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Matsson, Olle
Alternative names
Publications (10 of 18) Show all publications
Sawadjoon, S., Sjöberg, P. J., Orthaber, A., Matsson, O. & Samec, J. S. (2014). Mechanistic Insights into the Pd-Catalyzed Direct Amination of Allyl Alcohols: Evidence for an Outer-sphere Mechanism Involving a Palladium Hydride Intermediate. Chemistry - A European Journal, 20(6), 1520-1524
Open this publication in new window or tab >>Mechanistic Insights into the Pd-Catalyzed Direct Amination of Allyl Alcohols: Evidence for an Outer-sphere Mechanism Involving a Palladium Hydride Intermediate
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2014 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 20, no 6, p. 1520-1524Article in journal (Refereed) Published
Abstract [en]

The mechanism of direct amination of allyl alcohol by a palladium triphenylphosphite complex has been explored. Labelling studies show that the reaction proceeds through a π-allylpalladium intermediate. A second-order dependence of reaction rate on allyl alcohol concentration was observed. Kinetic isotope effect studies and ESI-MS studies are in agreement with a reaction proceeding through a palladium hydride intermediate in which both O-H bond and C-O bond cleavages are involved in rate-determining steps. A stereochemical study supports an outer-sphere nucleophilic attack of the π-allylpalladium intermediate giving complete chiral transfer from starting material to product.

National Category
Analytical Chemistry Physical Chemistry
Identifiers
urn:nbn:se:uu:diva-215613 (URN)10.1002/chem.201303431 (DOI)000337300000008 ()24403056 (PubMedID)
Available from: 2014-01-15 Created: 2014-01-15 Last updated: 2017-12-06Bibliographically approved
Matsson, O. (2013). Från opium till radjaidjah. In: Björn Wahlberg (Ed.), Tintinism: Årsbok 2013 (pp. 73-82). Solna: Generation T - Den svenska Tintinföreningen i samarbete med Asterion Media
Open this publication in new window or tab >>Från opium till radjaidjah
2013 (Swedish)In: Tintinism: Årsbok 2013 / [ed] Björn Wahlberg, Solna: Generation T - Den svenska Tintinföreningen i samarbete med Asterion Media , 2013, p. 73-82Chapter in book (Other (popular science, discussion, etc.))
Place, publisher, year, edition, pages
Solna: Generation T - Den svenska Tintinföreningen i samarbete med Asterion Media, 2013
Series
Tintinism, ISSN 2000-6640 ; 6
Keywords
Gift, giftmord, skönlitteratur
National Category
General Literature Studies Natural Sciences
Identifiers
urn:nbn:se:uu:diva-223767 (URN)9789185083053 (ISBN)
Available from: 2014-04-24 Created: 2014-04-24 Last updated: 2014-04-24
Matsson, O. (2013). Gifter från växter och djur: Några exempel från kriminallitteraturen. Biologen, 78(4), 16-20
Open this publication in new window or tab >>Gifter från växter och djur: Några exempel från kriminallitteraturen
2013 (Swedish)In: Biologen, ISSN 0345-1127, Vol. 78, no 4, p. 16-20Article in journal (Other (popular science, discussion, etc.)) Published
Place, publisher, year, edition, pages
Stockholm: Biologilärarnas förening, 2013
Keywords
Gift, giftmord, skönlitteratur
National Category
General Literature Studies Natural Sciences
Identifiers
urn:nbn:se:uu:diva-223763 (URN)
Available from: 2014-04-24 Created: 2014-04-24 Last updated: 2014-08-13Bibliographically approved
Matsson, O. (2013). Giftig läsning i böckernas värld. Läkartidningen, 110(34-35), 1484-1486
Open this publication in new window or tab >>Giftig läsning i böckernas värld
2013 (Swedish)In: Läkartidningen, ISSN 0023-7205, E-ISSN 1652-7518, Vol. 110, no 34-35, p. 1484-1486Article in journal (Other (popular science, discussion, etc.)) Published
Place, publisher, year, edition, pages
Stockholm: Sveriges läkarförbund, 2013
Keywords
Gift, giftmord, skönlitteratur
National Category
General Literature Studies Natural Sciences
Identifiers
urn:nbn:se:uu:diva-223761 (URN)
Available from: 2014-04-24 Created: 2014-04-24 Last updated: 2017-12-05Bibliographically approved
Matsson, O. (2013). Inte bara arsenik: Om gifter och giftmord i kriminallitteraturen. Bokvennen, 25(1), 56-63
Open this publication in new window or tab >>Inte bara arsenik: Om gifter och giftmord i kriminallitteraturen
2013 (Swedish)In: Bokvennen, ISSN 0802-1953, Vol. 25, no 1, p. 56-63Article in journal (Other (popular science, discussion, etc.)) Published
Place, publisher, year, edition, pages
Oslo: Bokvennen Forlag AS, 2013
Keywords
Gift, giftmord, skönlitteratur
National Category
General Literature Studies Natural Sciences
Identifiers
urn:nbn:se:uu:diva-223764 (URN)
Available from: 2014-04-24 Created: 2014-04-24 Last updated: 2017-12-05Bibliographically approved
Matsson, O. (2012). En dos stryknin: Om gifter och giftmord i litteraturen. Stockholm: Bokförlaget Atlantis
Open this publication in new window or tab >>En dos stryknin: Om gifter och giftmord i litteraturen
2012 (Swedish)Book (Other (popular science, discussion, etc.))
Place, publisher, year, edition, pages
Stockholm: Bokförlaget Atlantis, 2012. p. 357
National Category
Languages and Literature Natural Sciences
Identifiers
urn:nbn:se:uu:diva-215754 (URN)978-91-7353-589-2 (ISBN)
Available from: 2014-01-16 Created: 2014-01-16 Last updated: 2014-01-16Bibliographically approved
Matsson, O. (2012). Mordisk litteratur generöst tryfferad med gift. Upsala nya tidning, 122(342)
Open this publication in new window or tab >>Mordisk litteratur generöst tryfferad med gift
2012 (Swedish)In: Upsala nya tidning, Vol. 122, no 342Article in journal, News item (Other (popular science, discussion, etc.)) Published
Place, publisher, year, edition, pages
Uppsala: , 2012
Keywords
Gift, giftmord, skönlitteratur
National Category
General Literature Studies Natural Sciences
Identifiers
urn:nbn:se:uu:diva-223760 (URN)
Available from: 2014-04-24 Created: 2014-04-24 Last updated: 2014-08-13Bibliographically approved
MacMillar, S., Fang, Y.-r., Westaway, K. C., Matsson, O. & Beronius, P. (2008). Solvent effects on ion pairing of tetra-n-butylammonium cyanide: A conductometric study. Journal of Physical Organic Chemistry, 21(3), 237-241
Open this publication in new window or tab >>Solvent effects on ion pairing of tetra-n-butylammonium cyanide: A conductometric study
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2008 (English)In: Journal of Physical Organic Chemistry, ISSN 0894-3230, E-ISSN 1099-1395, Vol. 21, no 3, p. 237-241Article in journal (Refereed) Published
Abstract [en]

Tetra-n-butylammonium cyanide (n-Bu4NCN) is a commonly used reagent, for example, for the synthesis of nitriles. Recently n-Bu4NCN has been used as the nucleophilic reagent in kinetic isotope effect studies of nucleophilic aliphatic substitution reactions. The present research concerns the aggregation status (dissociated ions, ion pairs, higher aggregates) and transport properties of n-Bu4NCN in water, dimethyl sulfoxide (DMSO), and tetrahydrofuran (THF), at 25 C as studied by means of precision conductometry. These properties are of great importance since both non-polar and dipolar aprotic solvents are commonly used in the applications. In water as solvent the equilibrium constant for ion-pair formation, K-p =10.1 and the limiting molar conductivity, Lambda(o)= 102.4 cm(2) Omega(-1) mol(-1). The corresponding values for DMSO are K-p =1.98 +/- 0.19 and Lambda(o) = 34.59 +/- 0.03 cm(2) Omega(-1) mol(-1). These data imply that the degree of dissociation, in contrast to the expectations, is higher in DMSO than in water at the same salt concentration. In THF, the conductance as a function of concentration shows a minimum typical for solvents with low relative permittivity, indicating the formation of higher aggregates. The equilibrium constant for ion-pair formation and conductivity in THF is K-p=58.4 X 10(3) and Lambda(o)=9.81 cm(2) Omega(-1) mol(-1).

Keywords
conductometry, ion pairs, solvent effect, tetra-n-butylammonium cyanide, DMSO, THF
National Category
Chemical Sciences
Identifiers
urn:nbn:se:uu:diva-15635 (URN)10.1002/poc.1305 (DOI)000253690100009 ()
Available from: 2008-02-27 Created: 2008-02-27 Last updated: 2017-12-08Bibliographically approved
Westaway, K. C., Fang, Y.-r., MacMillar, S., Matsson, O., Poirier, R. A. & Islam, S. M. (2007). A New Insight into Using Chlorine Leaving Group and Nucleophile Carbon Kinetic Isotope Effects To Determine Substituent Effects on the Structure of SN2 Transition States. Journal of Physical Chemistry A, 111(33), 8110-8120
Open this publication in new window or tab >>A New Insight into Using Chlorine Leaving Group and Nucleophile Carbon Kinetic Isotope Effects To Determine Substituent Effects on the Structure of SN2 Transition States
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2007 (English)In: Journal of Physical Chemistry A, ISSN 1089-5639, E-ISSN 1520-5215, Vol. 111, no 33, p. 8110-8120Article in journal (Refereed) Published
Abstract [en]

Chlorine leaving group k(35)/k(37), nucleophile carbon k(11)/k(14), and secondary alpha-deuterium [(k(H)/k(D))(alpha)] kinetic isotope effects (KIEs) have been measured for the S(N)2 reactions between para-substituted benzyl chlorides and tetrabutylammonium cyanide in tetrahydrofuran at 20 degrees C to determine whether these isotope effects can be used to determine the substituent effect on the structure of the transition state. The secondary alpha-deuterium KIEs indicate that the transition states for these reactions are unsymmetric. The theoretical calculations at the B3LYP/aug-cc-pVDZ level of theory support this conclusion; i.e., they suggest that the transition states for these reactions are unsymmetric with a long NC-C-alpha and reasonably short C-alpha-Cl bonds. The chlorine isotope effects suggest that these KIEs can be used to determine the substituent effects on transition state structure with the KIE decreasing when a more electron-withdrawing para-substituent is present. This conclusion is supported by theoretical calculations. The nucleophile carbon k(11)/k(14) KIEs for these reactions, however, do not change significantly with substituent and, therefore, do not appear to be useful for determining how the NC-C-alpha transition-state bond changes with substituent. The theoretical calculations indicate that the NC-C-alpha bond also shortens as a more electron-withdrawing substituent is placed on the benzene ring of the substrate but that the changes in the NC-C-alpha transition-state bond with substituent are very small and may not be measurable. The results also show that using leaving group and nucleophile carbon KIEs to determine the substituent effect on transition-state structure is more complicated than previously thought. The implication of using both chlorine leaving group and nucleophile carbon KIEs to determine the substituent effect on transition-state structure is discussed.

National Category
Chemical Sciences
Identifiers
urn:nbn:se:uu:diva-95361 (URN)10.1021/jp0729765 (DOI)000248758800010 ()
Available from: 2007-01-05 Created: 2007-01-05 Last updated: 2017-12-14Bibliographically approved
Matsson, O. & MacMillar, S. (2007). Isotope effects for fluorine-18 and carbon-11 in the study of reaction mechanism. Journal of labelled compounds & radiopharmaceuticals, 50(11-12), 982-988
Open this publication in new window or tab >>Isotope effects for fluorine-18 and carbon-11 in the study of reaction mechanism
2007 (English)In: Journal of labelled compounds & radiopharmaceuticals, ISSN 0362-4803, E-ISSN 1099-1344, Vol. 50, no 11-12, p. 982-988Article, review/survey (Refereed) Published
Abstract [en]

The use of kinetic isotope effects (KIEs) for the short-lived radionuclides 11C and 18F in the study of reaction mechanisms is described using some examples. Leaving group fluorine KIEs (k 18/k19) have been utilized to determine the rate-limiting step for nucleophilic aromatic substitution reactions (SNAr). The fluorine KIE was also used to probe the effect of changing solvent and nucleophile steric hindrance on rate-limiting step. The mechanism for a base promoted elimination reaction was determined to be stepwise (E1cB) by a multiple KIE study including the leaving group fluorine KIE. The transition state structures for aliphatic nucleophilic substitution reactions (SN2) have been investigated by multiple KIE studies for cases where the substrate substitution, leaving group or solvent has been varied. Carbon KIEs for labelled α-carbon atom in the substrate are large, k11/k14 = 1.189-1.220. For labelled nucleophile cyanide ion. k11/k 14 = 0.99951-1.0119.

Keywords
short-lived radionuclide, kinetic isotope effect, reaction mechanism, SN2, SNAr
National Category
Chemical Sciences
Identifiers
urn:nbn:se:uu:diva-12834 (URN)10.1002/jlcr.1443 (DOI)000252229400005 ()
Available from: 2008-01-17 Created: 2008-01-17 Last updated: 2017-12-11Bibliographically approved
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