Effect of N-alkyl and N-aralkyl substituents on nucleophilic substitution in the benzimidazole series

Autor:	M. M. Medvedeva, V. N. Novikov, Alexander F. Pozharskii, V. N. Doron'kin
Rok vydání:	1977
Předmět:	chemistry.chemical_classification Steric effects Benzimidazole Stereochemistry Organic Chemistry chemistry.chemical_element Medicinal chemistry chemistry.chemical_compound chemistry Chlorine Nucleophilic substitution SN2 reaction Piperidine Chichibabin reaction Alkyl
Zdroj:	Chemistry of Heterocyclic Compounds. 13:903-909
ISSN:	1573-8353 0009-3122
DOI:	10.1007/bf00488920
Popis:	It is shown in the case of the Chichibabin reaction and exchange of chlorine in 2-chlorobenzimidazoles by a piperidine residue that N-alkyl and N-aralkyl groups are arranged in the following order with respect to their effect on the rate of the process (in the order of decreasing rates): CH3>C6H5CH2, C2H5>iso-C3H7, (C6H5)2CH>n-C9H19>tert-C4H9. The overall decrease in the rate on passing to compounds with branched N-substituents is low. It follows from this that steric hindrance to nucleophilic substitution in the 2 position is only of small significance.
Databáze:	OpenAIRE
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