Intramolecular hydrogen bonds in the sulfonamide derivatives of oxamide, dithiooxamide, and biuret. FT-IR and DFT study, AIM and NBO analysis

The hydrogen bonding in [(1-arylsulfonylamino-2,2,2-trichloro)ethyl]biuret 1, [(1-arylsulfonylamino-2,2,2-trichloro)ethyl]oxamide 2, and [(1-arylsulfonylamino-2,2,2-trichloro)ethyl]dithiooxamide 3, the sulfonamide derivatives of biuret 4, oxamide 5, and dithiooxamide 6, has been studied by molecular spectroscopy and DFT theoretical calculations including frequency calculations, at the B3LYP/6-311+G (d,p) level of theory. The analysis of the C=O center dot center dot center dot HN and C=S center dot center dot center dot HN intramolecular hydrogen bonds closing the five- and six-membered rings employing the atoms-in-molecules (AIM) method using the MP2(full)/6-311++G(d,p) wave functions has shown that their stability is increased in comparison to the original molecules and is much higher in the thiocarbonyl compounds. The results of the AIM and the NBO analysis of donor acceptor interactions are in good agreement with each other and with the experimental FT-IR spectroscopy data. (C) 2010 Elsevier Ltd. All rights reserved.