Crystal and Molecular Structure Analysis in Knoevenagel Condensation Product of Substituted Napthofuran-2-Carbaldehydes

Avantika Hasija,Vasu Vasu,M Shet Prakash,V Prakash,Deepak Chopra,G Krishnasamy

doi:10.4236/csta.2020.93005

Abstract

In the current study, two novel Knoevenagel condensation products of substituted napthofuran-2-carbaldehydes were designed, synthesized and characterized. In order to study the intermolecular interactions of title compounds, single crystals were grown by slow evaporation solution growth technique at room temperature and crystal structure has been determined by single crystal X-ray diffraction technique. Both the molecules crystallize in the monoclinic centrosymmetric space group P21/c with one molecule in the asymmetric unit. In compound [4] the molecules are connected via bifurcated C-H···O=C and C-H···N=C H-bonds and van der Waals interactions forming a layered structure, whereas in compound [5a] the molecular conformation is stabilized via intramolecular C-H···O H-bond and molecule interacts with other molecule generated via 21-screw via bifurcated C-H···O=C along with C-H···N=C H-bonds, which are interacting with nitro- of other molecule generated via same symmetry operation, forming bifurcated C-H···O-N H-bonds, which helps in formation of molecular sheet-like structure.Further, in order to understand the various types and nature of intermolecular interactions in the supramolecular structure Hirshfeld surface analysis and fingerprint plot analysis was carried out.

Highlights

Furan motif posses various pharmacological and biological activities such as antituberculosis [1], anti-inflammatory [2] and antibacterial [3] activities have attracted the attention of synthetic chemists
In order to study the intermolecular interactions of title compounds, single crystals were grown by slow evaporation solution growth technique at room temperature and crystal structure has been determined by single crystal X-ray diffraction technique
Both the molecules crystallize in the monoclinic centrosymmetric space group P21/c with one molecule in the asymmetric unit

Summary

Introduction

Furan motif posses various pharmacological and biological activities such as antituberculosis [1], anti-inflammatory [2] and antibacterial [3] activities have attracted the attention of synthetic chemists. Substituted benzofurans and naptho-furans find their applications in different fields such as fluorescent sensors [4], antioxidants [5], brightening agents, and a variety of drugs and agriculture [6]. Prashanth K. et al, reported the docking analysis of naphtho-furan and benzofuran derivatives and concluded that in most of the interactions involving the nitro group formed hydrogen bond with Asp of NarL protein and might act as a potential antitubercular lead molecule [7]. The crystallization phenomenon is very important in the pharmaceutical industry because it directly affects the bioavailability of drugs [8]. The Knoevenagel condensation reaction is one of the most important reactions in which C=C bond is formed via condensation reactions of active methylene group with aldehydes or ketones that do not contain α-hydrogen [14]

Methods

Results

Conclusion