A newly synthesized nitrogen-rich derivative of bicyclic quinoxaline-Structural and conceptual DFT reactivity study

被引：22

作者：

Abad, Nadeem ^{[1
]}

Hajji, Melek ^{[2
]}

Ramli, Youssef ^{[3
]}

Belkhiria, Marwa ^{[4
]}

Elmgirhi, Salima Moftah H. ^{[5
]}

Habib, Mohamed A. ^{[5
]}

Guerfel, Taha ^{[2
]}

Mague, Joel T. ^{[6
]}

Essassi, El Mokhtar ^{[1
]}

机构：

[1] Univ Mohammed 5, Lab Chim Organ Heterocycl, Ctr Rech Sci Medicaments, URAC 21,Pole Competence Pharmacochim,Fac Sci, Av Ibn Battouta,Bp 1014, Rabat, Morocco

[2] Univ Kairouan, Res Unit Electrochem Mat & Environm, Kairouan 3100, Tunisia

[3] Mohammed V Univ, Fac Med & Pharm, Lab Med Chem, Rabat, Morocco

[4] Fac Sci Monastir, Lab Chim Heterocycl Prod Nat & Reactivite LCHPNR, Monastir, Tunisia

[5] Sirte Univ, Fac Educ, Dept Chem, Sirte, Libya

[6] Tulane Univ, Dept Chem, New Orleans, LA 70118 USA

来源：

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY | 2020年 / 33卷 / 06期

关键词：

DFT; chemical reactivity theory; Hirshfeld surfaces; NCI topological analysis; quinoxaline derivatives; weak noncovalent interactions; DENSITY-FUNCTIONAL THEORY; DOPAMINERGIC-NEURONS; INDEX;

D O I：

10.1002/poc.4055

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel nitrogen-rich compound featured bicyclic quinoxaline as a basic core structure has been synthesized, 1-{[1-(3-azido-2-hydroxypropyl)-1H-1,2,3-triazol-4-yl]methyl}-3-methyl-1,2-dihydroquinoxalin-2-one with formula C15H16N8O2, 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.

引用

页数：9

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