Bulletin of the Korean Chemical Society

  • 제19권1호
  • /
  • Pages.110-114
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  • 1998
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Basicity of Urea: Near-Infrared Spectroscopic and Theoretical Studies on the Hydrogen Bonding Ability of TMU and DMDPU

  • 발행 : 1998.01.20
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초록

The hydrogen-bonding interactions between thioacetamide (TA) and urea derivatives such as tetramethylurea (TMU) and dimethyldiphenylurea (DMDPU) have been studied using near-infrared absorption spectroscopy. Thermodynamic parameters for the interactions between TA and urea derivatives were determined by analyzing the $v^{as}_{N-H}$+Amide Ⅱ combination band of TA at 1970 nm. The ΔH° values, indicating the intrinsic strength of hydrogen bonding, are - 23.0 kJ/mole and - 19.8 kJ/mol for TMU and DMDPU, respectively. This is well explained by the inductive effects of substituents. Ab initio molecular orbital calculations for the proton affinity of TMU, N,N-dimethylformamide (DMF), and N,N-dimethylacetamide (DMA) in gas phase have been carried out at HF/3-21G ad HF/6-31G(d) levels, showing that the proton affinity of TMU is larger than that of DMA, which agrees well the experimental results.

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