Back to Search Start Over

Role of non-conventional hydrogen bonding in controlling regioselectivity for nucleophilic aromatic substitution of 4,6-dinitroisoindoline-1,3-dione with 1,2,3-triazole isomers: a computational studies.

Authors :
Singh, Amrit
Singh, Amritpal
Amanjot
Singh, Kulvinder
Singh, Gurjaspreet
Saroa, Amandeep
Source :
Structural Chemistry. Jun2021, Vol. 32 Issue 3, p1269-1278. 10p.
Publication Year :
2021

Abstract

The nucleophilic aromatic substitution reactions of 4,6-dinitroisoindoline-1,3-dione with 1,2,3-triazole isomers, i.e., 1H-1,2,3-triazole and 2H-1,2,3-triazole, have been investigated theoretically using DFT/B3LYP calculations employing 6-31G(d,p) basis set in gas phase as well as in solvent phase. The computational studies have supported the formation of transition states via one-step concerted mechanism for the nucleophilic aromatic displacement of nitro groups with 1,2,3-triazoles rather than intermediate formation via two-step addition-elimination mechanism. The amination of 4,6-dinitroisoindoline-1,3-dione with 1,2,3-triazole isomers have revealed regioselectivity of peri-attack despite sterically favorable para-attack. The regioselectivity is attributed to the stabilization of the transition state through intra-molecular hydrogen bond C-H···O=C. This work presents the role of C-H bond as an effective hydrogen bond donor. The molecular interactions through hydrogen bonding have been investigated using AIM method. This work shall result in the synthesis of new regioselective 1,2,3-triazole-derived phthalimide compounds possessing potential biological candidature. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
10400400
Volume :
32
Issue :
3
Database :
Academic Search Index
Journal :
Structural Chemistry
Publication Type :
Academic Journal
Accession number :
149960595
Full Text :
https://doi.org/10.1007/s11224-020-01689-4