Kinetic study of thermal 1,3-dipolar cycloaddition of azomethine ylides using differential scanning calorimetry as monitoring window
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Title: | Kinetic study of thermal 1,3-dipolar cycloaddition of azomethine ylides using differential scanning calorimetry as monitoring window |
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Authors: | Mancebo Aracil, Juan | Muñoz Guillena, María José | Such-Basañez, Ion | Sansano, Jose M. |
Research Group/s: | Procesos Catalíticos en Síntesis Orgánica | Materiales Carbonosos y Medio Ambiente |
Center, Department or Service: | Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Servicios Técnicos de Investigación |
Keywords: | Autocatalysis | Azomethine ylides | Cycloaddition | Differential scanning calorimetry | Kinetics |
Knowledge Area: | Química Orgánica |
Date Created: | 2012 |
Issue Date: | 26-Jun-2012 |
Publisher: | Wiley-VCH Verlag GmbH & Co. KGaA |
Citation: | MANCEBO-ARACIL, Juan, et al. “Kinetic study of thermal 1,3-dipolar cycloaddition of azomethine ylides using differential scanning calorimetry as monitoring window”. ChemPlusChem. Vol. 77, Issue 9 (Sept. 2012). ISSN 2192-6506, pp. 770-777 |
Abstract: | Kinetics of 1,3-dipolar cycloaddition involving azomethine ylides, generated from thermal [1,2]-prototropy of the corresponding imino ester, employing differential scanning calorimetry (DSC), is surveyed. Glycine and phenylalanine derived imino esters have different behavior. The first one prefers reacting with itself at 75 ºC, rather than with the dipolarophile. However, the α-substituted imino ester gives the cycloadduct at higher temperatures. The thermal dynamic analysis by 1H NMR of the neat reaction mixture of the glycine derivative reveals the presence of signals corresponding to the dipole in very small proportion. The non-isothermal and isothermal DSC curves of the cycloaddition of phenylalaninate and diisobutyl fumarate are obtained from freshly prepared samples. The application of known kinetic models and mathematical multiple non-linear regressions (NLR) allow to determine and to compare Ea, lnA, reaction orders, and reaction enthalpy. Finally a rate equation for each different temperature can be established for this particular thermal cycloaddition. |
Sponsor: | This work has been supported by the Spanish Ministerio de Ciencia e Innovación (MICINN) (Consolider INGENIO 2010 CSD2007-00006, CTQ2010-20387, FEDER, Generalitat Valenciana (PROMETEO/2009/039), and by the University of Alicante. |
URI: | http://hdl.handle.net/10045/24276 |
ISSN: | 2192-6506 |
DOI: | 10.1002/cplu.201200107 |
Language: | eng |
Type: | info:eu-repo/semantics/article |
Peer Review: | si |
Publisher version: | http://dx.doi.org/10.1002/cplu.201200107 |
Appears in Collections: | INV - PCSO - Artículos de Revistas INV - SINTAS - Artículos de Revistas |
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File | Description | Size | Format | |
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Chempluschem manuscript100391546.pdf | Versión revisada (acceso abierto) | 446,55 kB | Adobe PDF | Open Preview |
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