{"id":7477,"date":"2013-08-14T08:05:37","date_gmt":"2013-08-14T12:05:37","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=7477"},"modified":"2026-04-20T05:03:06","modified_gmt":"2026-04-20T10:03:06","slug":"bond-strengths-radical-stability","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2013\/08\/14\/bond-strengths-radical-stability\/","title":{"rendered":"Bond Strengths And Radical Stability"},"content":{"rendered":"<p><strong>Bond Dissociation Energies And Radical Stability<\/strong><\/p>\n<ul>\n<li>The last article discussed factors which stabilize &#8211; and destabilize &#8211; free radials.<\/li>\n<li>So how do we <strong>quantify<\/strong> free-radical stability?<\/li>\n<li>Some caution is required &#8211; <em><span style=\"color: #993366;\">see this<\/span> <a href=\"#noteone\">note<\/a> <\/em>&#8211; but if we keep enough variables constant, the <strong>strength of C\u2013H bonds<\/strong> (&#8220;Bond Dissociation Energies&#8221;, or BDE&#8217;s) are a pretty good guide to the stability of carbon radicals, and other radicals besides.<\/li>\n<\/ul>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-38592\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2024\/11\/0-summary-bond-dissociation-energies-bdes-reflect-radical-stability-trends-primary-secondary-tertiary-methyl.gif\" alt=\"summary-bond dissociation energies bdes reflect radical stability trends primary secondary tertiary methyl\" width=\"640\" height=\"535\" \/><\/a><\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">Quantifying Free Radical Stability<\/a><\/li>\n<li><a href=\"#two\">Why Does H2O Have A Higher Bond Dissociation Energy Than CH4?<\/a><\/li>\n<li><a href=\"#three\">Bond Dissociation Energy Correlates With Free-Radical Stability<\/a><\/li>\n<li><a href=\"#four\">Factor #1: Stability Increases In The Order Methyl &lt; Primary &lt; Secondary &lt; Tertiary. Bond Dissociation Energies (BDE&#8217;s)<\/a><\/li>\n<li><a href=\"#five\">Factor#2: Free Radicals Are Stabilized By Resonance.\u00a0<\/a><\/li>\n<li><a href=\"#six\">Factor #3: Free Radials Are Stabilized By Adjacent Atoms With Lone Pairs<\/a><\/li>\n<li><a href=\"#seven\">Factor #4: Across The Periodic Table, Free-Radical Stability Decreases With Increasing Electronegativity<\/a><\/li>\n<li><a href=\"#eight\">Factor #5: Down The Periodic Table, Free-Radical Stability Increases With Increasing Size Of The Atom<\/a><\/li>\n<li><a href=\"#nine\">Factor #6: The Stability Of The Free Radical Decreases As The Orbital Is Held Closer To The Nucleus<\/a><\/li>\n<li><a href=\"#ten\">Factor #7: Electron Withdrawing Groups Destabilize Free Radicals<\/a><\/li>\n<li><a href=\"#eleven\">Summary: Quantifying Free-Radical Stability With Bond Dissociation Energies (BDE&#8217;s)<\/a><\/li>\n<li><a href=\"#notes\">Notes<\/a><\/li>\n<li><a href=\"#references\">(Advanced) References and Further Reading<\/a><\/li>\n<\/ol>\n<hr \/>\n<h2><a id=\"one\"><\/a>1. Quantifying Free Radical Stability<\/h2>\n<p>In the last article we went through the factors which affect the stability of free radicals<span style=\"color: #993366;\"> <em>(See article &#8211; <a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/2013\/08\/02\/3-factors-that-stabilize-free-radicals\/\">Factors Which Stabilize Free Radicals<\/a>).\u00a0<\/em><\/span><\/p>\n<p>The bottom line is that<\/p>\n<ul>\n<li><strong>Free radicals are electron-deficient<\/strong> due to their half-filled orbital.\u00a0 Therefore, radicals will be stabilized by any factor which either<\/li>\n<li><strong>donates electron density<\/strong> to the half-filled orbital, <strong>or <\/strong><\/li>\n<li><strong>disperses <\/strong>the orbital containing the half filled orbital over a <strong>larger volume<\/strong> (a.k.a &#8220;delocalize&#8221; it) <strong>or <\/strong><\/li>\n<li>results in the half-filled orbital being <strong>further away<\/strong> from the positively-charged nucleus <span style=\"color: #993366;\"><em>(i.e. feeling less effective nuclear charge)<\/em><\/span><\/li>\n<\/ul>\n<p>There were a total of six factors we discussed. You might initially find it hard to keep track of the factors we mentioned. That&#8217;s OK, because interestingly, there is <strong>one measurement\u00a0which can help us keep all of these factors straight.<\/strong><span style=\"color: #993366;\"><em> [EDIT: provided we confine ourselves to some simple examples provided herein]<\/em><\/span><\/p>\n<p>It&#8217;s called <strong><a href=\"http:\/\/en.wikipedia.org\/wiki\/Bond-dissociation_energy\">Bond Dissociation Energy <\/a>[BDE]<\/strong>. You might be familiar with it already!<\/p>\n<p>There&#8217;s probably \u00a0a table of bond dissociation energies in your textbook, usually within the first 100 pages or so.<\/p>\n<p>What many people take some time to realize is that BDE is a measure of the energy required for\u00a0<b>homolytic <\/b>bond cleavage, and as we discussed earlier, homolytic bond cleavage leads to the formation of free radicals [<span style=\"color: #993366;\"><em><strong>heterolytic<\/strong> bond cleavage, which is much more common in organic chemistry, leads to the formation of at least one charged species [ions]]<\/em><\/span>.<\/p>\n<p>Therefore, BDE is essentially a measure of <b>free radical<\/b> <strong>stability<\/strong>, at least for C-H bonds. <span style=\"color: #993366;\"><em>[EDIT: As Prof. Wenthold points out, the stability of the starting molecule is also a factor to consider. In this post we deal the simple cases of bonds to H that are unstrained, but in cases with strained bonds, bonds weakened by significant electron repulsion, or bonds to very electronegative atoms, corrections must be made for these factors in order to ascertain <span style=\"text-decoration: underline;\">quantitative<\/span> free radical stabilities]<\/em><\/span><b><br \/>\n<\/b><\/p>\n<p>So let&#8217;s use some bond dissociation energy data to help connect these concepts.<\/p>\n<h2><a id=\"two\"><\/a>2. Why Does Water Have A Higher Bond Dissociation Energy Than Methane?<\/h2>\n<p>Take two molecules &#8211; methane (CH<span class=\"Apple-style-span\" style=\"font-size: 11px;\">4<\/span>) and water (H<sub>2<\/sub>O). Which bond is stronger, O-H or C-H ?<\/p>\n<p>Thinking back to some of the chemistry we&#8217;ve talked about earlier, such as acid-base reactions, it might be tempting to say that O\u2013H is <strong>weaker<\/strong> than C\u2013H, since we can think of many strong bases which will deprotonate water [pK<sub>a<\/sub> = 14], but very few that will deprotonate alkanes [pK<sub>a<\/sub> = 50].<\/p>\n<p>However when we look at the BDE&#8217;s, we see that HO\u2013H is 118 kcal\/mol and H<sub>3<\/sub>C\u2013H is 104 kcal\/mol. So the C\u2013H bond is weaker? What gives?<\/p>\n<p>If you&#8217;re thinking about BDE&#8217;s and acid-base reactions, you&#8217;re using the wrong mental model.<\/p>\n<p>Acid base reactions involve <b>heterolytic<\/b> cleavage.\u00a0 BDE&#8217;s are a measure of\u00a0<strong>homolytic<\/strong> cleavage.<\/p>\n<p>Instead of the stability of the <strong>ions<\/strong> (<em><span style=\"color: #993366;\">heterolytic cleavage!<\/span>)<\/em> we need to look at the stability of the <strong>free radicals<\/strong> <em>(<span style=\"color: #993366;\">homolytic cleavage<\/span>).<\/em><\/p>\n<p>Here&#8217;s an example of what we need to look at in this case:<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-45743\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2026\/04\/1-homolytic-bond-breaking-h2o-hydroxyl-radical-methane-methyl-radical.gif\" alt=\"homolytic bond breaking h2o hydroxyl radical methane methyl radical\" width=\"640\" height=\"549\" \/><\/a><\/p>\n<p>Note how we&#8217;re forming a H radical in both cases. What&#8217;s different is the identity of the <b>other <\/b>radical.<\/p>\n<p>That leads us to comparing the stability of H<sub>3<\/sub>C\u2022 \u00a0and HO\u2022 \u00a0, and we learned previously that <strong>[all else being equal]\u00a0<\/strong>\u00a0the stability of free radicals <strong>decreases as we go from left to right across the periodic table<\/strong>, since O is more electronegative than C and that partially empty orbital is being held more closely to the positively charged nucleus. \u00a0More on that below.<\/p>\n<h2><a id=\"three\"><\/a>3. Bond Dissociation Energy Is Correlated With Free Radical Stability<\/h2>\n<p>The bottom line for this post is that <strong>bond dissociation energy is correlated to free radical stability. <\/strong><\/p>\n<p>Low bond dissociation energies reflect the formation of stable free radicals, and high bond dissociation energies reflect the formation of unstable free radicals.<\/p>\n<p><span style=\"color: #993366;\"><em>[EDIT: Caveats apply when extending this discussion beyond the scope discussed in this post. See <a href=\"#noteone\">Note 1<\/a>]<\/em><\/span><\/p>\n<p>If we keep one variable constant and vary the other variable, we can analyze the influence of structure on free radical stability.<\/p>\n<p>Here we&#8217;re going to keep\u00a0<strong>H<\/strong> as the variable which is the same, and by examine the trends which influence free radical stability in a new light.<\/p>\n<p>Let&#8217;s look at these seven factors in turn:<\/p>\n<ul>\n<li>Stability increases in the order <strong>methyl<\/strong> <span style=\"color: #993366;\"><em>(least stable)<\/em> <\/span>&lt; primary &lt; secondary &lt; <strong>tertiary<span style=\"color: #993366;\"><em>\u00a0<\/em><\/span><\/strong><span style=\"color: #993366;\"><em>(most stable)<\/em><\/span><\/li>\n<li>Free radicals are stabilized by <strong>resonance<\/strong><\/li>\n<li>Free radicals are stabilized by <strong>adjacent atoms with lone pairs<\/strong><\/li>\n<li>Free radicals increase in stability as the <strong>electronegativity<\/strong> of the atom <strong>decreases<\/strong><\/li>\n<li>Free radicals increase in stability as we go <strong>down<\/strong> the periodic table (larger size, more polarizable)<\/li>\n<li>Free radicals decrease in stability as we go from sp<sup>3<\/sup> to sp<sup>2<\/sup> to sp hybridization<span class=\"Apple-style-span\" style=\"font-size: 11px;\"><br \/>\n<\/span><\/li>\n<li>Adjacent electron withdrawing groups decrease the stability of free radicals.<\/li>\n<\/ul>\n<h2><strong><a id=\"four\"><\/a>4. Factor #1: \u00a0Stability increases in the order methyl &lt; primary &lt; secondary &lt; tertiary<\/strong><\/h2>\n<p>Note that the BDE of C-H bonds decreases as we go from methyl to primary to secondary to tertiary. They are easier to break since homolytic bond cleavage results in a <strong>more stable radical<\/strong>.<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-45747\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2026\/04\/2-radical-stability-increases-in-order-methyl-primary-secondary-tertiary.gif\" alt=\"radical stability increases in order methyl primary secondary tertiary\" width=\"640\" height=\"469\" \/><\/a><\/p>\n<h2><strong><a id=\"five\"><\/a>5. Factor #2: Free radicals are stabilized by resonance.<\/strong><\/h2>\n<p>Note the difference in bond strengths between the (primary) C-H bond of propane and of the alkyl C-H bond of propene. The sizeable difference [~13 kcal\/mol] is a reflection of the greater stability of the resonance-stabilized &#8220;allyl&#8221; radical.<\/p>\n<p>Although not directly comparable, look at the C-H bond strength when it is adjacent to two alkenes \u00a0[76 kcal\/mol]. This &#8220;doubly allylic&#8221; C\u2013H bond is even weaker, reflecting the fact that a <strong>greater number of resonance forms<\/strong> are available for the radical species.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-45750\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2026\/04\/3-free-radicals-stabilized-by-resonance.gif\" alt=\"free radicals stabilized by resonance\" width=\"640\" height=\"529\" \/><\/a><\/p>\n<h2><strong><a id=\"six\"><\/a>6. Factor #3: Free radicals are stabilized by adjacent atoms with lone pairs.<\/strong><\/h2>\n<p>[This is a subtle point!]. Note the difference in bond strengths between the C-H bond of methane [104 kcal\/mol]\u00a0 and that of methanol [95 kcal\/mol]. In between we have the C-H bond of fluoromethane [101 kcal\/mol].<\/p>\n<p>Note that even though fluorine is more electronegative than H, the presence of the lone pairs on F is actually <strong>stabilizing<\/strong> relative to H.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-45754\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2026\/04\/4-free-radicals-stabilized-by-adjacent-lone-pair-donors-such-as-O-and-N.gif\" alt=\"free radicals stabilized by adjacent lone pair donors such as O and N\" width=\"640\" height=\"446\" \/><\/a><\/p>\n<h2><strong><a id=\"seven\"><\/a>7. Factor #4: Across the periodic table, free radical stability decreases with increasing electronegativity.<\/strong><\/h2>\n<p>Note the difference between H-CH<sub>3<\/sub> [104], H-OH [119] and H-F [136].<\/p>\n<p>The most electronegative element has the <strong>least<\/strong> stable free radical and this is reflected in the higher bond strength.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-45758\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2026\/04\/5-radical-stability-decreases-going-left-to-right-along-periodic-table-carbon-most-stable-fluorine-least-stable.gif\" alt=\"radical stability decreases going left to right along periodic table carbon most stable fluorine least stable\" width=\"640\" height=\"445\" \/><\/a><\/p>\n<h2><strong><a id=\"eight\"><\/a>8. Factor #5: Down the periodic table, free radical stability increases with increasing size of the atom.<\/strong><\/h2>\n<p>Look how the BDE decreases as we go from H-F [136] to H-Cl [103] to H-Br [87] to H-I [71]. As we should expect by now, the iodide radical is the most stable, since the orbital is larger in size and is <del>therefore &#8220;spread out&#8221; over a larger volume.<\/del> further away from the nucleus, therefore &#8220;feeling&#8221; less effective nuclear charge than would a smaller atom. <span style=\"color: #993366;\"><em>[thanks to commenter<strong> Xylene<\/strong> for this constructive suggestion].<\/em><\/span><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-45759\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2026\/04\/6-free-radical-stability-increases-going-down-the-periodic-table-iodine-more-than-f.gif\" alt=\"free radical stability increases going down the periodic table iodine more than f\" width=\"640\" height=\"445\" \/><\/a><\/p>\n<h2><strong><a id=\"nine\"><\/a>9. Factor #6: The stability of the free radical decreases as the orbital is held closer to the nucleus.<\/strong><\/h2>\n<p>Look what happens to the bond strength as we go from ethane, which is <em>sp<\/em><sup>3<\/sup> hybridized [98 kcal\/mol] to ethene [<em>sp<\/em><sup>2<\/sup>, 109 kcal\/mol]\u00a0to acetylene [<em>sp<\/em>, 125 kcal\/mol].<\/p>\n<p>This is largely the same effect as #5 above &#8211; the farther away from the nucleus the half-filled orbital is, the more stable it will be.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-45764\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2026\/04\/7-free-radical-stability-decreases-going-from-sp3-to-sp2-to-sp.gif\" alt=\"free radical stability decreases going from sp3 to sp2 to sp\" width=\"640\" height=\"512\" \/><\/a><\/p>\n<h2><strong><a id=\"ten\"><\/a>10. Factor #7: electron withdrawing groups destabilize free radicals.<\/strong><\/h2>\n<p>To isolate this effect it&#8217;s important to look at examples where the electron-withdrawing group cannot donate a lone pair to the radical (see factor #3). One good example is comparing the C-H strength in ethane vs. trifluoroethane.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-45765\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2026\/04\/8-electron-withdrawing-groups-destabiize-free-radicals-eg-cf3.gif\" alt=\"electron withdrawing groups destabiize free radicals eg cf3\" width=\"640\" height=\"479\" \/><\/a><\/p>\n<h2><strong><a id=\"eleven\"><\/a>11. Summary: Quantifying Free Radical Stability With Bond Dissociation Energies<\/strong><\/h2>\n<p>Hopefully it&#8217;s clear by now that where C-H bonds are concerned,\u00a0 <strong>by examining bond dissociation energies, we can discern trends in free-radical stabilities.\u00a0<\/strong><\/p>\n<p>This will be of prime importance in understanding\u00a0<strong>selectivity<\/strong> in free radical reactions: &#8220;which free radical forms?&#8221;.<\/p>\n<p>A subtle point is that it is also important in understanding fragmentation patterns in mass spectroscopy, but we&#8217;re not there yet.<br \/>\n<strong>Next Post: <a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/08\/30\/radical-reactions-why-is-light-or-heat-required\/\">Radical Reactions &#8211; Why Is Heat Or Light Required?<\/a>\u00a0<\/strong><\/p>\n<hr \/>\n<h2><b><a id=\"notes\"><\/a>Notes<\/b><\/h2>\n<div class=\"related-articles\"><p><strong>Related Articles<\/strong><\/p><ul><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/08\/30\/radical-initiation-why-is-light-or-heat-required\/\" class=\"\"><span>Free Radical Initiation: Why Is \u201cLight\u201d Or \u201cHeat\u201d Required?<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/09\/06\/initiation-propagation-termination\/\" class=\"\"><span>Initiation, Propagation, Termination<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/12\/09\/in-summary-free-radicals\/\" class=\"\"><span>In Summary: Free Radicals<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/08\/02\/3-factors-that-stabilize-free-radicals\/\" class=\"\"><span>3 Factors That Stabilize Free Radicals<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/09\/23\/selectivity-in-free-radical-reactions\/\" class=\"\"><span>Selectivity In Free Radical Reactions<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/organic-chemistry-practice-problems\/radicals-practice-quizzes\/\" class=\"\"><span>Free Radicals Practice Quizzes (MOC Membership required)<\/span><\/a><\/li><\/ul><\/div>\n<p><a href=\"https:\/\/labs.chem.ucsb.edu\/zakarian\/armen\/11---bonddissociationenergy.pdf\"><strong>Source<\/strong><\/a> of bond dissociation energies in this article (PDF)<\/p>\n<p><strong><a id=\"noteone\"><\/a>Note 1. <\/strong>More caution is required than I had previously indicated regarding the main thesis of this post &#8211; that free radical stabilities are solely reflected by bond strengths. They depend on the stability of <span style=\"text-decoration: underline;\">both<\/span> reactant and reagent.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14555\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/9-bond-strengths-are-relative-energies-of-radicals-and-reactant-and-depend-on-stabilities-of-both.png\" alt=\"bond-strengths-are-relative-energies-of-radicals-and-reactant-and-depend-on-stabilities-of-both\" width=\"450\" height=\"224\" srcset=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/9-bond-strengths-are-relative-energies-of-radicals-and-reactant-and-depend-on-stabilities-of-both.png 476w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/9-bond-strengths-are-relative-energies-of-radicals-and-reactant-and-depend-on-stabilities-of-both-300x149.png 300w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/9-bond-strengths-are-relative-energies-of-radicals-and-reactant-and-depend-on-stabilities-of-both-320x159.png 320w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/9-bond-strengths-are-relative-energies-of-radicals-and-reactant-and-depend-on-stabilities-of-both-360x179.png 360w\" sizes=\"(max-width: 450px) 100vw, 450px\" \/><\/p>\n<p>Edits are indicated inline. For more discussion see bottom section.[ <span style=\"color: #993366;\"><em>TL;DR &#8211; the general <span style=\"text-decoration: underline;\">trends<\/span> in this post are valid because we discuss bonds to H, but use caution when comparing any other type of bond other than hydrogen.<\/em><\/span>] Thanks to Prof. Paul Wenthold (Purdue University) for his input.<\/p>\n<p>Using the bond strengths (BDE&#8217;s) of <em>unstrained<\/em> bonds to <span style=\"text-decoration: underline;\">hydrogen<\/span> is a <a href=\"http:\/\/pubs.acs.org\/doi\/abs\/10.1021\/jo101661c?journalCode=joceah\">reasonable method<\/a> for discerning trends in radical stabilities, as discussed in this post.<\/p>\n<p>However, BDE&#8217;s\u00a0<em>in and of themselves<\/em> are not reliable for discerning <span style=\"text-decoration: underline;\">absolute<\/span>\u00a0radical stabilities in cases where the bond may be weakened by strain, repulsion between lone pairs, or other factors.<br \/>\nFor example the BDE for hydrogen peroxide is 51 kcal\/mol, which does <i>NOT\u00a0<\/i>imply that the HO\u2022 radical is stable, but rather that the O\u2013O bond is <strong>destabilized<\/strong> by repulsion between the lone pairs.<\/p>\n<p><strong><a id=\"notetwo\"><\/a>Note 2. <\/strong><strong>\u00a0<\/strong>In looking at bond strength data there are often differences in 2-3 kcal between different sources. The important part here is not so much the absolute numbers, but the <strong>trends<\/strong>. These two files helped when compiling the numbers for this post:<\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2013\/08\/Bond-Dissociation-Energies.pdf\">Bond Dissociation Energies<\/a><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2013\/08\/C-H-bond-strengths.pdf\">C-H bond strengths<\/a><\/p>\n<hr \/>\n<h2><a id=\"references\"><\/a>(Advanced) References and Further Reading:<\/h2>\n<ol>\n<li><strong>Shortcomings of Basing Radical Stabilization Energies on Bond Dissociation Energies of Alkyl Groups to Hydrogen<br \/>\n<\/strong>Andreas A. Zavitsas, Donald W. Rogers, and Nikita Matsunaga<strong><br \/>\n<\/strong><em>The Journal of Organic Chemistry<\/em><strong> 2010, <\/strong><em>75<\/em> (16), 5697-5700<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/jo101127m\">1021\/jo101127m<\/a><br \/>\nSeveral textbooks, including some advanced ones, provide radical stabilization energies, and this paper discusses why that may not be the best way to quantify the stability of free radicals.<\/li>\n<li><strong>On the Advantages of Hydrocarbon Radical Stabilization Energies Based on R\u2212H Bond Dissociation Energies<br \/>\n<\/strong>Matthew D. Wodrich, W. Chad McKee, and Paul von Ragu\u00e9 Schleyer<strong><br \/>\n<\/strong><em>The Journal of Organic Chemistry<\/em><strong> 2011, <\/strong><em>76<\/em> (8), 2439-2447<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/jo101661c\">1021\/jo101661c<\/a><br \/>\nThis paper addresses some of the shortcomings with the approach used in Ref #1 above. The late Prof. Schleyer was a very influential figure in organic chemistry, and was a pioneer in using computational methods to address interesting problems in organic chemistry.<\/li>\n<li><strong>The Radical Stabilization Energy of a Substituted Carbon-Centered Free Radical Depends on Both the Functionality of the Substituent and the Ordinality of the Radical<br \/>\n<\/strong>Marvin L. Poutsma<strong><br \/>\n<\/strong><em>The Journal of Organic Chemistry<\/em><strong> 2011, <\/strong><em>76<\/em> (1), 270-276<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/jo102097n\">1021\/jo102097n<\/a><\/li>\n<li><strong>A Single Universal Scale of Radical Stabilization Energies Does Not Exist: Global Bond Dissociation Energies and Radical Thermochemistries Are Described by Combining Two Universal Scales<br \/>\n<\/strong>Andreas A. Zavitsas<strong><br \/>\n<\/strong><em>The Journal of Organic Chemistry<\/em><strong> 2008<\/strong>, <em>73<\/em> (22), 9022-9026<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/jo8018768\">1021\/jo8018768<\/a><\/li>\n<li><strong>Bond Dissociation Energies by Kinetic Methods<br \/>\n<\/strong> A. Kerr<br \/>\n<em>Chemical Reviews<\/em> <strong>1966,<\/strong> <em>66<\/em> (5), 465-500<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/cr60243a001\">10.1021\/cr60243a001<\/a><br \/>\nThis paper describes experimental techniques for measuring homolytic BDEs.<\/li>\n<li><strong>III &#8211; Bond energies<\/strong><br \/>\nSidney W. Benson<br \/>\n<em>Journal of Chemical Education<\/em> <strong>1965,<\/strong> <em>42<\/em> (9), 502<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/ed042p502\">10.1021\/ed042p502<\/a><br \/>\nThis paper describes the empirical measurement of homolytic bond dissociation energies. This paper was written by Prof. Benson while at the Stanford Research Institute (now SRI International), a non-profit research center very close to Stanford University. In 1978, Prof. Benson joined Prof. George Olah at USC and helped established the Loker Hydrocarbon Research Institute there.<\/li>\n<li><strong>From equilibrium acidities to radical stabilization energies<\/strong><br \/>\nFrederick G. Bordwell and Xian Man Zhang<br \/>\n<em>Accounts of Chemical Research<\/em> <strong>1993,<\/strong> <em>26<\/em> (9), 510-517<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ar00033a009\">10.1021\/ar00033a009<\/a><br \/>\nThis paper attempts to correlate the acidity of a proton with the BDE of the corresponding C-H or X-H bond.<\/li>\n<li><strong>Ab Initio Calculations of the Relative Resonance Stabilization Energies of Allyl and Benzyl Radicals<br \/>\n<\/strong>David A. Hrovat and Weston Thatcher Borden<strong><br \/>\n<\/strong><em>The Journal of Physical Chemistry<\/em><strong> 1994, <\/strong><em>98<\/em> (41), 10460-10464<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/j100092a014\">1021\/j100092a014<\/a><br \/>\nThe stabilization energy of a vinyl group (in the allyl radical) and a phenyl group (in the benzyl radical) has been calculated to be 15.7 kcal\/mol and 12.5 kcal\/mol, respectively.<\/li>\n<li><strong>Effects of adjacent acceptors and donors on the stabilities of carbon-centered radicals<br \/>\n<\/strong> G. Bordwell, Xianman Zhang, and Mikhail S. Alnajjar<strong><br \/>\n<\/strong><em>Journal of the American Chemical Society<\/em><strong> 1992<\/strong>, <em>114<\/em> (20), 7623-7629<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja00046a003\">10.1021\/ja00046a003<\/a><br \/>\nTable I in this paper contains stabilization energies of methyl radicals with various substituents (e.g. \u00b7CH<sub>2<\/sub>X).<\/li>\n<\/ol>\n","protected":false},"excerpt":{"rendered":"<p>Bond Dissociation Energies And Radical Stability The last article discussed factors which stabilize &#8211; and destabilize &#8211; free radials. So how do we quantify free-radical <\/p>\n","protected":false},"author":1,"featured_media":38592,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1411],"tags":[182,608,464,607,606],"post_folder":[],"class_list":["post-7477","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-free-radical-reactions","tag-bond-strengths","tag-primary","tag-radical-stability","tag-secondary","tag-tertiary"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Bond Strengths And Radical Stability &#8211; Master Organic Chemistry<\/title>\n<meta name=\"description\" content=\"Bond dissociation energies (BDE&#039;s) are a useful guide to free-radical stabilities. 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