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Issue 47, 2014
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Why do the [PhSiO1.5]8,10,12 cages self-brominate primarily in the ortho position? Modeling reveals a strong cage influence on the mechanism

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Abstract

(PhSiO1.5)8,10,12 cages are bulky, electron withdrawing like CF3; yet self-brominate (60 °C), favoring ortho substitution: PhT8 (≈85%), PhT10 (≈75%) and PhT12 (60%). First-principles calculations suggest bromination initiates when Br2 is “trapped” via H-bonding to ortho-H's, followed by polarization via strong interactions with cage faces, possibly cage LUMOs.

Graphical abstract: Why do the [PhSiO1.5]8,10,12 cages self-brominate primarily in the ortho position? Modeling reveals a strong cage influence on the mechanism

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Article information


Submitted
05 Sep 2014
Accepted
20 Oct 2014
First published
20 Oct 2014

Phys. Chem. Chem. Phys., 2014,16, 25760-25764
Article type
Communication
Author version available

Why do the [PhSiO1.5]8,10,12 cages self-brominate primarily in the ortho position? Modeling reveals a strong cage influence on the mechanism

M. Bahrami, H. Hashemi, X. Ma, J. Kieffer and R. M. Laine, Phys. Chem. Chem. Phys., 2014, 16, 25760
DOI: 10.1039/C4CP03997A

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