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A newly synthesized nitrogen‐rich derivative of bicyclic quinoxaline—Structural and conceptual DFT reactivity study
Author(s) -
Abad Nadeem,
Hajji Melek,
Ramli Youssef,
Belkhiria Marwa,
Moftah H. Elmgirhi Salima,
A. Habib Mohamed,
Guerfel Taha,
T. Mague Joel,
Essassi El Mokhtar
Publication year - 2020
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.4055
Subject(s) - quinoxaline , chemistry , reactivity (psychology) , bicyclic molecule , supramolecular chemistry , nucleophile , electrophile , non covalent interactions , derivative (finance) , density functional theory , computational chemistry , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , crystal structure , molecule , hydrogen bond , catalysis , medicine , alternative medicine , pathology , financial economics , economics
Abstract Novel nitrogen‐rich compound featured bicyclic quinoxaline as a basic core structure has been synthesized, 1‐{[1‐(3‐azido‐2‐hydroxypropyl)‐1 H ‐1,2,3‐triazol‐4‐yl]methyl}‐3‐methyl‐1,2‐dihydroquinoxalin‐2‐one with formula C 15 H 16 N 8 O 2 , and their structural and chemical reactivity aspects have been comprehensively discussed. Nature, role, and relative contribution of weak noncovalent interactions in supramolecular assembly have been assessed through single‐crystal analysis and computational approaches. Useful information about the global and local reactivity were obtained from Conceptual Density Functional Theory at wB97X‐D/cc‐pVDZ level. Studied system could act as strong electrophile and/or moderate nucleophile in polar organic reactions. We hope this study will provide deeper insight in the knowledge of the synthesis and chemistry of the quinoxaline and quinoxaline derivatives.