Matches in SemOpenAlex for { <https://semopenalex.org/work/W2022886086> ?p ?o ?g. }
- W2022886086 endingPage "6955" @default.
- W2022886086 startingPage "6944" @default.
- W2022886086 abstract "Single enantiomers of R/S-methylbenzylamine (MBA) were found to selectively form adducts with two chiral Cu–salen complexes, [CuII(1)] (H21 = N,N′-bis(3,5-ditert-butylsalicylidene)-1,2-diaminocyclohexane) and [CuII(2)] (H22 = N,N′-bis-salicylidene-1,2-cyclohexanediamino). The axial g/A spin Hamiltonian parameters of the Cu–MBA adducts were typical of 5-coordinate species. Enantiomer discrimination in the MBA binding was directly evidenced by W-band CW EPR, revealing an 86 ± 5% preference for formation of the R,R-[Cu(1)] + S-MBA adducts compared to R,R-[Cu(1)] + R-MBA; this was reduced to a 57 ± 5% preference for R,R-[Cu(2)] + S-MBA following removal of the tert-butyl groups. The structure of these diastereomeric adducts was further probed by different hyperfine techniques (ENDOR and HYSCORE), although no structural differences were detected between these adducts using these techniques. The diastereomeric adducts were found to possess lower symmetry, as evidenced by rhombic g tensors and inequivalent Himine couplings. This was caused by the selective binding mode of MBA onto one side of the chiral CuII complex. DFT calculations were performed on the R,R-[Cu(1)] + S-MBA and R,R-[Cu(1)] + R-MBA adducts. A distinct difference in orientation and binding mode of the MBA was identified in both adducts, confirming the experimental results. The preferred heterochiral R,R-[Cu(1)] + S-MBA adduct was found to be 5 kJ mol–1 lower in energy compared to the homochiral adduct. A delicate balance of steric repulsion between the α-proton (attached to the asymmetric carbon atom) of MBA and the methine proton (attached to the asymmetric carbon atom) of [Cu(1)] was crucial in the stereoselective binding." @default.
- W2022886086 created "2016-06-24" @default.
- W2022886086 creator A5009469968 @default.
- W2022886086 creator A5047250570 @default.
- W2022886086 creator A5054144764 @default.
- W2022886086 creator A5061779083 @default.
- W2022886086 creator A5073603226 @default.
- W2022886086 creator A5087732190 @default.
- W2022886086 creator A5088399140 @default.
- W2022886086 creator A5088500220 @default.
- W2022886086 date "2011-06-27" @default.
- W2022886086 modified "2023-10-03" @default.
- W2022886086 title "Visualizing Diastereomeric Interactions of Chiral Amine–Chiral Copper Salen Adducts by EPR Spectroscopy and DFT" @default.
- W2022886086 cites W152156713 @default.
- W2022886086 cites W1543345750 @default.
- W2022886086 cites W1666767434 @default.
- W2022886086 cites W1967286963 @default.
- W2022886086 cites W1967700647 @default.
- W2022886086 cites W1969024947 @default.
- W2022886086 cites W1969885133 @default.
- W2022886086 cites W1970446591 @default.
- W2022886086 cites W1971644913 @default.
- W2022886086 cites W1973005785 @default.
- W2022886086 cites W1973724691 @default.
- W2022886086 cites W1975262546 @default.
- W2022886086 cites W1978025582 @default.
- W2022886086 cites W1980478926 @default.
- W2022886086 cites W1980481325 @default.
- W2022886086 cites W1980864184 @default.
- W2022886086 cites W1982473007 @default.
- W2022886086 cites W1988303767 @default.
- W2022886086 cites W1989123620 @default.
- W2022886086 cites W1989807773 @default.
- W2022886086 cites W1993159930 @default.
- W2022886086 cites W1995780574 @default.
- W2022886086 cites W2012866556 @default.
- W2022886086 cites W2013226985 @default.
- W2022886086 cites W2015864415 @default.
- W2022886086 cites W2016651664 @default.
- W2022886086 cites W2018957483 @default.
- W2022886086 cites W2019747502 @default.
- W2022886086 cites W2021750069 @default.
- W2022886086 cites W2023271753 @default.
- W2022886086 cites W2026395091 @default.
- W2022886086 cites W2026962909 @default.
- W2022886086 cites W2030971064 @default.
- W2022886086 cites W2031802147 @default.
- W2022886086 cites W2034571753 @default.
- W2022886086 cites W2037267833 @default.
- W2022886086 cites W2037824336 @default.
- W2022886086 cites W2043086932 @default.
- W2022886086 cites W2044425708 @default.
- W2022886086 cites W2051313688 @default.
- W2022886086 cites W2057177527 @default.
- W2022886086 cites W2060038790 @default.
- W2022886086 cites W2064216426 @default.
- W2022886086 cites W2065290596 @default.
- W2022886086 cites W2067275809 @default.
- W2022886086 cites W2070943260 @default.
- W2022886086 cites W2071253769 @default.
- W2022886086 cites W2071602727 @default.
- W2022886086 cites W2076316855 @default.
- W2022886086 cites W2076701909 @default.
- W2022886086 cites W2077292478 @default.
- W2022886086 cites W2078056126 @default.
- W2022886086 cites W2078146328 @default.
- W2022886086 cites W2078367553 @default.
- W2022886086 cites W2079093854 @default.
- W2022886086 cites W2080304919 @default.
- W2022886086 cites W2080327260 @default.
- W2022886086 cites W2083993424 @default.
- W2022886086 cites W2084699035 @default.
- W2022886086 cites W2086827956 @default.
- W2022886086 cites W2092449240 @default.
- W2022886086 cites W2094114797 @default.
- W2022886086 cites W2094249057 @default.
- W2022886086 cites W2094456436 @default.
- W2022886086 cites W2103400998 @default.
- W2022886086 cites W2110433212 @default.
- W2022886086 cites W2113581777 @default.
- W2022886086 cites W2120252901 @default.
- W2022886086 cites W2130949639 @default.
- W2022886086 cites W2131009808 @default.
- W2022886086 cites W2133530341 @default.
- W2022886086 cites W2140055288 @default.
- W2022886086 cites W2142576918 @default.
- W2022886086 cites W2146051607 @default.
- W2022886086 cites W2159344376 @default.
- W2022886086 cites W2160928947 @default.
- W2022886086 cites W2402288051 @default.
- W2022886086 cites W2500210460 @default.
- W2022886086 cites W292856407 @default.
- W2022886086 cites W3006506142 @default.
- W2022886086 cites W3138829171 @default.
- W2022886086 cites W4294555139 @default.
- W2022886086 cites W4297405635 @default.
- W2022886086 cites W4297851215 @default.
- W2022886086 doi "https://doi.org/10.1021/ic200113u" @default.