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Is It Possible to Achieve Organic Superbases beyond the Basicity Limit Using Tetrahedrane Scaffolds?
Author(s) -
Valadbeigi Younes,
Vianello Robert
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202001407
Subject(s) - protonation , deprotonation , chemistry , affinities , ring (chemistry) , proton , limit (mathematics) , organic base , proton affinity , medicinal chemistry , computational chemistry , stereochemistry , organic chemistry , ion , mathematical analysis , physics , mathematics , quantum mechanics
Abstract Substituted tetrahedranes offer exceptional carbon bases with the gas‐phase proton affinities (PAs) up to 356 kcal mol −1 , due to the strain‐induced ring opening upon protonation. Additional tetrahedrane moieties exert a dramatic basicity amplification to PAs reaching 600 kcal mol −1 , being the strongest organic superbases reported, clearly surpassing the proposed limit of achievable basicities (Angew. Chem. Int. Ed. 2015, 54, 9262). However, because protonation/deprotonation of these compounds is not reversible, PAs of the opened‐cage isomers were calculated which were lower than the basiciy limit.