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ERIC Number: EJ1082428
Record Type: Journal
Publication Date: 2015-Nov
Pages: 7
Abstractor: As Provided
ISSN: ISSN-0021-9584
Electrostatic Potential Maps and Natural Bond Orbital Analysis: Visualization and Conceptualization of Reactivity in Sanger's Reagent
Mottishaw, Jeffery D.; Erck, Adam R.; Kramer, Jordan H.; Sun, Haoran; Koppang, Miles
Journal of Chemical Education, v92 n11 p1846-1852 Nov 2015
Frederick Sanger's early work on protein sequencing through the use of colorimetric labeling combined with liquid chromatography involves an important nucleophilic aromatic substitution (S[subscript N]Ar) reaction in which the N-terminus of a protein is tagged with Sanger's reagent. Understanding the inherent differences between this S[subscript N]Ar reaction and other nucleophilic substitution reactions (S[subscript N]1 and S[subscript N] 2) can be challenging for students learning organic chemistry. Here, both electrostatic potential (ESP) maps and natural bond orbital (NBO) analyses are employed to visualize and conceptualize Sanger's key observation of the difference in reactivity between 2,4-dinitrochlorobenzene and 2,4-dinitrofluorobenzene. The utility of this method is extended to compare the reactivity of a series of halobenzenes for S[subscript N]Ar fluorination, a widely used reaction in pharmaceutical and medicinal fields. In combination with experimental results from the literature, the ESP maps and NBO analyses are consistent with and provide excellent corroboration with the reactivity of different substrates toward S[subscript N]Ar reactions.
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 (NSF)
Authoring Institution: N/A
Grant or Contract Numbers: CHE1355677; CHE1063000; DGE0903685; CHE1460872