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Substituent effects on the addition of alcohols and anilines to organic isothiocyanates

Rao, CNR and Venkataraghavan, R (1963) Substituent effects on the addition of alcohols and anilines to organic isothiocyanates. In: Tetrahedron, 19 (10). pp. 1509-1518.

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Official URL: http://dx.doi.org/10.1016/S0040-4020(01)99224-5


The addition reactions of alcohols, ROH (R = CH3, C2H5 n-C3H7, i-C3H7 and t-C4H9), to p-bromophenylisothiocyanate show that the rates decrease in the order, CH3OH> C2H5OH> n-C3H7OH> i-C3H7OH> t-C4H9OH, although the basicities of the alcohols vary in the reverse order. The results indicate the greater importance of steric factors as compared with polar factors. Evidence is also presented for the formation of a complex between the isothiocyanate and the alcohol in the first stage of the addition reaction. In the addition of aniline to substituted phenylisothiocyanates the rate data give a satisfactory linear correlation with Hammett σ constants and the results clearly show that electron-withdrawing groups favour the addition reaction. The addition of aniline to alkyl isothiocyanates have been studied in order to find out the nature of alkyl group interaction in these derivatives. Kinetic studies on the addition of substituted anilines to phenylisothiocyanate show that the rate of reaction increases with the electron-donating ability of the substituents on the aniline as also the basicity of the aniline.

Item Type: Journal Article
Publication: Tetrahedron
Publisher: Elsevier Science
Additional Information: Copyright of this article belongs to Elsevier Science.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Division of Chemical Sciences > Inorganic & Physical Chemistry
Date Deposited: 25 May 2010 06:25
Last Modified: 19 Sep 2010 06:07
URI: http://eprints.iisc.ac.in/id/eprint/28125

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