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Probing intramolecular B-N interactions in ortho-aminomethyl arylboronic acids

Publication ,  Journal Article
Collins, BE; Sorey, S; Hargrove, AE; Shabbir, SH; Lynch, VM; Anslyn, EV
Published in: Journal of Organic Chemistry
June 5, 2009

(Chemical Equation Presented) This work investigates the interplay between the intramolecular B-N dative bonding and solvent insertion in various ortho-methylamino arylboronic acids in protic media. 11B NMR experiments were conducted to study the effect that the degree of substitution of the amine group has on B-N bonding versus solvent insertion. It was found that there is a slight increase in the amount of B-N dative bonding on going from a tertiary to a secondary to a primary amine group, but that solvent insertion dominates in all cases of the boronate esters. A X-ray crystal structure gives further insight into the structure of the solventinserted boronate esters, showing that the inserted solvent has its hydrogen primarily on the amine. Lastly, studies of the use of boronate esters as receptors for simple alcohols and carboxylic acids are described. © 2009 American Chemical Society.

Duke Scholars

Published In

Journal of Organic Chemistry

DOI

ISSN

0022-3263

Publication Date

June 5, 2009

Volume

74

Issue

11

Start / End Page

4055 / 4060

Related Subject Headings

  • Organic Chemistry
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry
 

Citation

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Collins, B. E., Sorey, S., Hargrove, A. E., Shabbir, S. H., Lynch, V. M., & Anslyn, E. V. (2009). Probing intramolecular B-N interactions in ortho-aminomethyl arylboronic acids. Journal of Organic Chemistry, 74(11), 4055–4060. https://doi.org/10.1021/jo900187a
Collins, B. E., S. Sorey, A. E. Hargrove, S. H. Shabbir, V. M. Lynch, and E. V. Anslyn. “Probing intramolecular B-N interactions in ortho-aminomethyl arylboronic acids.” Journal of Organic Chemistry 74, no. 11 (June 5, 2009): 4055–60. https://doi.org/10.1021/jo900187a.
Collins BE, Sorey S, Hargrove AE, Shabbir SH, Lynch VM, Anslyn EV. Probing intramolecular B-N interactions in ortho-aminomethyl arylboronic acids. Journal of Organic Chemistry. 2009 Jun 5;74(11):4055–60.
Collins, B. E., et al. “Probing intramolecular B-N interactions in ortho-aminomethyl arylboronic acids.” Journal of Organic Chemistry, vol. 74, no. 11, June 2009, pp. 4055–60. Scopus, doi:10.1021/jo900187a.
Collins BE, Sorey S, Hargrove AE, Shabbir SH, Lynch VM, Anslyn EV. Probing intramolecular B-N interactions in ortho-aminomethyl arylboronic acids. Journal of Organic Chemistry. 2009 Jun 5;74(11):4055–4060.
Journal cover image

Published In

Journal of Organic Chemistry

DOI

ISSN

0022-3263

Publication Date

June 5, 2009

Volume

74

Issue

11

Start / End Page

4055 / 4060

Related Subject Headings

  • Organic Chemistry
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry