Conformational Analysis of Bis-triazole Derivatives Using Computational Studies in Understanding Aryl C-H--- Anion Interaction

Abstract

Recently, Beckendorf et al. reported that in a N-arylation reaction, bis-triazole acted as better acceptor than thiourea. In this reaction the interaction of counter anion with hydrogens of acceptors is stronger in the case of bis-triazole than thiourea . There are various factors that make it better acceptor because of it’s stability, synthetic accessibility, selectivity and chemical compatibility. But, this article did not discuss about the conformational structure of bis-triazole. Conformational preferences have been studied for bis-triazole molecule in order to understand the minimum energy conformers. After analyzing the PES with biaryl rotational bonds, we obtained two minimum energy structures that were optimized at DFT level of theory. The interaction of bis-triazole with Cl and Br has also been studied for the minimum energy structure at HF/STO-3G level. However, only for the coplanar conformer, we could optimize the geometry. The other structures failed to optimize.Further studies at higher level of theory are needed for detailed understanding of the anion and C-H interactions.