Gas phase basicity of formamidine ureas
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- Diaz David D.
- The Scripps Research Institute
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- Finn M. G.
- The Scripps Research Institute
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- Mishima Masaaki
- Kyushu Univ., IMCE
Bibliographic Information
- Other Title
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- ホルムアミジンウレア誘導体の気相塩基性度
Abstract
The gas-phase basicities (GBs) for a representative set of six formamidine ureas with variations in the imino substitutent (RN=CHN(Me)CONHMe) were determined in proton-transfer equilibria by ion cyclotron resonance (ICR) mass spectrometry and further explored with calculations at the B3LYP/6-31+G* level of theory. Relative GBs were linearly correlated to the inductive effect of the imine nitrogen substituents, giving a rohI= -33. The magnitude of the rohI value suggests that protonation occurs preferentially at the imino nitrogen. The calculated basicities for the imino N-protonated ones are in good agreement with the observed values. The GB values were also found to be similar to those previously reported for N1,N1-dimethyl-N2-substituted formamidines. These results indicate importance of intramolecular hydrogen-bonding interaction with the amide oxygen in the protonated ion.
Journal
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- Abstracts of Symposium on Physical Organic Chemistry
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Abstracts of Symposium on Physical Organic Chemistry 55 (0), 67-67, 2005
The Society of Physical Organic Chemistry, Japan
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Details 詳細情報について
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- CRID
- 1390001205554255616
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- NII Article ID
- 130004646403
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- Data Source
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- JaLC
- CiNii Articles
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- Abstract License Flag
- Disallowed