Mechanochemical Mediated Coexistence of B←N Coordination and Hydrogen Bonding

María Guadalupe Vasquez-Ríos; Gonzalo Campillo-Alvarado; Leonard MacGillivray

doi:10.1002/anie.202308350

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Mechanochemical Mediated Coexistence of B←N Coordination and Hydrogen Bonding

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Mechanochemical Mediated Coexistence of B←N Coordination and Hydrogen Bonding

María Guadalupe Vasquez-Ríos, Gonzalo Campillo-Alvarado and Leonard MacGillivray

Angewandte Chemie (International ed.), Vol.62(35), e202308350

08/28/2023

DOI: 10.1002/anie.202308350

PMID: 37365138

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Abstract

Mechanochemistry afforded a photoactive cocrystal via coexisting (B)O-H⋅⋅⋅N hydrogen bonds and B←N coordination. Specifically, solvent-free mechanochemical ball mill grinding and liquid-assisted grinding of a boronic acid and an alkene resulted in mixtures of hydrogen-bonded and coordinated complexes akin to mixtures of noncovalent complexes that can be obtained in solution in equilibria processes. The alkenes of the hydrogen-bonded assembly undergo an intermolecular [2+2] photodimerization in quantitative conversion, effectively reporting the outcome of the self-assembly processes. Our results suggest that interplay involving noncovalent bonds subjected to mechanochemical conditions can lead to functional solids where, in the current case, the weaker hydrogen-bonded structure predominates.

mechanochemical

reporter

cocrystal

photoactive

B-coordination

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Details

Title: Subtitle: Mechanochemical Mediated Coexistence of B←N Coordination and Hydrogen Bonding
Creators: María Guadalupe Vasquez-Ríos - University of Iowa
Gonzalo Campillo-Alvarado - Reed College
Leonard MacGillivray - University of Iowa, Chemistry
Resource Type: Journal article
Publication Details: Angewandte Chemie (International ed.), Vol.62(35), e202308350
DOI: 10.1002/anie.202308350
PMID: 37365138
NLM abbreviation: Angew Chem Int Ed Engl
ISSN: 1433-7851
eISSN: 1521-3773
Publisher: Wiley
Grant note: National Science Foundation (GrantNumber(s): DMR-2221086) National Science Foundation (GrantNumber(s): DMR-1708673) National Science Foundation (GrantNumber(s): CHE-1828117) Consejo Nacional de Ciencia y Tecnología M.J. Murdock Charitable Trust (GrantNumber(s): NS-202222588)
Language: English
Electronic publication date: 06/26/2023
Date published: 08/28/2023
Academic Unit: Pharmaceutical Sciences and Experimental Therapeutics; Chemistry
Record Identifier: 9984443359602771

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