A molecular electron density theory study of the Lewis acid–catalyzed decomposition reaction of nitroethyl benzoate using aluminum derivatives

K?cka‐Zych Agnieszka; Ríos‐Gutiérrez Mar; Domingo Luis R.

摘要

Abstract > The molecular mechanism of the decomposition reaction of nitroethyl benzoate (NEB‐1) catalyzed by Lewis acids (LAs) based on aluminum metal, AlMe <sub>3</sub> , and AlCl <sub>3</sub> , in N , N ‐dimethylacetamide, has been analyzed within the molecular electron density theory (MEDT) using calculations at the B3LYP(PCM)/6‐31+G(d) computational level. These LA‐catalyzed decomposition reactions take place via a two‐step mechanism involving a zwitterionic intermediate. The use of a more acidic AlCl <sub>3</sub> LA favors the decomposition reaction, both kinetically and thermodynamically. The bonding evolution theory (BET) analyses indicate that these LA‐catalyzed decomposition reactions begin with the proton transfer process, followed by the extrusion of benzoic acid at the second step of the reaction. </abstract> </span> <span class="z_kbtn z_kbtnclass hoverxs" style="display: none;">展开▼</span> </div> <div class="translation abstracttxt"> <span class="zhankaihshouqi fivelineshidden" id="abstract"> <span>机译：</span><Abstract Type =“Main”XML：Lang =“en”> <标题类型=“main”>摘要</标题> > Lewis酸催化的硝基甲酯（NEB-1）的分解反应的分子机制（LAS）基于铝金属，ALME <sub> 3 </ sub>，ALCL <sub> 3 </ sub>，在 n℃下， n / i> - 甲基乙酰胺，使用B3LYP（PCM）/ 6-31 + G（D）计算水平的计算已经在分子电子密度理论（MEDT）内分析。这些La催化的分解反应通过涉及两步离子中间体的两步机制进行。使用更酸性的ALCL <sub> 3 </ sub> La有利于动力学和热力学的分解反应。粘接演化理论（BET）分析表明，这些La催化的分解反应从质子转移过程开始，然后在反应第二步骤挤出苯甲酸。 </ p> </ abstract> </span> <span class="z_kbtn z_kbtnclass hoverxs" style="display: none;">展开▼</span> </div> </div> <div class="record"> <h2 class="all_title" id="enpatent33" >著录项</h2> <ul> <li> <span class="lefttit">来源</span> <div style="width: 86%;vertical-align: text-top;display: inline-block;"> <a href='/journal-foreign-35546/'>《Journal of Physical Organic Chemistry》</a> <b style="margin: 0 2px;">|</b><span>2019年第6期</span><b style="margin: 0 2px;">|</b><span>共12页</span> </div> </li> <li> <div class="author"> <span class="lefttit">作者</span> <p id="fAuthorthree" class="threelineshidden zhankaihshouqi"> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=K?cka‐Zych Agnieszka&option=202" target="_blank" rel="nofollow">K?cka‐Zych Agnieszka;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Ríos‐Gutiérrez Mar&option=202" target="_blank" rel="nofollow">Ríos‐Gutiérrez Mar;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Domingo Luis R.&option=202" target="_blank" rel="nofollow">Domingo Luis R.;</a> </p> <span class="z_kbtnclass z_kbtnclassall hoverxs" id="zkzz" style="display: none;">展开▼</span> </div> </li> <li> <div style="display: flex;"> <span class="lefttit">作者单位</span> <div style="position: relative;margin-left: 3px;max-width: 639px;"> <div class="threelineshidden zhankaihshouqi" id="fOrgthree"> <p>Institute of Organic Chemistry and TechnologyCracow University of TechnologyCracow Poland;</p> <p>Departamento de Quimica OrganicaUniversidad de ValenciaBurjassot Spain;</p> <p>Departamento de Quimica OrganicaUniversidad de ValenciaBurjassot Spain;</p> </div> <span class="z_kbtnclass z_kbtnclassall hoverxs" id="zhdw" style="display: none;">展开▼</span> </div> </div> </li> <li > <span class="lefttit">收录信息</span> <span style="width: 86%;vertical-align: text-top;display: inline-block;"></span> </li> <li> <span class="lefttit">原文格式</span> <span>PDF</span> </li> <li> <span class="lefttit">正文语种</span> <span>eng</span> </li> <li> <span class="lefttit">中图分类</span> <span><a href="https://www.zhangqiaokeyan.com/clc/4796.html" title="有机化学一般性问题">有机化学一般性问题;</a></span> </li> <li class="antistop"> <span class="lefttit">关键词</span> <p style="width: 86%;vertical-align: text-top;"> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=aluminum catalyst&option=203" rel="nofollow">aluminum catalyst;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=bonding evolution theory&option=203" rel="nofollow">bonding evolution theory;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=decomposition reaction&option=203" rel="nofollow">decomposition reaction;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=electron localization function&option=203" rel="nofollow">electron localization function;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Lewis acid catalysis&option=203" rel="nofollow">Lewis acid catalysis;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=molecular electron density theory&option=203" rel="nofollow">molecular electron density theory;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=nitroalkenes&option=203" rel="nofollow">nitroalkenes;</a> </p> <div class="translation"> 机译：铝催化剂;粘接演化理论;分解反应;电子定位功能;路易斯酸催化;分子电子密度理论;Nitroallenes; 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2013</span><span>,第005期</span> </span> </div> </li> <li> <div> <b>6. </b><a class="enjiyixqcontent" href="/academic-conference-cn_meeting-41457_thesis/020222476534.html">大气中偏二甲肼和臭氧反应生成亚硝基二甲胺和甲醛机理的理论研究</a> <b>[C]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=黄丹&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 黄丹</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=刘祥萱&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,刘祥萱</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=王煊军&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,王煊军</a> <span> <a href="/conference-cn-41457/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 中国化学会第八届化学推进剂学术会议 </a> <span> <span> . -1</span> </span> </div> </li> <li> <div> <b>7. </b><a class="enjiyixqcontent" href="/academic-degree-domestic_mphd_thesis/020313227030.html">钯催化苯丙氨酸甲酯衍生物的间位烷基化和邻位硝基化反应研究</a> <b>[A] </b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=刘洁玉&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 刘洁玉</a> <span> . 2018</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/06120105179359.html">制备硝基氧基酯、硝基氧基硫酯、硝基氧基碳酸酯和硝基氧基硫代碳酸酯的方法、用于所述方法的中间体及其制备</a> <b>[P]</b> . <span> 中国专利： CN1984871A </span> <span> . 2007-06-20</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/06120110402884.html">对硝基苯氧基白桦脂醇基(28)甲酰酯及以其合成的白桦酯醇衍生物、制备方法及应用</a> <b>[P]</b> . <span> 中国专利： CN107892709A </span> <span> . 2018-04-10</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130407470198.html">Hydrosilane/Lewis acid adduct, particularly aluminum, iron, and zinc, method for preparing same, and use of said same in reactions for reducing carbonyl derivatives</a> <b>[P]</b> . <span> 外国专利：  US10099986B2 </span> <span> . 2018-10-16</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：氢硅烷/路易斯酸加合物，特别是铝，铁和锌，其制备方法及其在还原羰基衍生物的反应中的用途 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130407370990.html">HYDROSILANE/LEWIS ACID ADDUCT, PARTICULARLY ALUMINUM, IRON, AND ZINC, METHOD FOR PREPARING SAME, AND USE OF SAID SAME IN REACTIONS FOR REDUCING CARBONYL DERIVATIVES</a> <b>[P]</b> . <span> 外国专利：  US2018009730A1 </span> <span> . 2018-01-11</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：氢化硅烷/路易斯酸产物，特别是铝，铁和锌，其制备方法，以及相同的胺在减少羰基衍生物的反应中的用途 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130407967136.html">HYDROSILANE/LEWIS ACID ADDUCT, PARTICULARLY ALUMINUM, IRON, AND ZINC, METHOD FOR PREPARING SAME, AND USE OF SAID SAME IN REACTIONS FOR REDUCING CARBONYL DERIVATIVES</a> <b>[P]</b> . <span> 外国专利：  EP3250577A1 </span> <span> . 2017-12-06</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：氢化硅烷/路易斯酸产物，特别是铝，铁和锌，其制备方法，以及相同的胺在减少羰基衍生物的反应中的用途 </span> </p> </li> </ul> </div> </div> </div> <div class="theme cardcommon" style="overflow: auto;display:none"> <h3 class="all_title" id="enpatent55">相关主题</h3> <ul id="subject"> </ul> </div> </div> </div> </div> <div class="right rightcon"> <div class="details_img cardcommon clearfix" style="margin-bottom: 10px;display:none;" > </div> </div> </div> <div id="thesis_get_original1" class="downloadBth" style="bottom: 19px;z-index: 999;" onclick="ywcd('0704025793936','4',7,2,1,'',this,24)" 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