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- W2806688304 abstract "Bonding is a fundamental aspect of organic chemistry, yet the magnitude of C=C bonding in [n]cumulenes as a function of increasing chain length has yet to be experimentally verified for derivatives longer than n=5. The synthesis of a series of apolar and unsymmetrically substituted tetraaryl[n]cumulenes (n=3, 5, 7, 9) was developed and rotational barriers for Z/E isomerization were measured using dynamic VTNMR spectroscopy. Both experiment and theory confirm a dramatic reduction in the rotational barrier (through estimation of ΔG≠rot for the isomerization) across the series, from >24 to 19 to 15 to 11 kcal-1 in [n]cumulenes with n=3, 5, 7, 9, respectively. The reduction in cumulenic bonding in longer cumulenes thus affords bond rotational barriers that are more characteristic of a sterically hindered single bond than that of a double bond." @default.
- W2806688304 created "2018-06-13" @default.
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- W2806688304 date "2018-07-02" @default.
- W2806688304 modified "2023-09-29" @default.
- W2806688304 title "Double Bonds? Studies on the Barrier to Rotation about the Cumulenic C=C Bonds of Tetraaryl[ <i>n</i> ]cumulenes ( <i>n=</i> 3, 5, 7, 9)" @default.
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- W2806688304 doi "https://doi.org/10.1002/anie.201802137" @default.
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