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首页> 外文期刊>Journal of Physical Organic Chemistry >[3 + 2] cycloaddition reaction of N,N′N,N′ cyclic azomethine imines toward highly electron‐deficient nitroalkenes: A molecular electron density theory study
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[3 + 2] cycloaddition reaction of N,N′N,N′ cyclic azomethine imines toward highly electron‐deficient nitroalkenes: A molecular electron density theory study

机译：[3 + 2]循环加油反应 n，n' n，n'环偶氮酰亚胺朝向高电子缺陷的Nitroalkenes：分子电子密度理论研究

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Abstract > A molecular electron density theory (MEDT) study at the M06‐2X/6‐31G(d,p) computational level was performed over [3?+?2] cycloaddition (32CA) reaction of azomethine imine 2 ( AI‐2 ) toward highly electron‐deficient trans ‐β‐nitrostyrene 3 ( NS‐3 ) in dimethyl sulfoxide at 110°C. While this reaction can take place through two N3‐C4 and N3‐C5 regioselective reaction channels, in excellent agreement with the experimental outcomes, the calculated rate constants reveal that the N3‐C4 regioselective reaction channel leading to [3?+?2] cycloadduct CA‐1n in a high endo stereoselective fashion is entirely preferred over the N3‐C5 one. Analysis of the electrophilic and nucleophilic Parr functions computed at the reactive sites of separate reagents allows to explain N3‐C4 regioselectivity, while the endo stereoselectivity can be rationalized through non‐covalent interaction analysis in the competitive transition state structures. The electron localization function analysis performed along the stepwise formation of CA‐1n permits to figure out the molecular mechanism of zwitterionic type ( zw ‐type) 32CA reaction between AI‐2 and NS‐3 . Indeed, within the N3 nucleophilic attack of AI‐2 at the electrophilically activated C4 atom of NS‐3 , the first N3‐C4 single bond at intermediate IN‐1n is formed through donation of part of non‐bonding electron density of the N3 nitrogen atom in AI moiety to the C4 carbon atom of NS moiety. In the subsequent step, the formation o </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”>抽象</标题> > M06-2x / 6-31g的分子电子密度理论（MEDT）研究（ D，P）在氮杂甲酰胺酰亚胺（32Ca）对高电子缺陷的[3 + + 2]环加成（32Ca）反应上进行计算水平（32Ca）（ ai-2 / b>）的反应。在110℃的二甲基亚砜中，在二甲基亚砜中，在110℃下，将I>在亚甲基砜中的逆砜（ Ns-3）反式。虽然该反应可以通过两个N3-C4和N3-C5区域选择性反应通道进行，但是与实验结果的优异一致性，计算的速率常数表明，N3-C4区域选择性反应通道导致[3？+ 2]环绕声<B> Ca-1N </ b>在高度 endo </ i>立体选择性时装完全优选N3-C5一体。在单独的试剂的反应部位计算的亲电子和亲核的PARR功能允许解释N3-C4区域选择性，而通过竞争过渡状态结构中的非共价相互作用分析，可以合理地利用“enchOno”区域选择性。 。沿逐步进行的电子定位功能分析</ i>允许的允许释放两性离子型的分子机制（<​​i> zw </ i>型） 32Ca在 Ai-2 / b>和 ns-3之间的反应。实际上，在γ-2的N3亲核侵袭内，在 ns-3 / b>的电泳活化的C4原子下，中间体的第一N3-C4单键键通过将N 3氮原子的非粘合电子密度的部分捐赠给NS部分的C4碳原子，通过捐赠1N </ b>形成。在随后的步骤中，形成o </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5期</span><b style="margin: 0 2px;">|</b><span>共13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=Babazadeh Sayyed Mohsen&option=202" target="_blank" rel="nofollow">Babazadeh Sayyed Mohsen;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Emamian Saeedreza&option=202" target="_blank" rel="nofollow">Emamian Saeedreza;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Zahedi Ehsan&option=202" target="_blank" rel="nofollow">Zahedi Ehsan;</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>Chemistry Department Shahrood BranchIslamic Azad UniversityShahrood Iran;</p> <p>Chemistry Department Shahrood BranchIslamic Azad UniversityShahrood Iran;</p> <p>Chemistry Department Shahrood BranchIslamic Azad UniversityShahrood Iran;</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=32CA reactions&option=203" rel="nofollow">32CA reactions;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=azomethine imines&option=203" rel="nofollow">azomethine imines;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=ELF analysis&option=203" rel="nofollow">ELF analysis;</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 (MEDT) study&option=203" rel="nofollow">molecular electron density theory (MEDT) study;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=NCI analysis&option=203" rel="nofollow">NCI analysis;</a> </p> <div class="translation"> 机译：32CA反应;氮杂甲酸胺酰亚胺;ELF分析;分子电子密度理论（MEDT）研究;NCI分析; 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class="tuijian_authcolor"> . 东北师大学报：自然科学版 </a> </span> <span> . 2007</span><span>,第1期</span> </span> </div> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/academic-journal-cn_chemical-journal-chinese-universities_thesis/0201231568206.html">开环茂金属成环及氢分子消除反应机理的理论研究</a> <b>[J]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=刘楠楠&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 刘楠楠</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=丁益宏&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,丁益宏</a> <span> <a href="/journal-cn-10958/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 高等学校化学学报 </a> </span> <span> . 2012</span><span>,第010期</span> </span> </div> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/academic-journal-cn_acta-chimica-sinica_thesis/0201272165040.html">系列杂氮钛三环中的分子内弱相互作用的紫外光电子能谱和理论研究</a> <b>[J]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=孙政&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 孙政</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=郑世钧&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,郑世钧</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=孟令鹏&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,孟令鹏</a> <span> <a href="/journal-cn-53859/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 化学学报 </a> </span> <span> . 2001</span><span>,第012期</span> </span> </div> </li> <li> <div> <b>6. </b><a class="enjiyixqcontent" href="/academic-conference-cn_meeting-35230_thesis/020221260073.html">一些噻唑杂环偶氮染料分子结构与其电子吸收光谱之间的关系</a> <b>[C]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=刘燕刚&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 刘燕刚</a> <span> <a href="/conference-cn-35230/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 第七届全国物理有机化学讨论会 </a> <span> <span> . 1995</span> </span> </div> </li> <li> <div> <b>7. </b><a class="enjiyixqcontent" href="/academic-degree-domestic_mphd_thesis/020312016933.html">路易斯碱催化的分子内醛–酮交叉Benzoin和偶氮甲碱亚胺[3+3]环化反应的理论研究</a> <b>[A] </b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=张玮&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 张玮</a> <span> . 2018</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/061203760806.html">一种侧链含高电子迁移率芳杂环的醇/水溶性有机小分子阴极界面材料</a> <b>[P]</b> . <span> 中国专利： CN108947927B </span> <span> . 2020.05.26</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/06120111425148.html">一种侧链含高电子迁移率芳杂环的醇/水溶性有机小分子阴极界面材料</a> <b>[P]</b> . <span> 中国专利： CN108947927A </span> <span> . 2018-12-07</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130422508794.html">METHOD OF DETECTING ADVERSE REACTION TO DRUG BASED ON RETROSPECTIVE COHORT STUDY USING ELECTRONIC MEDICAL RECORD, METHOD OF DETECTING ADVERSE REACTION TO INTERVENTION, AND METHOD OF DETECTING ADVERSE REACTION TO DRUG OR INTERVENTION BASED ON RETROSPECTIVE COHORT STUDY USING ELECTRONIC MEDICAL RECORD AND ELECTROCARDIOGRAM DATA</a> <b>[P]</b> . <span> 外国专利： <!-- 世界知识产权组织专利： --> WO2012023681A1 </span> <span> . 2012-02-23</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：基于电子医疗记录的回顾性队列研究来确定药物不良反应的方法，基于电子数据记录的回顾性队列研究来检测药物不良反应或干预的方法以及基于药物的回顾性队列研究检测药物或药物的不良反应的方法 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130425635839.html">Imines and methods of preparing electron deficient olefins using such novel imines</a> <b>[P]</b> . <span> 外国专利： <!-- 美国专利： --> US8053589B1 </span> <span> . 2011-11-08</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：亚胺和使用这种新型亚胺制备缺电子烯烃的方法 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130430379802.html">ELECTRON-INTERFERENCE METHOD OF DETECTING LOCATION AND TYPES OF MOLECULAR GROUPS ON SURFACES OF SMALL BIO OBJECTS INCLUDING NUCLEOTIDE SEQUENCES AND DEVICE THEREFOR(57) The invention relates to detecting a bio-objects structure, it can be used in studying surface structure of small bio-objects such as macromolecules and detecting a location and a type of molecular groups disposed thereon. A device comprises a base with a substrate made from a non-conductive material thereon, a photocathode and an anode, wherein there is a site therebetween for an object to be studied and electron scatterers. There is at least one window inside the photocathode, the photocathode areas bordering the window made from a material with a reduced work function. The window is connected to a region beyond the photocathode by at least one slit, its length exceeds its width. A cooling electrode is arranged at a small depth under the window and the slit region, wherein an accelerating electrode is arranged the ph</a> <b>[P]</b> . <span> 外国专利： <!-- --> EA012215B1 </span> <span> . 2009-08-28</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：检测包括核苷酸序列和装置在内的小生物物体表面上分子组的位置和类型的电子干扰方法（57）本发明涉及检测生物物体的结构，可用于研究小型生物物体的表面结构物体（例如大分子）并检测其上放置的分子的位置和类型。一种装置，包括具有在其上的由非导电材料制成的基底的基底，光电阴极和阳极，其中在其之间存在用于研究对象的位置和电子散射体。光电阴极内至少有一个窗口，该光电阴极区域与窗口相邻，该窗口由功函数降低的材料制成。窗口通过至少一个狭缝连接到光电阴极之外的区域，其长度超过其宽度。在窗口和狭缝区域下方以较小的深度布置有冷却电极，其中在电极和缝隙区域下方布置有加速电极。 </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: 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