The transmission of polar effects. Part VIII. Esterification with diazodiphenylmethane and the ionization of ortho-substituted trans-cinnamic, phenoxyacetic, 3-phenylpropionic, cis- and trans-α-phenylcinnamic acids | Zendy

Keith Bowden | Zendy; D. C. Parkin | Zendy

Open Access

The transmission of polar effects. Part VIII. Esterification with diazodiphenylmethane and the ionization of ortho-substituted trans-cinnamic, phenoxyacetic, 3-phenylpropionic, cis- and trans-α-phenylcinnamic acids

Author(s) -

Keith Bowden,

D. C. Parkin

Publication year - 1968

Publication title -

canadian journal of chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.323

H-Index - 68

eISSN - 1480-3291

pISSN - 0008-4042

DOI - 10.1139/v68-645

Subject(s) - chemistry , cinnamic acid , substituent , polar , ethanol , stereochemistry , cis–trans isomerism , medicinal chemistry , organic chemistry , physics , astronomy

The rate coefficients for the esterification with diazodiphenylmethane in ethanol at 30° and the pK a values at 25° of a number of ortho-substituted trans-cinnamic, phenoxyacetic, 3-phenylpropionic, ortho-, meta-, and para-substituted cis-trans-α-phenylcinnamic acids have been determined. The effects of substitution have been assessed by a Hammett-type correlation. A comparison of the transmission of the polar effects of ortho and meta/para substituents indicates the prime importance of the field effect, augmented where possible by a π-inductive effect. A reversed dipolar substituent field effect has been detected for the cis-ortho-substituted cinnamic acids.

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