Abstract:
:The mechanism and regioselectivity of [3+2] cycloaddition (32CA) reactions of benzonitrile oxide with ethyl trans-cinnamate, ethyl crotonate and trans-2-penten-1-ol has been studied in gas phase and in acetonitrile, ethyl acetate and tetrahydrofuran using the B3LYP functional in connection with 6-31G(d) basis set. The 32CA reactions followed one-step mechanism with asynchronous TSs. The calculated global electron density transfer (GEDT) at the TSs showed electronic flux from benzonitrile oxide to ethyl trans-cinnamate and ethyl crotonate, while the electronic flux from trans-2-penten-1-ol to benzonitrile oxide was predicted, in complete agreement with the Conceptual Density Functional Theory (CDFT) indices. The regioselectivity is correctly described in coherence with the experiment data. The intermolecular interaction at the TSs was realized through visualization and quantification by means of independent gradient model (IGM) analysis based on promolecular density.
journal_name
J Mol Modeljournal_title
Journal of molecular modelingauthors
Abbiche K,Acharjee N,Salah M,Hilali M,Laknifli A,Komiha N,Marakchi Kdoi
10.1007/s00894-020-04547-6subject
Has Abstractpub_date
2020-09-22 00:00:00pages
279issue
10eissn
1610-2940issn
0948-5023pii
10.1007/s00894-020-04547-6journal_volume
26pub_type
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