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Understanding thio-effects in simple phosphoryl systems: role of solvent effects and nucleophile charge
Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Cell and Molecular Biology. Uppsala University, Science for Life Laboratory, SciLifeLab.
Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Cell and Molecular Biology. Uppsala University, Science for Life Laboratory, SciLifeLab.
2015 (English)In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 13, no 19, 5391-5398 p.Article in journal (Refereed) Published
Abstract [en]

Recent experimental work (J. Org. Chem., 2012, 77, 5829) demonstrated pronounced differences in measured thio-effects for the hydrolysis of (thio) phosphodichloridates by water and hydroxide nucleophiles. In the present work, we have performed detailed quantum chemical calculations of these reactions, with the aim of rationalizing the molecular bases for this discrimination. The calculations highlight the interplay between nucleophile charge and transition state solvation in S(N)2(P) mechanisms as the basis of these differences, rather than a change in mechanism.

Place, publisher, year, edition, pages
2015. Vol. 13, no 19, 5391-5398 p.
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:uu:diva-256560DOI: 10.1039/c5ob00309aISI: 000354205600012PubMedID: 25797408OAI: oai:DiVA.org:uu-256560DiVA: diva2:825880
Funder
Swedish National Infrastructure for Computing (SNIC), 25/2-10
Available from: 2015-06-24 Created: 2015-06-24 Last updated: 2017-12-04Bibliographically approved

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Kamerlin, Shina C. L.

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