrogen isotope exchange at tertiary carbons.

Secondary alpha isotope effects on deuterium tunneling in triplet o-methylanthrones: Extraordinary sensitivity to barrier width

The rates of deuterium transfer in the photoenolization of triplet 1,4-dimethyl-10H-anthracen-9-one (1) with varying degrees of deuterium label in their methyl groups (1-d3, 1-d2, and 1-d) have been investigated as a function of temperature between 5 and 77 K. Measurable rate constants in the case of 1-d3 and 1-d2 were used to construct Arrhenius plots which illustrate the expected curvature and leveling off of rate constant versus temperature. The difference in tunneling rate constants of 1-d3 and 1-d2 yields a tunneling isotope effect, TIE = 2.4, which is attributed to the secondary alpha isotopic substitution. Density functional theory (DFT, B3LYP/6-31G*) calculations were carried out to obtain structural and energetic information for the H(D) transfer along the triplet state zero-point energy levels. The temperature dependence of the rate constants for each isotopologue was simulated with a model that considers the frequency of the C-D stretching mode and the quantum mechanical permeability determined from calculated energy parameters. The model suggests that a difference in barrier width of only 0.015 A between 1-d3 and 1-d2 leads to the observed 2-fold difference between tunneling rates. Copyright

Chemical pressure effect by selective deuteration in the molecular-based conductor, 2,5-dimethyl-N,N'-dicyano-p-benzoquinone immine-copper salt, (DMe-DCNQI)2Cu

The mixed-valence copper salt of DMe-DCNQI91, where DMe-DCNQI=2,5-dimethyl-N,N'-dicyano-p-benzoquinone diimine) is a molecular conductor whose electrical and magnetic properties are quite sensitive to pressure.We have performed selective deuteriation of the molecule 1.By control of the position and number of deuterium atoms, the low-pressure region (ca. 500 bar) in the pressure-temperature phase diagram of (1)2Cu was reproduced at ambient pressure.The equivalency of the deuteriation and pressure effects is explained from steric origins; 'contraction' aroused by the slightly shorter C-D bond (steric isotope effect) and 'constriction' by pressure.