Abstract

The study of proton shift behavior in nine families of disubstituted benzenes has provided quantitative correlations of internal and meta shifts among all families. The equations of correlation are useful in the prediction of shifts to an error of 0.015 ppm. The studies demonstrate shift additivity for the 4-substituted halobenzenes and suggest a chain rule relationship for substituent effects in those compounds. For that reason, previous theories of substituent interactions involving inductive and resonance contributors appear incorrect when applied to proton shift data. In decreasing order of up field shift at the ortho protons the substituents studied include N(CH3)2, NH2, OCH3, OH, F, CH3, CH2CH3, H, Cl, C(CH3)3, Br, CN, COOCH3, COOH, COCI, NO2. © 1973, American Chemical Society. All rights reserved.

Department(s)

Chemistry

International Standard Serial Number (ISSN)

1520-5126; 0002-7863

Document Type

Article - Journal

Document Version

Citation

File Type

text

Language(s)

English

Rights

© 2023 American Chemical Society, All rights reserved.

Publication Date

01 Aug 1973

Included in

Chemistry Commons

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