TY - JOUR
T1 - Stability of alkyl carbocations
AU - Hansen, Thomas
AU - Vermeeren, Pascal
AU - Bickelhaupt, F. Matthias
AU - Hamlin, Trevor A.
PY - 2022/11/7
Y1 - 2022/11/7
N2 - The traditional and widespread rationale behind the stability trend of alkyl-substituted carbocations is incomplete. Through state-of-the-art quantum chemical analyses, we quantitatively established a generally overlooked driving force behind the stability of carbocations, namely, that the parent substrates are substantially destabilized by the introduction of substituents, often playing a dominant role in solution. This stems from the repulsion between the substituents and the C-X bond.
AB - The traditional and widespread rationale behind the stability trend of alkyl-substituted carbocations is incomplete. Through state-of-the-art quantum chemical analyses, we quantitatively established a generally overlooked driving force behind the stability of carbocations, namely, that the parent substrates are substantially destabilized by the introduction of substituents, often playing a dominant role in solution. This stems from the repulsion between the substituents and the C-X bond.
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U2 - 10.1039/d2cc04034d
DO - 10.1039/d2cc04034d
M3 - Article
C2 - 36254748
AN - SCOPUS:85140856258
SN - 1359-7345
VL - 58
SP - 12050
EP - 12053
JO - Chemical communications (Cambridge, England)
JF - Chemical communications (Cambridge, England)
IS - 86
ER -