Theoretical Study on the Aza-Diels-Alder Reaction Catalyzed by PHCl2 Lewis Acid via Pnicogen Bonding

The Journal of Physical Chemistry. a
Fereshteh Yaghoobi, Mahdi Sohrabi Mahboub

Abstract

The reaction mechanism of the Aza-Diels-Alder (A-D-A) cycloaddition reaction between X2C═NNH2, where X = H, F, Cl, Br, and 1,3-butadiene catalyzed by a PHCl2Lewis acid was characterized using density functional theory calculations. The influences of various substituents of X on the studied reaction were analyzed using the activation strain model (ASM), which is also termed as the distortion-interaction model. Calculations showed that the smallest and largest values of the activation energies belong to the substituents of F and Br, respectively. The activation energy of the studied reactions was decreased within 8.6 kcal·mol-1in the presence of PHCl2catalyst. Investigations showed that the pnicogen bonding is adequately capable of activating the A-D-A reaction. The quantum theory of atoms in molecules (QTAIM) and natural bond orbital (NBO) analysis were implemented to understand the nature of C4,Cbut···CXImand C1,Cbut···NXImbonds at the TS structures. Additionally, the energy decomposition analysis (EDA) based on the ETS-NOCV scheme was used to characterize the nature of C4,Cbut···CXImand C1,Cbut···NXImbond. The results of the study mirror the fact that the PHCl2Lewis acid may be suggested as a simple suitable catalyst for exper...Continue Reading

References

May 18, 2000·The Journal of Organic Chemistry·S Yamabe, T Minato
Jan 6, 2005·Organic & Biomolecular Chemistry·Václav Jurcik, René Wilhelm
Aug 10, 2007·Journal of the American Chemical Society·Daniel H Ess, K N Houk
Mar 10, 2011·The Journal of Chemical Physics·Steve Scheiner
Apr 20, 2011·Chemistry : a European Journal·Stefan ZahnBarbara Kirchner
Nov 9, 2012·Accounts of Chemical Research·Steve Scheiner
May 8, 2013·Angewandte Chemie·Florian KniepStefan M Huber
Nov 20, 2013·The Journal of Physical Chemistry. a·K Eskandari, N Mahmoodabadi
Mar 5, 2014·The Journal of Physical Chemistry. a·Liangyu Guan, Yirong Mo
May 7, 2014·Chemical Communications : Chem Comm·Stefan H JungbauerStefan M Huber
Oct 18, 2014·The Journal of Physical Chemistry. a·Dani SetiawanDieter Cremer
Dec 11, 2014·Physical Chemistry Chemical Physics : PCCP·Sounak SarkarT N Guru Row
Feb 26, 2016·The Journal of Organic Chemistry·Vincent de Paul N Nziko, Steve Scheiner
Feb 6, 2017·The Journal of Physical Chemistry. a·Janet E Del BeneGoar Sánchez-Sanz

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Citations

Mar 30, 2021·Chemistry : a European Journal·Pascal VermeerenTrevor A Hamlin

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