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The aminolysis of phosphinates; the kinetics and mechanism of the aminolysis of phosphinate esters in acetonitrile

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dc.contributor.author Kabbani, Ahmad
dc.contributor.author Cook, Robert D.
dc.contributor.author Samaha, Muna
dc.contributor.author Daouk, Wafa A
dc.contributor.author Hajj, Asaad N.
dc.contributor.author Shayban, Fuad
dc.contributor.author Tanelian, Ohannes V.
dc.date.accessioned 2016-03-15T09:43:58Z
dc.date.available 2016-03-15T09:43:58Z
dc.date.copyright 1986
dc.date.issued 2016-03-15
dc.identifier.issn 0008-4042 en_US
dc.identifier.uri http://hdl.handle.net/10725/3329
dc.description.abstract The aminolysis of aryl diphenylphosphinates, p-nitrophenyl diphenylphosphinothionate, -phosphinothioate, and -phosphinodithioate by n-butylamine, by the secondary amines piperidine, pyrrolidine, morpholine, and dipropylamine, as well as by a series of diamines, has been studied in acetonitrile. The general reactivity order is diamines > butylamine > sec-amines. Butylaminolysis follows a two-term rate law, one first order in amine and the other second order in amine. The second order in amine term predominates. sec-Amines and diamines follow a rate law which is first order in amine only. Leaving group effects, solvent effects, and activation parameters support a pathway which involves rate-determining collapse of a zwitterionic pentacoordinate intermediate. In the case of butylamine this collapse is general base catalyzed and for the diamines the reaction is intramolecularly general base catalyzed. en_US
dc.language.iso en en_US
dc.title The aminolysis of phosphinates; the kinetics and mechanism of the aminolysis of phosphinate esters in acetonitrile en_US
dc.type Article en_US
dc.description.version Published en_US
dc.author.school SAS en_US
dc.author.idnumber 198029470 en_US
dc.author.woa N/A en_US
dc.author.department Natural Sciences en_US
dc.description.embargo N/A en_US
dc.relation.journal Canadian Journal of Chemistry en_US
dc.journal.volume 64 en_US
dc.journal.issue 2 en_US
dc.article.pages 213-219 en_US
dc.identifier.ctation Cook, R. D., Daouk, W. A., Hajj, A. N., Kabbani, A., Kurku, A., Samaha, M., ... & Tanielian, O. V. (1986). The aminolysis of phosphinates; the kinetics and mechanism of the aminolysis of phosphinate esters in acetonitrile. Canadian journal of chemistry, 64(2), 213-219. en_US
dc.author.email akabbani@lau.edu.lb
dc.identifier.url http://www.nrcresearchpress.com/doi/abs/10.1139/v86-037#.V5mw3rh97y0


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