<?xml version="1.0" encoding="ISO-8859-1"?><article xmlns:mml="http://www.w3.org/1998/Math/MathML" xmlns:xlink="http://www.w3.org/1999/xlink" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance">
<front>
<journal-meta>
<journal-id>1870-249X</journal-id>
<journal-title><![CDATA[Journal of the Mexican Chemical Society]]></journal-title>
<abbrev-journal-title><![CDATA[J. Mex. Chem. Soc]]></abbrev-journal-title>
<issn>1870-249X</issn>
<publisher>
<publisher-name><![CDATA[Sociedad Química de México A.C.]]></publisher-name>
</publisher>
</journal-meta>
<article-meta>
<article-id>S1870-249X2020000200147</article-id>
<article-id pub-id-type="doi">10.29356/jmcs.v64i2.1111</article-id>
<title-group>
<article-title xml:lang="en"><![CDATA[Theoretical Study on the Mechanism of [3+2] Cycloaddition Reactions between &#945;,&#946;-unsaturated Selenoaldehyde with Nitrone and with Nitrile Oxide]]></article-title>
</title-group>
<contrib-group>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Mohammad-Salim]]></surname>
<given-names><![CDATA[Haydar]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
</contrib>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Hassan]]></surname>
<given-names><![CDATA[Rezan]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
</contrib>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Abdallah]]></surname>
<given-names><![CDATA[Hassan H.]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
</contrib>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Oftadeh]]></surname>
<given-names><![CDATA[Mohsen]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
</contrib>
</contrib-group>
<aff id="Af1">
<institution><![CDATA[,University of Zakho Faculty of Science Chemistry Department]]></institution>
<addr-line><![CDATA[ Duhok]]></addr-line>
<country>Iraq</country>
</aff>
<aff id="Af2">
<institution><![CDATA[,Salahaddin University-erbil college of Science Chemistry Department]]></institution>
<addr-line><![CDATA[ ]]></addr-line>
<country>Iraq</country>
</aff>
<aff id="Af3">
<institution><![CDATA[,Salahaddin University-erbil college of education Chemistry Department]]></institution>
<addr-line><![CDATA[ ]]></addr-line>
<country>Iraq</country>
</aff>
<aff id="Af4">
<institution><![CDATA[,Payame Noor University Chemistry Department ]]></institution>
<addr-line><![CDATA[Tehran ]]></addr-line>
<country>Iran</country>
</aff>
<pub-date pub-type="pub">
<day>00</day>
<month>06</month>
<year>2020</year>
</pub-date>
<pub-date pub-type="epub">
<day>00</day>
<month>06</month>
<year>2020</year>
</pub-date>
<volume>64</volume>
<numero>2</numero>
<fpage>147</fpage>
<lpage>164</lpage>
<copyright-statement/>
<copyright-year/>
<self-uri xlink:href="http://www.scielo.org.mx/scielo.php?script=sci_arttext&amp;pid=S1870-249X2020000200147&amp;lng=en&amp;nrm=iso"></self-uri><self-uri xlink:href="http://www.scielo.org.mx/scielo.php?script=sci_abstract&amp;pid=S1870-249X2020000200147&amp;lng=en&amp;nrm=iso"></self-uri><self-uri xlink:href="http://www.scielo.org.mx/scielo.php?script=sci_pdf&amp;pid=S1870-249X2020000200147&amp;lng=en&amp;nrm=iso"></self-uri><abstract abstract-type="short" xml:lang="en"><p><![CDATA[Abstract The reaction mechanisms of [3+2] cycloaddition (32CA) between the &#945;,&#946;-unsaturated selenoaldehyde with nitrone and nitrile oxide were investigated theoretically using the molecular electron density theory (MEDT). Selenoaldehyde has two unsaturations which allow for the cycloaddition occurring. It was expected to undergo four regioisomeric reaction paths in two separate reactions with nitrone and nitrile oxide. The study was conducted using ab initio approach at MP2/6-31G(d) level of theory. Potential energy surfaces were generated from the energies of the stationary points involved in the mechanisms and the dominant reaction pathways were identified. It was found that Pathway 3 and 4 are the two competing reaction channels, where the cycloaddition reaction occurs at the selenium-analogue carbonyl group of selenoaldehyde. The reactivity indices were analysed at the ground state of the reactants to predict the reactivity of studied organic molecules in 32CA reactions. Analysis of the electronic structure of nitrone and nitrile oxide, the three-atom-components (TACs), and their participation in 32CA reactions towards selenoaldehyde allows establishing a useful classification of 32CA reactions into zwitterionin-type (zw-type) reactions involving TACs with a high zwitterionic character.]]></p></abstract>
<abstract abstract-type="short" xml:lang="es"><p><![CDATA[Resumen Se estudia teóricamente, utilizando la teoría de la densidad electrónica molecular (MEDT), el mecanismo de reacción de la cicloadición [3+2] (32CA) entre selenoaldehídos &#945;, &#946; insaturados con nitrona y óxido de nitrilo. El selenoaldehído tiene dos insaturaciones que permiten la cicloadición. Se esperaba que la reacción se llevara a cabo a lo largo de cuatro caminos regioisoméricos en dos reacciones separadas con la nitrona y el óxido de nitrilo. Se realizó un estudio ab initio con el nivel de teoría MP2/6-31G(d). Se generaron superficies de energía potencial a partir de las energías de los puntos estacionarios involucrados en el mecanismo y se identificaron los caminos de reacción dominantes. Se encontró que dos rutas, la 3 y la 4, son los canales de reacción que compiten para que ocurra la cicloadición en el grupo carbonilo análogo al selenio del selenoaldheído. Se analizaron los índices de reactividad de los estados basales de los reactivos para predecir la reactividad de las moléculas orgánicas estudiadas en las reacciones 32CA. El análisis de la estructura electrónica de la nitrona y el óxido de nitrilo, de las componentes triatómicas (TACs) y de su participación en las reacciones 32CA hacia el selenoaldheído permite clasificar a las reacciones 32CA en tipo zwitteriónico (zw) que involucran a los TACs con un elevado carácter zwitteriónico.]]></p></abstract>
<kwd-group>
<kwd lng="en"><![CDATA[Selenoaldehyde]]></kwd>
<kwd lng="en"><![CDATA[nitrone]]></kwd>
<kwd lng="en"><![CDATA[nitrile oxide]]></kwd>
<kwd lng="en"><![CDATA[MP2]]></kwd>
<kwd lng="en"><![CDATA[ELF]]></kwd>
<kwd lng="en"><![CDATA[cycloaddition]]></kwd>
<kwd lng="en"><![CDATA[MEDT]]></kwd>
<kwd lng="es"><![CDATA[Selenoaldehído]]></kwd>
<kwd lng="es"><![CDATA[nitrona]]></kwd>
<kwd lng="es"><![CDATA[óxido de nitrilo]]></kwd>
<kwd lng="es"><![CDATA[MP2]]></kwd>
<kwd lng="es"><![CDATA[ELF]]></kwd>
<kwd lng="es"><![CDATA[cicloadición]]></kwd>
<kwd lng="es"><![CDATA[MEDT]]></kwd>
</kwd-group>
</article-meta>
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