Abstract
In this manuscript, we combined ab initio calculations (RI-MP2/def2-TZVPD level of theory) and a search in the CSD (Cambridge Structural Database) to analyze the influence of aromatic substitution in charge-assisted multivalent halogen bonding complexes. We used a series of benzene substituted iodine derivatives C6H4(IF4)Y (Y = H, NH2, OCH3, F, CN, and CF3) as Lewis acids and used Cl− as electron rich interacting atoms. We have represented the Hammett’s plot and observed a good regression coefficient (interaction energies vs. Hammett’s σ parameter). Additionally, we demonstrated the direct correlation between the Hammett’s σ parameter and the value of molecular electrostatic potential measured at the I atom on the extension of the C–I bond. Furthermore, we have carried out AIM (atoms in molecules) and NBO (natural bonding orbital) analyses to further describe and characterize the interactions described herein. Finally, we have carried out a search in the CSD (Cambridge Structural Database) and found several X-ray structures where these interactions are present, thus giving reliability to the results derived from the calculations.
Funder
Ministerio de Economía y Competitividad
Subject
Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science
Reference55 articles.
1. Binding Mechanisms in Supramolecular Complexes
2. Principles and Methods in Supramolecular Chemistry;Schneider,2000
3. Supramolecular Chemistry Concepts and Perspectives;Lehn,1995
4. Supramolecular Chemistry: An Introduction;Vögtle,1993
5. Supramolecular Chemistry;Beer,1999
Cited by
9 articles.
订阅此论文施引文献
订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献