Kinetic study of solvent effects on the aminolysis of O-ethyl S-aryl dithiocarbonates

2012 ◽  
Vol 25 (11) ◽  
pp. 989-993 ◽  
Author(s):  
Daniela Millán ◽  
José G. Santos ◽  
Enrique A. Castro
Keyword(s):  
Kinetic Study ◽  
Solvent Effects

scholarly journals Synergistic Experimental and Computational Investigation of the Bioorthogonal Reactivity of Substituted Aryltetrazines

2021 ◽  
Author(s):  
Umberto Battisti ◽  
Rocío García-Vázquez ◽  
Dennis Svatunek ◽  
Barbara Herrmann ◽  
Andreas Löffler ◽  
...  
Keyword(s):  
Kinetic Study ◽  
Solvent Effects ◽  
Rate Constants ◽  
Biomedical Applications ◽  
Aqueous Systems ◽  
Phenyl Substituent ◽  
Computational Investigation ◽  
Radiation Burden ◽  
Intrinsic Reactivity

Tetrazines (Tz) have been applied as bioorthogonal agents for various biomedical applications including pretargeted imaging approaches. In radioimmunoimaging, pretargeting increases the target-to-background ratio while simultaneously reducing the radiation burden. We have recently reported a strategy to directly 18F-label highly reactive tetrazines based on a 3-(3-fluorophenyl)-Tz core structure. Herein, we report a kinetic study on this versatile scaffold. A library of 40 different tetrazines was prepared, fully characterized, and investigated with emphasis on second order rate constants for the reaction with trans-cyclooctene (TCO). Our results reveal the effects of various substitution patterns and moreover demonstrate the importance of measuring reactivities in the solvent of interest, as click rates in different solvents do not necessarily correlate well. In particular, we report that tetrazines modified in 2-position of the phenyl substituent show high intrinsic reactivity towards TCO, which is diminished in aqueous systems by unfavorable solvent effects. The obtained results enable the prediction of the bioorthogonal reactivity and thereby facilitate the development of the next-generation of substituted aryltetrazines for in vivo application.

Kinetic study of thermolysis of diarylhomonaphthoquinones. Endo/exo substituent and solvent effects

2000 ◽  
pp. 135-141 ◽  
Author(s):  
Takumi Oshima ◽  
Kazushi Tamada ◽  
Hatsue Tamura ◽  
Toshikazu Nagai
Keyword(s):  
Kinetic Study ◽  
Solvent Effects

Comparative kinetic study of solvent effects in the reactions of 1,2-dinitrobenzene with butylamine and piperidine

1989 ◽  
Vol 2 (8) ◽  
pp. 631-645 ◽  
Author(s):  
S. M. Chiacchiera ◽  
R. I. Cattana ◽  
J. O. Singh ◽  
J. D. Anunziata ◽  
J. J. Silber
Keyword(s):  
Kinetic Study ◽  
Solvent Effects

ChemInform Abstract: Kinetic Study of Thermolysis of Diarylhomonaphthoquinones. endo/exo Substituent and Solvent Effects.

ChemInform ◽  
2010 ◽  
Vol 31 (15) ◽  
pp. no-no
Author(s):  
Takumi Oshima ◽  
Kazushi Tamada ◽  
Hatsue Tamura ◽  
Toshikazu Nagai
Keyword(s):  
Kinetic Study ◽  
Solvent Effects
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