期刊
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
卷 13, 期 13, 页码 5926-5930出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c0cp02774j
关键词
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资金
- F&M Snavely Summer Research stipend
- Snavely Research Award
- William M. and Lucille M. Hackman Scholars Program
- Mellon/CPC New Tasks/New Tools
- NIH [R15GM093330]
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R15GM093330] Funding Source: NIH RePORTER
The synthesis of 2'-azido-5-cyano-2'-deoxyuridine, N(3)CNdU (1), from trityl-protected 2'-amino-2'-deoxyuridine was accomplished in four steps with a 12.5% overall yield. The IR absorption positions and profiles of the azide and nitrile group of N(3)CNdU were investigated in 14 different solvents and water/DMSO solvent mixtures. The azide probe was superior to the nitrile probe in terms of its extinction coefficient, which is 2-4 times larger. However, the nitrile IR absorbance profile is generally less complicated by accidental Fermi resonance. The IR frequencies of both probes undergo a substantial red shift upon going from water to aprotic solvents such as THF or DMSO. DFT calculations supported the hypothesis that the molecular origin of the higher observed frequency in water is primarily due to hydrogen bonds between the probes and water molecules.
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