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2006 | 4 | 4 | 646-665

Article title

Hybrid density functional theory investigation of a series of alloxan-based thiosemicarbazones and semicarbazones


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Recently, the synthesis and the NMR characterization of a series of eight alloxan-based thiosemicarbazones and semicarbazones were reported. These compounds exhibit a strongly hydrogenbonded hydrazinic proton that is a part of a characteristic six-membered ring. This proton is highly deshielded and resonates far downfield in the proton NMR spectra. In this report, mPW1PW91/6-31+G(d,p) calculations have been used to investigate the structure and other molecular properties of this series of eight compounds. The relationship between the 1H and 13C NMR chemical shifts and various geometric parameters was investigated, and linear relationships for proton peaks that are involved in hydrogen-bond interactions were found.










Physical description


1 - 12 - 2006
1 - 12 - 2006


  • Department of Chemistry, Tennessee Technological University, Cookeville, Tennessee, 38505, USA
  • Department of Chemistry, Tennessee Technological University, Cookeville, Tennessee, 38505, USA
  • Department of Chemistry, Tennessee Technological University, Cookeville, Tennessee, 38505, USA


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  • [37] IUPAC names: ALL-TSC = pyrimidine-2,4,5,6(1H,3H)-tetrone 5-thiosemicarbazone, ALL-MTSC = pyrimidine-2,4,5,6(1H,3H)-tetrone 5-(N-methylthiosemicarbazone), ALL-ETSC = pyrimidine-2,4,5,6(1H,3H)-tetrone 5-(N-ethylthiosemicarbazone), ALL-BzTSC = pyrimidine-2,4,5,6(1H,3H)-tetrone 5-(N-benzylthiosemicarbazone), ALL-PTSC = pyrimidine-2,4,5,6(1H,3H)-tetrone 5-(N-phenylthiosemicarbazone), ALL-DMTSC = pyrimidine-2,4,5,6(1H,3H)-tetrone 5-(N,N-dimethylthiosemicarbazone), ALL-SC = pyrimidine-2,4,5,6(1H,3H)-tetrone 5-semicarbazone, and ALL-PSC = pyrimidine-2,4,5,6(1H,3H)-tetrone 5-(N-phenylsemicarbazone).
  • [38] The Supplementary Information includes geometries in Cartesian coordinates, calculated isotropic magnetic shielding tensors, energies, and frequencies for all stationary points optimized in this work and the Mulliken atomic charges for the minimum structures. This material is available upon request from the corresponding author. E-mail your inquiries to albu@tntech.edu.
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