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• W4382243359 abstract "This paper documents and reinvestigates the solid-state and crystal structures of 4,4′-azobis-4-cyanopentanoic acid (ACPA), a water-soluble azobis-nitrile of immense utility as a radical initiator in living polymerizations and a labile mechanophore that can be embedded within long polymer chains to undergo selective scission under mechanical activation. Surprisingly, for such applications, both the commercially available reagent and their derivatives are used as “single initiators” when this azonitrile is actually a mixture of stereoisomers. Although the racemate and meso compounds were identified more than half a century ago and their enantiomers were separated by classical resolution, there have been confusing narratives dealing with their characterization, the existence of a conglomeratic phase, and fractional crystallization. Our results report on the X-ray crystal structures of all stereoisomers for the first time, along with further details on enantiodiscrimination and the always intriguing arguments accounting for the stability of homochiral versus heterochiral crystal aggregates. To this end, metadynamic (MTD) simulations on stereoisomer molecular aggregates were performed to capture the incipient nucleation events at the picosecond time scale. This analysis sheds light on the driving homochiral aggregation of ACPA enantiomers." @default.
• W4382243359 created "2023-06-28" @default.
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• W4382243359 date "2023-06-27" @default.
• W4382243359 modified "2023-10-14" @default.
• W4382243359 title "Revisiting Homochiral <i>versus</i> Heterochiral Interactions through a Long Detective Story of a Useful Azobis-Nitrile and Puzzling Racemate" @default.
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• W4382243359 doi "https://doi.org/10.1021/acs.cgd.3c00372" @default.
• W4382243359 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/37547876" @default.
• W4382243359 hasPublicationYear "2023" @default.
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