Aromaticity indices, electronic structural properties, and fuzzy atomic space investigations of naphthalene and its aza-derivatives

Moses M Edim,Obieze C Enudi,Bassey B Asuquo,Hitler Louis,Emmanuel A Bisong,John A Agwupuye,Apebende G Chioma,Joseph O Odey,Innocent Joseph,Francisca I Bassey

doi:10.1016/j.heliyon.2021.e06138

Abstract

The aromaticity and CDFT properties of naphthalene and its aza-derivatives were theoretically investigated using density functional theory (DFT) electronic structure method. The reactivity and chemistry of Azanaphthalene (1-AN), 1, 2-diazanaphthalene (1, 2-DAN), 1, 3-diazanaphthalene (1, 3-DAN), 1, 4-diazanaphthalene (1,4-DAN), 1, 5-diazanaphthalene (1, 5-DAN), 1, 6-diazanaphthalene (1, 6-DAN), 1, 7-diazanaphthalene (1,7-DAN) and 1, 8-diazanaphthalene (1, 8-DAN) were thoroughly explored and predicted focusing more on the fuzzy atomic space analysis, quantum chemical descriptors (CDFT), natural bond orbital (NBO), and structural electronic properties. The CDFT is focused on predicting the condensed Fukui function and dual descriptors along with condensed local electrophilicity and nucleophilicity investigation. From the aromaticity computational study, 1,7-DAN gave PDI, FLU, FLU-π, PLR, HOMA, BIRD and LOLIPOP values of approximately one (1) was found to be the most aromatic in the group, and strongest π-stacking ability. The aromaticity follows the trend: 1, 7-DAN > 1, 8-DAN > 1, 5-DAN > 1, 6-DAN > 1, 4-DAN > 1, 2-DAN > 1-AN > naphthalene. The second order perturbation energy NBO analysis revealed that the 3 highest stabilization energies in the molecules are C6–Na to C3–C4(π∗−π∗ 236.90 kcal/mol) of 1, 6-DAN, C3–C4 to C1–C2 (π∗−π∗236.37 kcal/mol) of 1-AN and C7–N10 to C2–C4 (π∗−π∗235 kcal/mol) of 1, 3-DAN.

Highlights

We encounter aromatics in our daily lives
This study investigates the effect of fused nitrogen atoms in the stability, aromaticity and reactivity indices of naphthalene, the reactive sites and their nature is determined using Conceptual density functional theory (CDFT) parameters
The interest is the magnitude and trends in property values as we move from Naphthalene to the mono-substituted azanaphthalene, and as amongst the diazanaphthalenes (1, 2-DAN, 1, 3-DAN, 1, 4-DAN, 1, 5DAN, 1, 6-DAN, 1, 7-DAN AND 1, 8-DAN)

Summary

Introduction

We encounter aromatics in our daily lives. The chemistry of our body would be distorted in the absence of aromatic molecules in our system, we would be lacking many materials needs. About 35 million tons of aromatic compounds are manufactured in the world every year to produce essential chemicals and polymers, such as polyester, nylon, vinyl polymers (e.g. styrene) etc They play essential biochemical roles in living systems [1, 2]. Diazanaphthalenes are a broad class of N-heteroaromatic compounds with several technological and biological applications They consist of a naphthalene double ring in which two of the carbon atoms have been replaced with Nitrogen atom. 1,8-naphthyridine derivatives have Medicinal properties such as anti-HIV, anti-cancer, anti-inflammatory, anti-malarial, anti-bacterial, anti-protozoans, anti-mycobacterial and anti-platelet [7] Some of their applications of are attributed to their ability to form association dimers through non-covalent interactions [8, 9, 10]

Objectives

Results

Conclusion