Use of 15N Label in Organic Synthesis and Spectroscopy. Part I: Preparation of 15N-Labeled tert-Butylamine
Erach R. Talaty, Christopher A. Boese, Sanni M. Adewale, Mohammed S. Ismail, Frank A. Provenzano, and Melissa J. Utz
Department of Chemistry, Wichita State University, Wichita, KS 67260-0051
The preparation of 15N-labeled tert-butylamine involves the conversion of the correspondingly labeled potassium cyanide into the 15N-labeled tert-butylformamide via the Ritter reaction in 85% yield, followed by hydrolysis with either aqueous sodium hydroxide or hydrochloric acid. The NMR spectra of the compounds provide a valuable opportunity for discussing several important topics in NMR spectroscopy, such as cis-trans isomerism due to restricted rotation and 15N coupling. Comparison of the IR spectra of the labeled and unlabeled compounds permits a forum for discussing the theory of vibrational frequencies.
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Citation
Talaty, Erach R.; Boese, Christopher A.; Adewale, Sanni M.; Ismail, Mohammed S.; Provenzano, Frank A.; Utz, Melissa J. J. Chem. Educ.2002 79 221.
Keywords
IR Spectroscopy; Laboratory Instruction; NMR Spectrometry; Organic Chemistry; Organic Synthesis
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