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Journal of the Mexican Chemical Society

Print version ISSN 1870-249X

J. Mex. Chem. Soc vol.52 n.4 Ciudad de México Oct./Dec. 2008




Theoretical Study of Reactivity Based on the Hard–Soft/Acid–base (HSAB) in Isatoic Anhydride and Some Derivatives


Fernando R. Ramos–Morales,1* Sergio Durand–Niconoff,2 José Correa–Basurto,3 Francisco J. Meléndez–Bustamante,4 and J. Samuel Cruz–Sánchez2


1 Unidad de Servicios de Apoyo en Resolución Analítica, Universidad Veracruzana. Luis Castelazo Ayala s/n Col. Industrial Animas 91190, phone +52 2288 418900 (13553) Xalapa, Ver., México. *Responsible author:

2 Instituto de Ciencias Básicas, Universidad Veracruzana. Xalapa, Veracruz. México.

3 Departamento de Farmacología y SEPI, Escuela Superior de Medicina, Instituto Politécnico Nacional, Mexico 11340, D.F.

4 Departamento de Fisicoquímica, Facultad de Ciencias Químicas, BUAP Edif. 139. Ciudad Universitaria, Puebla, Pue., 72570, México.


Received June 13, 2008
Accepted November 19, 2008



In order to utilize the great chemical potential of isatoic anhidryde (ISA) as a precursor of several derived products, it was most important to determine its molecular reactivity. To this end, we have carried out theoretical calculations on ISA and some of its derivatives by using density functional theory (DFT), MP2, HF levels of theory with a correlated augmented basis set aug–cc–pvDZ. The B3LYP/aug–cc–pvDZ level yielded theoretical results that correlated very well with the experimental work. We used this method to get the global and local descriptors with Koopman's approximation, taking into account two main ISA structural components: the aromatic and heterocyclic systems. The Fukui functions were calculated on the formalism of the quantum theory of atoms in molecules (QTAIM) which is a method for condensation. These theoretical calculations allow to study the electron–withdrawing or donating substituent of the aromatic ring. The results showed that, globally, the most reactive compound is ISA with the OCH3 substituent. Locally, it is confirmed that C2 is the molecular region most susceptible to suffer a nucleophilic attack against ISA.

Key words: Isatoic anhydride (ISA), molecular reactivity, Fukui functions, nucleophilic attack, electrophilic attack.



Con la finalidad de utilizar el gran potencial químico del anhídrido isatoico (ISA) como precursor de varios derivados, es importante determinar su reactividad molecular. En ese sentido, llevamos a cabo cálculos teóricos del ISA y algunos de sus derivados usando métodos de la Teoría de Funcionales de la Densidad (DFT), MP2, HF con bases de correlación aumentadas aug–cc–pvDZ. El método B3LYP/aug–cc–pvDZ proporcionó resultados teóricos que correlacionaron muy bien con el trabajo experimental. Utilizamos este método para obtener los descriptores globales y locales con la aproximación de Koopman, tomando en cuenta dos componentes estructurales del ISA: los sistemas aromático y heterocíclico. Las funciones de Fukui fueron calculadas con base al formalismo de la teoría cuántica de átomos en moléculas (TCAEM) que es un método para condensación. Estos cálculos teóricos permitieron estudiar sustituyentes electrodonadores y electroatractores en el anillo aromático. Los resultados mostraron que, globalmente, el compuesto más reactivo es ISA con el sustituyente OCH3. Localmente, se confirmó que C2 es la región molecular más susceptible de sufrir un ataque nucleofílico en relación al ISA.

Palabras clave: Anhidrido isatoico (ISA), reactividad molecular, funciones de Fukui, ataque nucleofílico, ataque electrofílico.





This work was supported by grants from PROMEP PTC–249 to FRRM, CONACYT–Mexico (62488 to JCB; II–52959 to FJMB). The authors thanks to Irene Marquina S. and Warren Haid for review this manuscript.


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