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C―H···O hydrogen bonding interactions for sterically hindered phenols and their phenoxyl radicals

机译：C-H··O氢键合相互作用的空间阻碍酚及其苯氧基自由基

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Abstract > Sterically hindered phenols have been widely used as chain‐breaking antioxidants in chemical and polymeric industries, and the remarkable stabilities of their phenoxyl radicals are generally attributed to the steric effects and resonance stabilization of the unpaired electron into the aromatic ring. Non‐covalent interaction (NCI) analysis shows that there are four intramolecular C―H···O hydrogen bonds between oxygen atom and the ortho t ‐butyl C―H bonds for the sterically hindered phenoxyl radicals and their phenolic precursors. The C―H···O hydrogen bonds can be directly visualized and quantified from the reduced density gradient NCI isosurfaces and atoms‐in‐molecules analysis, respectively. Furthermore, the phenolic O―H bond strength decreases gradually with increasing volume of the ortho alkyl substituents in three different phenol model systems (Table?5). The nice linear correlation of the O―H bond dissociation enthalpies with the Taft's steric parameters (Figure?8) provides additional evidences to support formation of the intramolecular C―H···O hydrogen bonds between oxygen atom and the ortho t ‐alkyl C―H bonds. </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> >在化学和聚合物行业中被广泛用作链断破碎的抗氧化剂，并且它们的苯氧基自由基的显着稳定性通常归因于未配对的电子进入芳环的空间效应和共振稳定。非共价相互作用（NCI）分析表明，氧原子与氧原子和官能邻苯甲酰基的氧原子和邻核苯二酯之间有四个分子内C-H··氢键。它们的酚醛前体。 C-H···O氢键可以分别直接可视化和量化密度梯度NCI异螺段和原子分子分析。此外，酚类O-H键合强度随着三种不同酚模型系统中的烷基取代基的增加而逐渐降低（表→5）。 O-H粘合解离焓与塔夫脱的空间参数（图3）的良好线性相关性提供了额外的证据，以支持形成氧原子和γortho t之间的分子内C-H···氢键的形成</ i>-烷基C-H键。 </ 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5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=Wang Jinhu&option=202" target="_blank" rel="nofollow">Wang Jinhu;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Liu Chunli&option=202" target="_blank" rel="nofollow">Liu Chunli;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Liu Xuejing&option=202" target="_blank" rel="nofollow">Liu Xuejing;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Shao Linjun&option=202" target="_blank" rel="nofollow">Shao Linjun;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Zhang Xian‐Man&option=202" target="_blank" rel="nofollow">Zhang Xian‐Man;</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>College of Chemistry Chemical Engineering and Material ScienceZaozhuang UniversityZaozhuang Shandong China;</p> <p>College of Chemistry Chemical Engineering and Material ScienceZaozhuang UniversityZaozhuang Shandong China;</p> <p>College of Chemistry Chemical Engineering and Material ScienceZaozhuang UniversityZaozhuang Shandong China;</p> <p>Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals ProcessShaoxing UniversityZhejiang China;</p> <p>College of Chemistry Chemical Engineering and Material ScienceZaozhuang UniversityZaozhuang Shandong China;</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=atoms‐in‐molecules (AIM)&option=203" rel="nofollow">atoms‐in‐molecules (AIM);</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=non‐covalent interaction (NCI)&option=203" rel="nofollow">non‐covalent interaction (NCI);</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=sterically hindered phenols/phenoxyls&option=203" rel="nofollow">sterically hindered phenols/phenoxyls;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=hydrogen bonding interactions&option=203" rel="nofollow">hydrogen bonding interactions;</a> </p> <div class="translation"> 机译：原子分子（AIM）;非共价相互作用（NCI）;空间受阻酚/苯氧基;氢键相互作用; 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<a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=祝黔江&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,祝黔江</a> <span> <a href="/journal-cn-15070/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 无机化学学报 </a> </span> <span> . 2002</span><span>,第005期</span> </span> </div> </li> <li> <div> <b>6. </b><a class="enjiyixqcontent" href="/academic-conference-cn_meeting-6185_thesis/020221623804.html">碳酸氢钠溶液中钴离子活化氧气氧化氨基酚产生羟基自由基的研究</a> <b>[C]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=施薇&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 施薇</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=徐爱华&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,徐爱华</a> <span> <a href="/conference-cn-6185/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 第七届全国环境化学学术大会 </a> <span> <span> . 2013</span> </span> </div> </li> <li> <div> <b>7. </b><a class="enjiyixqcontent" href="/academic-degree-domestic_mphd_thesis/020312756803.html">卤代甲基自由基、卤代烷和氢氟醚类化合物与一些自由基反应机理及动力学性质的理论研究</a> <b>[A] </b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=贾秀娟&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 贾秀娟</a> <span> . 2010</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/0612065227.html">β,β-二羟基中位取代的二氢卟酚、异细菌二氢卟酚、细菌二氢卟酚,和从β,β-未取代的四吡咯大环制备所述化合物的方法</a> <b>[P]</b> . <span> 中国专利： CN1043143C </span> <span> . 1999.04.28</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/06120104365066.html">β,β'-二羟基中位取代的二氢卟酚、异细菌二氢卟酚、细菌二氢卟酚,和从β,β'-未取代的四吡咯大环制备所述化合物的方法</a> <b>[P]</b> . <span> 中国专利： CN1161697A </span> <span> . 1997-10-08</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130456976542.html">A sterically hindered phenolic-containing foamable styrene polymer bead and a process for producing the same (PERAL-SHAPED, EXPANDABLE STYRENE POLYMERS CONTAINING STERICALLY INHIBITED PHENOLS)</a> <b>[P]</b> . <span> 外国专利：  KR960704968A </span> <span> . 1996-10-09</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：位阻含酚的可发泡苯乙烯聚合物珠粒及其制备方法（含位阻酚的全形，可膨胀苯乙烯聚合物） </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130478575389.html">Sterically hindered hexa:hydrocarbyl-di:stannane derivs. - decomposing cleanly to stannyl radicals on heating, useful as radical initiators, e.g. for olefin polymerisation</a> <b>[P]</b> . <span> 外国专利：  DE2830244A1 </span> <span> . 1980-01-31</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：立体受阻的六：烃基-二：锡烷衍生物。 -加热时可干净地分解成苯乙烯基，可用作自由基引发剂，例如用于烯烃聚合 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130452606214.html">A synergistic mixture of a 2,4-dimethyl-6-s-alkyl phenol and a sterically hindered phenol.</a> <b>[P]</b> . <span> 外国专利：  NL1005137C2 </span> <span> . 1999-02-02</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：2，4-二甲基-6-s-烷基苯酚和位阻酚的协同混合物。 </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;" 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