Experimental validation of bifurcated hydrogen bond of 2,5-lutidinium bromanilate and its charge density distribution

Niranjana Devi Rajendran,Natarajan Mookan,Israel Samuel,Sarath Babu Mookan

doi:10.1007/s11696-020-01107-3

Abstract

2,5-Lutidinium bromanilate is a molecular complex that consists of bromanilic acid and 2,5-lutidine in which hydrogen-bonding interactions occur between them, producing a charge-assisted bifurcated N–H…O hydrogen bond. Bond characteristics are determined from the experimental charge density distribution of the molecular complex using the Hansen–Coppens model. The electron density, topological properties, electrostatic potential and atomic charges of the molecule have been investigated to better understand the atomic, molecular and electronic properties in a detailed manner. The electronic nature of the significantly important charge-assisted bifurcated hydrogen bond has been analyzed with the help of topological properties.Graphic abstract

Highlights

In recent years, the occurrence of molecular complexes in molecular crystals has received considerable attention, especially from the viewpoint of drug design and crystal engineering
In such a molecular complex that consists of bromanilic acid with the N-heterocyclic compound 2,5-lutidine, intra- and/or intermolecular interaction occurs between the bromanilic acid molecule and the N heteroatom of the pyridine ring of 2,5-lutidine, producing a charge-assisted bifurcated N–H...O hydrogen bond
For obtaining information about the geometric arrangement of the atoms in the unit cell, the molecular structure of 2,5-LB has been discussed with the help of bond length, bond angle and dihedral angle

Summary

Introduction

The occurrence of molecular complexes in molecular crystals has received considerable attention, especially from the viewpoint of drug design and crystal engineering. The significant behavior of hydrogen-bonding interactions plays a key role in the effective production of ionic molecular complexes (Thomas et al 2013), in the design of pharmaceutical materials. In such a molecular complex that consists of bromanilic acid with the N-heterocyclic compound 2,5-lutidine, intra- and/or intermolecular interaction occurs between the bromanilic acid molecule and the N heteroatom of the pyridine ring of 2,5-lutidine, producing a charge-assisted bifurcated N–H...O hydrogen bond. The charge-assisted hydrogen bond helps in the salt formation process with desired properties in drug engineering

Methods

Results

Conclusion