Reactions of 2,3-Dibromonaphthalene-1,4-Dione and  Pyridyl Amines: X-ray Structures, DFT Investigations, and Selective Detection of the Hg2+ and Ni2+ Ions

Gunjan Aggrwal1

Sunita Salunke-Gawali1,*,Email

Shridhar P. Gejji1

ilind Nikalje1

Debamitra Chakravarty2

Prakash L. Verma1

Prajkta Gosavi-Mirkute1

Shital Harihar1

Mahesh Jadhav1 

Vedavati G. Puranik3

1Department of Chemistry, Savitribai Phule Pune University, Pune, Maharashtra State, 411007, India

2Central Instrumentation Facility, Savitribai Phule Pune University, Pune,   Maharashtra State, 411007, India

3Centre for material Characterization, National Chemical Laboratory, Pashan Road, Maharashtra State, Pune, 411008, India

Abstract

In this work, the products formed by the reaction between 2,3-dibromonaphthalene-1,4-dione with (pyridine-2-yl)methanamine and (pyridine-4-yl)methanamine are discussed in detial. The products 2-amino-3-bromonaphthalene-1,4-dione (A) and 2-aminonaphthalene-1,4-dione (B(1)) obtained are characterized through 1H and 13C-NMR, FTIR, mass spectrometry, single-crystal X-ray diffraction experiments, which are in conjunction with wB97X based density functional theory. Compound A can effectively and selectively detect Hg2+ and Ni2+ ions, and proposes a potential mechanism of action.