Ontology highlight
ABSTRACT:
SUBMITTER: Narsaria AK
PROVIDER: S-EPMC6771859 | biostudies-literature | 2019 Jul
REPOSITORIES: biostudies-literature
Chemistry (Weinheim an der Bergstrasse, Germany) 20190708 42
The unusually fast Diels-Alder reactions of [5]cyclophanes were analyzed by DFT at the BLYP-D3(BJ)/TZ2P level of theory. The computations were guided by an integrated activation-strain and Kohn-Sham molecular orbital analysis. It is revealed why both [5]metacyclophane and [5]paracyclophane exhibit a significant rate enhancement compared to their planar benzene analogue. The activation strain analyses revealed that the enhanced reactivity originates from 1) predistortion of the aromatic core resu ...[more]