NotesFAQContact Us
Search Tips
Peer reviewed Peer reviewed
Direct linkDirect link
ERIC Number: EJ1062290
Record Type: Journal
Publication Date: 2015-Mar
Pages: 4
Abstractor: As Provided
Reference Count: 7
ISSN: ISSN-0021-9584
Nucleophilic Substitution Reactions Using Phosphine Nucleophiles: An Introduction to Phosphorus-31 NMR
Sibbald, Paul A.
Journal of Chemical Education, v92 n3 p567-570 Mar 2015
Nuclear magnetic resonance (NMR) spectroscopy is commonly used in modern synthetic chemistry to monitor the conversion of reactants to products. Since instruction in the use of NMR spectroscopy typically does not occur until after the introduction of nucleophilic substitution reactions, organic chemistry students are not able to take advantage of this technique to measure and quantify important concepts such as relative electrophile and nucleophile reactivity. A phosphorus-31 ([superscript 31]P) NMR spectroscopy experiment is reported that allows undergraduate students to monitor product formation for a number of different alkyl halide electrophiles and phosphorus nucleophiles. In this experiment, students are able to use reactant-to-product ratios obtained by simple [superscript 31]P NMR spectroscopy to explore the relative reactivities of these compounds. This exercise serves as an introduction to both NMR spectroscopy and the specific advantages of heteronuclear NMR spectroscopy.
Division of Chemical Education, Inc and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail:; Web site:
Publication Type: Journal Articles; Reports - Research
Education Level: Higher Education; Postsecondary Education
Audience: N/A
Language: English
Sponsor: National Science Foundation
Authoring Institution: N/A
Grant or Contract Numbers: 1044067