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Use of 15N Label in Organic Synthesis and Spectroscopy. Part I: Preparation of 15N-Labeled tert-Butylamine

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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

J. Chem. Educ., 2002, 79 (2), p 221

DOI: 10.1021/ed079p221

Publication Date (Web): February 1, 2002

Section:

History, Education, and Documentation

Abstract

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.

Keywords (Audience):

Upper-Division Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

IR Spectroscopy

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This article has been cited by 1 ACS Journal articles (1 most recent appear below).

In Situ¹H NMR Studies of High-Temperature Nitroxide-Mediated Polymerization of n-Butyl Acrylate
Lebohang Hlalele and Bert Klumperman
Macromolecules2011 44 (18), 7100-7108
- In Situ¹H NMR Studies of High-Temperature Nitroxide-Mediated Polymerization of n-Butyl Acrylate
  Lebohang Hlalele and Bert Klumperman
  Macromolecules2011 44 (18), 7100-7108
  This paper presents results on the independence of the rate of polymerization of n-butyl acrylate (n-BA) toward initial concentration of the alkoxyamine initiator. The alkoxyamine, 2-methyl-2-[N-tert-butyl-N-(1-diethoxyphosphoryl-2,2-dimethylpropyl)...
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Received: August 03, 2009

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Article

Use of 15N Label in Organic Synthesis and Spectroscopy. Part I: Preparation of 15N-Labeled tert-Butylamine