Highly stable naphthalene core based novel cleft-shaped strain molecule: influence of intermolecular H-bonding architectures. Issue 64 (21st June 2016)

• Record Type: Journal Article
• Authors: Panja, Sumit Kumar; Dwivedi, Nidhi; Saha, Satyen
• Is Part Of: RSC advances. Volume 6:Issue 64(2016)
• Page Start: 59574
• Page End: 59581
• Publication Date: 2016-06-21
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c6ra06855c
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : High thermal stability of a 8 membered naphthalene core based fused nitrogen bridged 1, 5-dioxocin is found to be due to the coexistence of several weak interactions. Catalytic property of this molecule for a condensation reaction is also explored. Abstract : The significance of intermolecular classical and non-classical H-bonding interactions in the stabilization of a naphthalene core based conformationally rigid cleft-shaped 1, 5-dioxocin (BNAP) is presented here. The importance of H-bonding interactions to account for the unusual stability of a catalytically important novel molecule is reported for the first time. In addition to strong CH⋯π interactions, the formation of the unique intermolecular seven-membered H-bonded ring in the crystalline state through classical and non-classical H-bonding interaction was found to provide the unusual stability. This supramolecular structure was also found to impart stability in the presence of a strong acid as evident from the detailed UV-Visible spectroscopic studies. In addition to DFT calculations, the Hirshfeld surfaces, mapped with d norm, and 2D fingerprint plots, support the existence of these classical and non-classical H-bonding and CH⋯π interactions. Furthermore, BNAP shows its remarkable catalytic activity for the Knoevenagel condensation reaction.