Effects of Charge, Size, and Shape of Transition States, Bound Intermediates, and Confining Voids in Reactions of Alkenes on Solid Acids

Sarazen Michele L.; Iglesia Enrique

摘要

Abstract > Solid acids with sites varying in acid strength and in confining environments are used here to examine, through kinetic experiments and theory, how size and shape of organic guests and inorganic hosts at ion‐pair transition states (TS) influence reactivity. Reactions of C <sub>2</sub> ?C <sub>4</sub> alkene mixtures serve as the illustrative example; they involve kinetically‐relevant C?C coupling between alkenes and bound alkoxides that saturate the surface on microporous (TON) and mesoporous (SiAl) aluminosilicates of similar acid strength and on stronger heteropolytungstic acids (HPW). Rate constants (per H + ) increase with increasing TS size (number of C‐atoms) because of the combined effects of size/substitution on proton affinities of coupling products and on van der Waals (vdW) contacts between carbocations and voids. When the voids and organic moieties are similar in dimension, these contacts require framework distortions, leading to dispersive interactions that are compensated in part by enthalpic penalties associated with the distortions, which are quantified here with DFT‐derived atomic displacements and distortion energies. DFT‐derived proton affinities of the coupling products and vdW interaction energies between the TS and voids represent the most accurate and complete descriptors of reactivity, as the size and shape of TS structures vary in C?C coupling steps and more generally in acid‐catalyzed transformations, and can be used in designing voids for stabilizing specific host‐guest pairs. </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> > 这里使用具有在酸强度和限制环境中不同的位点的固体酸进行检查，通过动力学实验和理论，有机客人和无机宿主在离子对转换状态（TS）影响反应性的情况下的尺寸和形状。 C.的反应 <sub> 2 </ sub> ？C <sub> 4 </ sub> 烯烃混合物作为说明性实例;它们涉及在烯烃和结合醇盐之间的动力学相关的C-C偶联，其饱和在微孔（吨）和中孔（Sial）硅氧化物上饱和相似酸强度和更强的杂多钨酸（HPW）。速率常数（每H + </ sup> 由于尺寸/取代对偶联产品的质子亲和力和携带空隙之间的范德华（VDW）触点的尺寸/取代的综合效果增加，随着TS尺寸的增加（C-原子数）增加。当空隙和有机部分在尺寸中相似时，这些触点需要框架失真，导致分散相互作用，其部分地通过与扭曲相关的焓惩罚，其在这里用DFT导出的原子位移和变形能量来定量。耦合产品的DFT衍生的质子亲和力和TS和空隙之间的VDW相互作用能量代表反应性最准确和完整的描述符，因为TS结构的尺寸和形状在C？C耦合步骤中变化，更通常在酸催化中转换，并且可用于设计空隙以稳定特定的主机对成对。 </ p> </摘要> </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-16041/'>《ChemCatChem》</a> <b style="margin: 0 2px;">|</b><span>2018年第18期</span><b style="margin: 0 2px;">|</b><span>共10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=Sarazen Michele L.&option=202" target="_blank" rel="nofollow">Sarazen Michele L.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Iglesia Enrique&option=202" target="_blank" rel="nofollow">Iglesia Enrique;</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 Chemical and Biomolecular EngineeringUniversity of California BerkeleyBerkeley CA 94720 USA;</p> <p>Department of Chemical and Biomolecular EngineeringUniversity of California BerkeleyBerkeley CA 94720 USA;</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/1186.html" title="物理化学（理论化学）、化学物理学">物理化学（理论化学）、化学物理学;</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=zeolites&option=203" rel="nofollow">zeolites;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=alkene dimerization&option=203" rel="nofollow">alkene dimerization;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=density functional theory&option=203" rel="nofollow">density functional theory;</a> </p> <div class="translation"> 机译：沸石;烯烃二聚化;密度函数理论; 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href="/patent-detail/061202639377.html">圆筒形状物的尺寸检查装置及圆筒形状物的尺寸检查方法</a> <b>[P]</b> . <span> 中国专利： CN104075672B </span> <span> . 2017.11.07</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/061201896091.html">具有与至少一个相邻参考图像分区的几何形状或尺寸不同的几何形状或尺寸的当前图像分区的移动向量的预测以及使用一个这种预测的编码和解码</a> <b>[P]</b> . <span> 中国专利： CN102498718B </span> <span> . 2016.01.20</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130427090243.html">METHOD FOR PREPARING A TEREPHTHALIC ACID, WHICH CONVERTS A REACTION INTERMEDIATE TO TEREPHTHALIC ACID WHEN THE SOLID CRUDE TEREPHTHALIC ACID OBTAINED AFTER LIQUID-SOLID SEPARATION HAS A PLURALITY OF INTERMEDIATES</a> <b>[P]</b> . <span> 外国专利：  KR20100003674A </span> <span> . 2010-01-11</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：固液分离后获得的固体粗对苯二酸有多个中间体时，可将中间体转化为对苯二酸的对苯二甲酸的制备方法 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130498754147.html">methods for further purification of reaction products, which are due to the effects of concentrated sulphuric acid or steaming on sulfidisch bound sulfur mineral oils are created, dunkelfärbenden, org</a> <b>[P]</b> . <span> 外国专利：  AT11349B </span> <span> . 1903-03-26</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：建立了用于进一步纯化反应产物的方法，这些方法是由于浓硫酸或蒸汽对与硫键合的硫磺矿物油的汽化作用而产生的，邓肯谢尔本登，组织 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130449098622.html">Processes for the synthesis of an arile or alkene borate, for covalent coupling of organic compounds and for the preparation of bornic acids of arile or alkene, functional polymeric solid, arile or alkene borate, and, monoidroborane di-substituted.</a> <b>[P]</b> . <span> 外国专利：  BR9915133A </span> <span> . 2001-08-07</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：合成芳烃或硼酸酯的方法，用于有机化合物的共价偶联，以及制备芳烃或烯烃的硼酸，官能聚合物固体，芳烃或烯烃的硼酸酯以及单取代的单硼烷的方法。 </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('0704022057372','4',7,2,1,'',this,24)" class="delivery" prompt="010401" title="通过人工服务将文献原文发送至邮箱" >获取原文</div> <div class="journalsub-pop-up" style="display: none"> <div class="journal-sub"> 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