EFFECTS OF THE SUBSTITUENT GROUPS ON THE REACTION MECHANISM OF THE THERMAL DECOMPOSITION OF DIAZO ALDEHYDES: A COMPUTATIONAL STUDY

Journal of Applied Chemical Science International

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Title EFFECTS OF THE SUBSTITUENT GROUPS ON THE REACTION MECHANISM OF THE THERMAL DECOMPOSITION OF DIAZO ALDEHYDES: A COMPUTATIONAL STUDY
 
Creator CASTRO, MANUELA
RUIZ, PABLO
QUIJANO, JAIRO
 
Description A computational study on the decomposition reaction of a series of diazo aldehydes (CHO-CRN2), with the groups R=H, CH3, phenyl, i-C3H7, cyclo-C3H5, NH2, Cl and OH has been carried out. Optimization and frequency calculations on anti and syn isomers have been performed at the MP2/6-31G(d) level of theory. Based on the results, the reaction mechanism for each compound was interpreted from the possible interactions of the substituent groups with the intermediate and its influence on the reaction rate. The reaction for almost all substituents used proceeded by Wolff rearrangement in two steps, the first of them being the rate-determining step. Substituents groups with a giver capacity of π charge, such as NH2 and OH, improve the rate of decomposition of diazo aldehydes. The bonding characteristics of all the species involved in some of the studied reactions have been investigated by the natural bond orbital (NBO) analysis.
 
Publisher International Knowledge Press
 
Date 2018-02-12
 
Type info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
 
Format application/pdf
application/pdf
 
Identifier http://www.ikprress.org/index.php/JACSI/article/view/4120
 
Source Journal of Applied Chemical Science International; 2017 - Volume 8 [Issue 4]; 128-136
2395-3713
 
Language eng
 
Relation http://www.ikprress.org/index.php/JACSI/article/view/4120/3894
http://www.ikprress.org/index.php/JACSI/article/view/4120/3893
 
Rights Copyright (c) 2018 © Copyright International Knowledge Press. All rights reserved.
 

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