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- W2238385475 endingPage "980" @default.
- W2238385475 startingPage "969" @default.
- W2238385475 abstract "The solution phase self-assembly of boronate esters, diazaboroles, oxathiaboroles, and dithiaboroles from the condensation of arylboronic acids with aromatic diol, diamine, hydroxythiol, and dithiol compounds in chloroform has been investigated by 1H NMR spectroscopy and computational methods. Six arylboronic acids were included in the investigations with each boronic acid varying in the substituent at its 4-position. Both computational and experimental results show that the para-substituent of the arylboronic acid does not significantly influence the favorability of forming a condensation product with a given organic donor. The type of donor, however, greatly influences the favorability of self-assembly. 1H NMR spectroscopy indicates that condensation reactions between arylboronic acids and catechol to give boronate esters are the most favored thermodynamically, followed by diazaborole formation. Computational investigations support this conclusion. Neither oxathiaboroles nor dithiaboroles form spontaneously at equilibrium in chloroform at room temperature. Computational results suggest that the effect of borylation on the frontier orbitals of each donor helps to explain differences in the favorability of their condensation reactions with arylboronic acids. The results can inform the use of boronic acids as they are increasingly utilized in the dynamic self-assembly of organic materials and as components in dynamic combinatorial libraries." @default.
- W2238385475 created "2016-06-24" @default.
- W2238385475 creator A5021150229 @default.
- W2238385475 creator A5047206528 @default.
- W2238385475 date "2016-01-15" @default.
- W2238385475 modified "2023-09-27" @default.
- W2238385475 title "Spectroscopic and Computational Investigations of The Thermodynamics of Boronate Ester and Diazaborole Self-Assembly" @default.
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