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The Discovery Approach to NMR: Development of Chemical-Shift Additivity Tables and Application to Product Identification

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Eric Bosch

Department of Chemistry, Southwest Missouri State University, Springfield, MO 65804-0087

J. Chem. Educ., 2000, 77 (7), p 890

DOI: 10.1021/ed077p890

Publication Date (Web): July 1, 2000

Abstract

A discovery-based approach to the preparation and application of chemical-shift additivity tables is presented to give students insight into the development of NMR spectral prediction software. The chemical shift of each proton in meta-dinitrobenzene is first assigned on the basis of the expected coupling constants (ortho, meta, and para) around a benzene ring. These chemical shifts are used to determine the chemical shift additivity for a nitro group ortho, meta, or para to hydrogen on a benzene nucleus. The chemical shift additivities obtained are then used to predict the NMR spectrum of the product of nitration of methylbenzoate.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Pedagogy):

Internet / Web-Based Learning

Keywords (Subject):

Laboratory Computing / Interfacing

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Citing Articles

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This article has been cited by 4 ACS Journal articles (4 most recent appear below).

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- Toward the Integration of Liquid- and Solid-State NMR across the Undergraduate Curriculum
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  2007 969 (), 20-35
  This work addresses issues of fundamental reform in the undergraduate chemistry curriculum via advanced integration of liquid- and solid-state nuclear magnetic resonance (NMR) experiments and theory. Our integrated curricula comprises a suite of NMR ...
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Incorporating Guided-Inquiry Learning into the Organic Chemistry Laboratory
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- Incorporating Guided-Inquiry Learning into the Organic Chemistry Laboratory
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A Laboratory Assignment in 1H NMR Spectroscopy: A Comparative Analysis of Calculated and Experimental 1H NMR Chemical Shifts
Susan D. Van Arnum
Journal of Chemical Education2006 83 (3), 429
- A Laboratory Assignment in 1H NMR Spectroscopy: A Comparative Analysis of Calculated and Experimental 1H NMR Chemical Shifts
  Susan D. Van Arnum
  Journal of Chemical Education2006 83 (3), 429
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  Abstract | Hi-Res PDF | PDF w/ Links
Fun with Computational Chemistry: Solving Spectral Problems Using Computed 13C NMR Chemical Shifts. A Comparison of Empirical and Quantum Mechanical Methods
David A. Forsyth , Leon J. Tilley and Shawn J. Prevoir
Journal of Chemical Education2002 79 (5), 593
- Fun with Computational Chemistry: Solving Spectral Problems Using Computed 13C NMR Chemical Shifts. A Comparison of Empirical and Quantum Mechanical Methods
  David A. Forsyth , Leon J. Tilley and Shawn J. Prevoir
  Journal of Chemical Education2002 79 (5), 593
  The viability of using 13C NMR shift prediction as an aid to solving undergraduate spectral problems was tested. The chemical shifts of structures corresponding to four typical problems were calculated on a PC using two approaches: (i) a quantum ...
  Abstract | Hi-Res PDF | PDF w/ Links