Conformational-dependent reaction mechanism: case of acid hydrolysis ofN-benzoyl-9-azabicyclo[6.1.0]non-4-ene

Autor:	Ali Rahmouni, Okkacha Bensaid, Néji Besbes, Djallila Missaoui
Rok vydání:	2017
Předmět:	Quantum chemical Reaction mechanism 010405 organic chemistry Organic Chemistry Solvation Sulfuric acid General Chemistry 010402 general chemistry 01 natural sciences Catalysis 0104 chemical sciences Gas phase chemistry.chemical_compound chemistry Organic chemistry Acid hydrolysis Ene reaction
Zdroj:	Canadian Journal of Chemistry. 95:37-44
ISSN:	1480-3291 0008-4042
DOI:	10.1139/cjc-2016-0278
Popis:	Quantum chemical studies of the acid hydrolysis of cis-cis-N-benzoyl-9-azabicyclo[6.1.0]non-4-ene in gas phase and sulfuric acid solution have been carried out. Conformational analysis of reactant and intermediates were done at DFT level of calculations, using different basis sets. Transition states were identified and IRC calculations were done at the same level. In the first step of the reaction, the protonation occurs preferentially on the nitrogen atom. Three products are obtained. The type of mechanism, stepwise or concerted, depends on the stable conformers and the cleaved N–C bond. The main conclusion is that the products of the reaction depend on the nature of the stable conformer of the reactant.
Databáze:	OpenAIRE
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