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Quantum Mechanical Calculations of Electrical Effects of Substituents in para-Substituted Anilines

Roberts, John D. and Semenow, Dorothy A. (1955) Quantum Mechanical Calculations of Electrical Effects of Substituents in para-Substituted Anilines. Journal of the American Chemical Society, 77 (11). pp. 3152-3153. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20151021-142339309

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Abstract

Base strength measurements with substituted anilines indicate direct conjugation between the amino groups and electron-attracting unsaturated substituent groups such as —NO_2,—C≡N, etc. (I). Such conjugation delocalizes the unshared electron pair of nitrogen and confers a formal (+) charge on the amino group. Somewhat analogous behavior might be anticipated for substituents which do not carry multiple bonds but which, like tercovalent boron, could accept an electron pair (II) or, like a positively charged trimethylammonium group, could stabilize an adjacent negatively charged center as in the “ylides” (III). Resonance forms may be written which symbolize each of these situations (I-III).


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja01616a080DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja01616a080PublisherArticle
Additional Information:© 1955 American Chemical Society. Received October 28, 1954.
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Other Numbering System NameOther Numbering System ID
Caltech Gates and Crellin Laboratories of Chemistry1953
Issue or Number:11
Record Number:CaltechAUTHORS:20151021-142339309
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20151021-142339309
Official Citation:Quantum Mechanical Calculations of Electrical Effects of Substituents in para-Substituted Anilines John D. Roberts and Dorothy A. Semenow Journal of the American Chemical Society 1955 77 (11), 3152-3153 DOI: 10.1021/ja01616a080
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61396
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:22 Oct 2015 18:20
Last Modified:03 Oct 2019 09:07

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