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Insights into unusual stability of 5‐membered‐ring endocyclic benzyl carbocations in aqueous solution

机译：在水溶液中的5元环环环苄基碳酸碳钙的不寻常稳定性

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Abstract > The acyclic o ‐oxygen benzyl carbocation 1 , the 6‐membered‐ring endocyclic o ‐oxygen benzyl carbocation 2 , and the 5‐membered‐ring endocyclic o ‐oxygen benzyl carbocation 3 were used as model compounds to get insights into the general phenomenon for the unusual stability of the 5‐membered‐ring endocyclic benzyl carbocations in aqueous solution. The hydride‐ion affinities of 1 , 2 , and 3 in gas phase, acetonitrile, and DMSO were calculated and compared by the density functional theory method, and 3 isodesmic reactions were designed to confirm their thermodynamic stability. What we found is that the 5‐membered‐ring endocyclic o ‐oxygen stabilizes the benzyl carbocation 3 less than the acyclic o ‐oxygen stabilizes the benzyl carbocation 1 in gas phase because of ring strain and through‐bond induction. However, the high solvation energies of the 5‐membered‐ring endocyclic o ‐oxygen benzyl carbocation 3 not only offset the destabilizing effects of ring strain and through‐bond induction but also make it even more stable than the acyclic o ‐oxygen benzyl carbocation 1 in polar solvents like acetonitrile, DMSO, and water. </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”>抽象</ title> > acclic o </ i> - x / i> -oxygen苄基carbocation 1 < / b>，6-元环环环 o o </ i> - 氧杂环苄基碳统计彼此和5-元环环环 -Oxygen用作模型化合物的苄基碳粉型 3，以获得洞察普通现象，以实现水溶液中的5-元环环环苄基碳酸碳酸的不寻常稳定性。通过密度函数理论计算和在气相中，乙腈和DMSO中的氢化物离子亲和性，乙腈和DMSO中的<B> 3 / B>。方法，设计3个体系反应，以确认其热力学稳定性。我们发现的是，5-元环环环 O </ i> - 氧化苄基碳锁定型苄基碳锁定率小于非环循环 o℃-Oxygen稳定由于环菌株和通键诱导，气相中的苄基碳匹配 1 </ b>。然而，5元环环环的高溶剂能量 -OXYGEN苄基碳匹配 3 </ b>不仅抵消了环菌和粘合诱导的稳定效果，还使其比乙腈，DMSO和水的极性溶剂中的无环苄基苄基碳统计彼得苄基碳统一率更稳定。 </ 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>2018年第10期</span><b style="margin: 0 2px;">|</b><span>共5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=Sung Robert&option=202" target="_blank" rel="nofollow">Sung Robert;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Sung Kuangsen&option=202" target="_blank" rel="nofollow">Sung Kuangsen;</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>Department of ChemistryNational Cheng Kung UniversityTainan Taiwan;</p> <p>Department of ChemistryNational Cheng Kung UniversityTainan Taiwan;</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=benzyl carbocation&option=203" rel="nofollow">benzyl carbocation;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=hydride‐ion affinity&option=203" rel="nofollow">hydride‐ion affinity;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=solvation energy&option=203" rel="nofollow">solvation energy;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=stability&option=203" rel="nofollow">stability;</a> </p> <div class="translation"> 机译：苄基碳结区位;氢化物离子亲和力;溶剂化能量;稳定性; 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