{"id":3577,"date":"2011-12-13T12:00:39","date_gmt":"2011-12-13T12:00:39","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=3577"},"modified":"2026-01-16T14:35:36","modified_gmt":"2026-01-16T20:35:36","slug":"resonance-structure-negative-charge-least-basic-atom","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2011\/12\/13\/resonance-structure-negative-charge-least-basic-atom\/","title":{"rendered":"Resonance Structures: Negative Charges Are Best Placed On The Least Basic Atom"},"content":{"rendered":"<p><strong>Evaluating Resonance Structures With Negative Charges: Some Key Principles<\/strong><\/p>\n<p>So far in discussing resonance forms we&#8217;ve mentioned three important principles that govern which resonance form will be most important.<\/p>\n<ul>\n<li>First is the <a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/12\/08\/evaluating-resonance-forms-1-the-rule-of-least-charges\/\">minimization of total charge<\/a>: the resonance form with the fewest charges will be the most important<span style=\"color: #993366;\"><strong><em>\u00a0<\/em><\/strong><em>(which is OK to think of as &#8220;most stable&#8221;, even if resonance forms don&#8217;t actually exist).\u00a0\u00a0<\/em><\/span><\/li>\n<li>Second is <a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/12\/12\/evaluating-resonance-structures-2-applying-electronegativity\/\">how to break pi bonds<\/a>: if you must break a pi bond to make a resonance structure, do it in a way so that the pair of electrons end up on the more electronegative atom of the pi bond.<\/li>\n<li>Third is that\u00a0<a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/12\/14\/resonance-structures-full-octets-carbocations\/\">full octets<\/a> are preferred if the molecule must have a positive charge.<\/li>\n<li>In this post we&#8217;ll go into more detail on how to evaluate the &#8220;importance&#8221; of resonance structures with a negative charge &#8211; which really boils down to, &#8220;<strong>put the negative charge on the least basic atom<\/strong>&#8220;.<\/li>\n<li>There are quizzes at the bottom of this article that will test you on your understanding of this concept.<\/li>\n<\/ul>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-38642\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2024\/12\/0-summary-determining-importance-of-negatively-charged-resonance-structures-put-negative-charge-on-least-basic-atom.gif\" alt=\"summary- determining importance of negatively charged resonance structures - put negative charge on least basic atom\" width=\"640\" height=\"560\" \/><\/a><\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">All Else Being Equal, A Resonance Structure With A Negative Charge On A Less Basic Atom Will Be More Important Than A Resonance Form With A Negative Charge On A More Basic Atom<\/a><\/li>\n<li><a href=\"#two\">Resonance Structures With Negative Charge, Factor #1: Electronegativity<\/a><\/li>\n<li><a href=\"#three\">Stabilization Of Negative Charges, Factor #2: Polarizability<\/a><\/li>\n<li><a href=\"#four\">Stabilization Of Negative Charges, Factor #3: Inductive effects<\/a><\/li>\n<li><a href=\"#five\">When Multiple Variables Come Into Play, Consult A pKa Table<\/a><\/li>\n<li><a href=\"#six\">Conclusion: Resonance Structures With Negative Charges<\/a><\/li>\n<li><a href=\"#notes\">Notes<\/a><\/li>\n<li><a href=\"#quizzes\">Quiz Yourself!<\/a><\/li>\n<\/ol>\n<hr \/>\n<h2><a id=\"one\"><\/a>1. All Else Being Equal, A Resonance Structure With A Negative Charge On A Less Basic Atom Will Be More Important Than A Resonance Form With A Negative Charge On A More Basic Atom<\/h2>\n<p><img decoding=\"async\" class=\"alignnone wp-image-42808\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/1-determining-best-resonance-form-all-else-being-equal-put-negative-charge-on-less-basic-atom-use-acidity-trends.gif\" alt=\"determining best resonance form all else being equal put negative charge on less basic atom use acidity trends\" width=\"639\" height=\"275\" \/><\/a><\/p>\n<p>You could argue that this definition is circular, because\u00a0 basicity is essentially a <em>measure<\/em> of the stability of an anion. OK, fine. <strong>The more stable an anion is, the less basic it is.\u00a0<\/strong> So how do we go about finding out information on basicity? My suggestion is to visit your best friend,<strong> <a href=\"https:\/\/www.masterorganicchemistry.com\/2010\/06\/18\/know-your-pkas\/\" target=\"_blank\" rel=\"noopener noreferrer\">the pK<sub>a<\/sub> table.<\/a><\/strong> Or you could familiarize yourself with the<strong> <a href=\"https:\/\/www.masterorganicchemistry.com\/2010\/09\/22\/five-key-factors-that-influence-acidity\/\" target=\"_blank\" rel=\"noopener noreferrer\">key trends that affect acidity<\/a><\/strong>, and apply these concepts to resonance forms.<\/p>\n<p>Let&#8217;s go these trends them one by one.<\/p>\n<h2><strong><a id=\"two\"><\/a>2. Resonance Structures With Negative Charge, Factor #1: Electronegativity<\/strong><\/h2>\n<p>Recall that basicity decreases as the electronegativity of an atom increases.<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-42809\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/2-finding-best-resonance-form-apply-acidity-trends-electronegativity-basicity-decreases-with-increasing-electronegativity-across-row.gif\" alt=\"finding best resonance form apply acidity trends electronegativity basicity decreases with increasing electronegativity across row\" width=\"640\" height=\"385\" \/><\/a><\/p>\n<p>That means that in comparing two resonance forms of equal charge, we can determine which is more stable by examining the electronegativity. In the examples above, we can tell that the resonance forms on the left are more stable than the resonance forms on the right, since the electronegativity of O &gt; N and also O &gt; C. There are a lot of chemical structures that have resonance forms with alternating charges on C and N (or O), so this is a particularly useful rule.<\/p>\n<h2><strong><a id=\"three\"><\/a>3. Stabilization Of Negative Charges, Factor #2: Polarizability<\/strong><\/h2>\n<p>The basicity of an atom decreases as the polarizability increases. This trend especially applies for atoms in the same column of the periodic table, such as O and S.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-42810\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/3-determine-best-reosnance-form-apply-acidity-trends-for-anion-stability-polarizability.gif\" alt=\"determine best resonance form apply acidity trends for anion stability polarizability\" width=\"639\" height=\"319\" \/><\/a><\/p>\n<h2><strong><a id=\"four\"><\/a>4. Stabilization Of Negative Charges, Factor #3: Inductive effects<\/strong><\/h2>\n<p>Basicity decreases as the negative charge is stabilized by adjacent electron withdrawing groups. So in the cases below, the more stable resonance form is the one where the negative charge is on the atom with the extra electron withdrawing groups.<\/p>\n<p><strong><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-42811\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/4-apply-acidity-trends-to-determine-best-resonance-form-induction-least-basic-atom.gif\" alt=\"apply acidity trends to determine best resonance form induction least basic atom\" width=\"640\" height=\"360\" \/><\/a><\/strong><\/p>\n<h2><a id=\"five\"><\/a>5. When Multiple Variables Come Into Play, Use A pK<sub>a<\/sub> Table<\/h2>\n<p><strong>But it ain&#8217;t always straightforward. <\/strong>Organic chemistry being what it is, it&#8217;s common to have situations where we have to weigh the effects of multiple variables. Like in these examples.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-42812\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/5-determining-best-resonance-form-anion-sometimes-multiple-variables-compete-cyanate-diazo-nitrile-enolates-thiocyanates.gif\" alt=\"determining best resonance form anion sometimes multiple variables compete cyanate diazo nitrile enolates thiocyanates\" width=\"640\" height=\"301\" \/><\/a><\/p>\n<p>What do we do here? <strong>We rely on experimental results.<\/strong> One body of work in this area is the <a href=\"https:\/\/www.masterorganicchemistry.com\/2010\/09\/29\/how-to-use-a-pka-table\/\" target=\"_blank\" rel=\"noopener noreferrer\">pK<sub>a<\/sub> table<\/a>, an experimentally derived guide to the multi-variable dependent phenomenon of acidity. Another is to compute the relative energies computationally. Or, a third is simply to apply the 4 principles we&#8217;ve discussed earlier to the situation at hand and see which act in the same direction and which oppose. At least 3 of the examples here should be fairly straightforward to figure out .<\/p>\n<h2><a id=\"six\"><\/a>6. Conclusion: Resonance Structures With Negative Charges<\/h2>\n<p>So to make a long story short, as I&#8217;ve said many times before, the <a href=\"https:\/\/www.masterorganicchemistry.com\/2010\/06\/18\/know-your-pkas\/\">pK<sub>a<\/sub> table is your friend<\/a>. For three good reasons.<\/p>\n<p><strong>1.\u00a0<\/strong>It tells you about the <strong>relative strengths of acids and bases<\/strong> (itself very important)<\/p>\n<p><strong>2.\u00a0<\/strong> It gives you an idea of <strong>which atoms will bear negative charge the best<\/strong> (useful for determining the stability of resonance structures). (Weakly basic atoms bear negative charge the best.)<\/p>\n<p><strong>3.\u00a0<\/strong> When you learn about substitution and elimination reactions,\u00a0 it also is the Rosetta Stone for determining <a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/04\/12\/what-makes-a-good-leaving-group\/\">leaving group ability<\/a>. (Good leaving groups = weak bases)<\/p>\n<p><strong>Next Post:<\/strong>\u00a0<a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/12\/14\/evaluating-resonance-forms-4-positive-charges\/\">Evaluating Resonance Forms (4): Where to put the positive charges?<\/a><\/p>\n<hr \/>\n<h2><strong><a id=\"notes\"><\/a>Notes<\/strong><\/h2>\n<div class=\"related-articles\"><p><strong>Related Articles<\/strong><\/p><ul><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/12\/14\/evaluating-resonance-forms-4-positive-charges\/\" class=\"\"><span>Evaluating Resonance Structures With Positive Charge<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2022\/10\/27\/saponification-of-esters\/\" class=\"\"><span>Evaluating Resonance Forms (1) \u2013 The Rule of Least Charges<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/12\/12\/evaluating-resonance-structures-2-applying-electronegativity\/\" class=\"\"><span>How To Find The Best Resonance Structure By Applying Electronegativity<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/01\/10\/common-mistakes-how-not-to-draw-resonance-curved-arrows\/\" class=\"\"><span>Drawing Resonance Structures: 3 Common Mistakes To Avoid<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/12\/22\/in-summary-resonance\/\" class=\"\"><span>In Summary: Evaluating Resonance Structures<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/01\/24\/conjugation-and-resonance\/\" class=\"\"><span>Conjugation And Resonance In Organic Chemistry<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/organic-chemistry-practice-problems\/resonance-structures-practice\/\" class=\"\"><span>Resonance Structures Practice (MOC Membership)<\/span><\/a><\/li><\/ul><\/div>\n<p><strong>Note 1<\/strong>: What about hybridization? Doesn&#8217;t that affect stability of negative charges too? After all, the reason why alkynes are more acidic than alkenes which are more acidic than alkanes is because the ability of orbitals to stabilize negative charge increases as increase the amount of s character [<em>sp<\/em><sup>3<\/sup> to <em>sp<\/em><sup>2<\/sup> to <em>sp<\/em> ]. So shouldn&#8217;t that apply, for example, in the instance below?<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14078\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/F1-hybridization-anion-trends-do-not-apply-because-resonance-hybrid-averages-hybridization-of-atoms-azide-ion-is-great-example.gif\" alt=\"F1-hybridization-anion-trends-do-not-apply-because-resonance-hybrid-averages-hybridization-of-atoms-azide-ion-is-great-example\" width=\"630\" height=\"409\" \/><\/p>\n<p>From examining these two resonance forms we might be tempted to believe that the nitrogen on the left (the one bearing a hydrogen) is sp<sup>2<\/sup> in one version and sp<sup>3<\/sup>\u00a0in another.<\/p>\n<p><strong>\u00a0<\/strong>If you think about what resonance forms represent, however &#8211; different ways of depicting electron density &#8211;\u00a0\u00a0you will realize that\u00a0<strong>this can not actually the case\u00a0<\/strong>since that would involve moving atoms around [re-hybridizing from\u00a0sp<sup>2<\/sup> (trigonal planar) to sp<sup>3<\/sup> (tetrahedral). ].<\/p>\n<p>Both nitrogen atoms are, in fact,\u00a0sp<sup>2<\/sup>\u00a0hybridized, and their stabilities cannot be distinguished based on this characteristic. [<span style=\"color: #993366;\"><em>Thank you to reader Brian E. for correcting an earlier version of this post. In fact, Brian informs me that calculations indicate the right-hand resonance form makes a significantly higher contribution to the resonance hybrid than does the left-hand resonance form<\/em><\/span>].<\/p>\n<hr \/>\n<h2><a id=\"quizzes\"><\/a>Quiz Yourself!<\/h2>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/3662-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/3664-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/3666-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n","protected":false},"excerpt":{"rendered":"<p>Evaluating Resonance Structures With Negative Charges: Some Key Principles So far in discussing resonance forms we&#8217;ve mentioned three important principles that govern which resonance form <\/p>\n","protected":false},"author":1,"featured_media":38642,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1406],"tags":[177,298,399,398,389,379,344,336,267],"post_folder":[],"class_list":["post-3577","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-bonding-structure-resonance","tag-basicity","tag-curved-arrows","tag-hybridization","tag-minimize-charges","tag-negative-charge","tag-opposite-charges-attract","tag-pi-bonds","tag-polarizability","tag-resonance"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Evaluating Resonance Forms: Where To Put Negative Charges<\/title>\n<meta name=\"description\" content=\"When evaluating resonance structures with negative charges, the &quot;best&quot; resonance structure will have the negative charge on the least basic atom.\" \/>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/www.masterorganicchemistry.com\/2011\/12\/13\/resonance-structure-negative-charge-least-basic-atom\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Evaluating Resonance Forms: Where To Put Negative Charges\" \/>\n<meta property=\"og:description\" content=\"When evaluating resonance structures with negative charges, the &quot;best&quot; resonance structure will have the negative charge on the least basic atom.\" \/>\n<meta property=\"og:url\" content=\"https:\/\/www.masterorganicchemistry.com\/2011\/12\/13\/resonance-structure-negative-charge-least-basic-atom\/\" \/>\n<meta property=\"og:site_name\" content=\"Master Organic Chemistry\" \/>\n<meta property=\"article:publisher\" content=\"https:\/\/www.facebook.com\/Master-Organic-Chemistry-242610599108055\/\" \/>\n<meta property=\"article:published_time\" content=\"2011-12-13T12:00:39+00:00\" \/>\n<meta property=\"article:modified_time\" content=\"2026-01-16T20:35:36+00:00\" \/>\n<meta property=\"og:image\" content=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2024\/12\/0-summary-determining-importance-of-negatively-charged-resonance-structures-put-negative-charge-on-least-basic-atom.gif\" \/>\n\t<meta property=\"og:image:width\" content=\"882\" \/>\n\t<meta property=\"og:image:height\" content=\"772\" \/>\n\t<meta property=\"og:image:type\" content=\"image\/gif\" \/>\n<meta name=\"author\" content=\"James Ashenhurst\" \/>\n<meta name=\"twitter:card\" content=\"summary_large_image\" \/>\n<meta name=\"twitter:label1\" content=\"Written by\" \/>\n\t<meta name=\"twitter:data1\" content=\"James Ashenhurst\" \/>\n\t<meta name=\"twitter:label2\" content=\"Est. reading time\" \/>\n\t<meta name=\"twitter:data2\" content=\"7 minutes\" \/>\n<script type=\"application\/ld+json\" class=\"yoast-schema-graph\">{\"@context\":\"https:\\\/\\\/schema.org\",\"@graph\":[{\"@type\":\"Article\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2011\\\/12\\\/13\\\/resonance-structure-negative-charge-least-basic-atom\\\/#article\",\"isPartOf\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2011\\\/12\\\/13\\\/resonance-structure-negative-charge-least-basic-atom\\\/\"},\"author\":{\"name\":\"James Ashenhurst\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#\\\/schema\\\/person\\\/78d83ec7d02b4b7365bade2cedaef80c\"},\"headline\":\"Resonance Structures: Negative Charges Are Best Placed On The Least Basic Atom\",\"datePublished\":\"2011-12-13T12:00:39+00:00\",\"dateModified\":\"2026-01-16T20:35:36+00:00\",\"mainEntityOfPage\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2011\\\/12\\\/13\\\/resonance-structure-negative-charge-least-basic-atom\\\/\"},\"wordCount\":1078,\"commentCount\":23,\"publisher\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#organization\"},\"image\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2011\\\/12\\\/13\\\/resonance-structure-negative-charge-least-basic-atom\\\/#primaryimage\"},\"thumbnailUrl\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/wp-content\\\/uploads\\\/2024\\\/12\\\/0-summary-determining-importance-of-negatively-charged-resonance-structures-put-negative-charge-on-least-basic-atom.gif\",\"keywords\":[\"basicity\",\"curved arrows\",\"hybridization\",\"minimize charges\",\"negative charge\",\"opposite charges attract\",\"pi bonds\",\"polarizability\",\"resonance\"],\"articleSection\":[\"Bonding, Structure, and Resonance\"],\"inLanguage\":\"en-US\",\"potentialAction\":[{\"@type\":\"CommentAction\",\"name\":\"Comment\",\"target\":[\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2011\\\/12\\\/13\\\/resonance-structure-negative-charge-least-basic-atom\\\/#respond\"]}]},{\"@type\":\"WebPage\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2011\\\/12\\\/13\\\/resonance-structure-negative-charge-least-basic-atom\\\/\",\"url\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2011\\\/12\\\/13\\\/resonance-structure-negative-charge-least-basic-atom\\\/\",\"name\":\"Evaluating Resonance Forms: Where To Put Negative Charges\",\"isPartOf\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#website\"},\"primaryImageOfPage\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2011\\\/12\\\/13\\\/resonance-structure-negative-charge-least-basic-atom\\\/#primaryimage\"},\"image\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2011\\\/12\\\/13\\\/resonance-structure-negative-charge-least-basic-atom\\\/#primaryimage\"},\"thumbnailUrl\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/wp-content\\\/uploads\\\/2024\\\/12\\\/0-summary-determining-importance-of-negatively-charged-resonance-structures-put-negative-charge-on-least-basic-atom.gif\",\"datePublished\":\"2011-12-13T12:00:39+00:00\",\"dateModified\":\"2026-01-16T20:35:36+00:00\",\"description\":\"When evaluating resonance structures with negative charges, the \\\"best\\\" resonance structure will have the negative charge on the least basic atom.\",\"breadcrumb\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2011\\\/12\\\/13\\\/resonance-structure-negative-charge-least-basic-atom\\\/#breadcrumb\"},\"inLanguage\":\"en-US\",\"potentialAction\":[{\"@type\":\"ReadAction\",\"target\":[\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2011\\\/12\\\/13\\\/resonance-structure-negative-charge-least-basic-atom\\\/\"]}]},{\"@type\":\"ImageObject\",\"inLanguage\":\"en-US\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2011\\\/12\\\/13\\\/resonance-structure-negative-charge-least-basic-atom\\\/#primaryimage\",\"url\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/wp-content\\\/uploads\\\/2024\\\/12\\\/0-summary-determining-importance-of-negatively-charged-resonance-structures-put-negative-charge-on-least-basic-atom.gif\",\"contentUrl\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/wp-content\\\/uploads\\\/2024\\\/12\\\/0-summary-determining-importance-of-negatively-charged-resonance-structures-put-negative-charge-on-least-basic-atom.gif\",\"width\":882,\"height\":772,\"caption\":\"summary- determining importance of negatively charged resonance structures - put negative charge on least basic atom\"},{\"@type\":\"BreadcrumbList\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2011\\\/12\\\/13\\\/resonance-structure-negative-charge-least-basic-atom\\\/#breadcrumb\",\"itemListElement\":[{\"@type\":\"ListItem\",\"position\":1,\"name\":\"Home\",\"item\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/\"},{\"@type\":\"ListItem\",\"position\":2,\"name\":\"Resonance Structures: Negative Charges Are Best Placed On The Least Basic Atom\"}]},{\"@type\":\"WebSite\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#website\",\"url\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/\",\"name\":\"Master Organic Chemistry\",\"description\":\"\",\"publisher\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#organization\"},\"potentialAction\":[{\"@type\":\"SearchAction\",\"target\":{\"@type\":\"EntryPoint\",\"urlTemplate\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/?s={search_term_string}\"},\"query-input\":{\"@type\":\"PropertyValueSpecification\",\"valueRequired\":true,\"valueName\":\"search_term_string\"}}],\"inLanguage\":\"en-US\"},{\"@type\":\"Organization\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#organization\",\"name\":\"Master Organic Chemistry\",\"url\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/\",\"logo\":{\"@type\":\"ImageObject\",\"inLanguage\":\"en-US\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#\\\/schema\\\/logo\\\/image\\\/\",\"url\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/wp-content\\\/uploads\\\/2019\\\/04\\\/cutmypic.png\",\"contentUrl\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/wp-content\\\/uploads\\\/2019\\\/04\\\/cutmypic.png\",\"width\":225,\"height\":225,\"caption\":\"Master Organic Chemistry\"},\"image\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#\\\/schema\\\/logo\\\/image\\\/\"},\"sameAs\":[\"https:\\\/\\\/www.facebook.com\\\/Master-Organic-Chemistry-242610599108055\\\/\"]},{\"@type\":\"Person\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#\\\/schema\\\/person\\\/78d83ec7d02b4b7365bade2cedaef80c\",\"name\":\"James Ashenhurst\",\"image\":{\"@type\":\"ImageObject\",\"inLanguage\":\"en-US\",\"@id\":\"https:\\\/\\\/secure.gravatar.com\\\/avatar\\\/f9e9df435875e5e6b0bdff6b8522a7279d5717644b3efa7299da22c837bf9fcf?s=96&d=retro&r=g\",\"url\":\"https:\\\/\\\/secure.gravatar.com\\\/avatar\\\/f9e9df435875e5e6b0bdff6b8522a7279d5717644b3efa7299da22c837bf9fcf?s=96&d=retro&r=g\",\"contentUrl\":\"https:\\\/\\\/secure.gravatar.com\\\/avatar\\\/f9e9df435875e5e6b0bdff6b8522a7279d5717644b3efa7299da22c837bf9fcf?s=96&d=retro&r=g\",\"caption\":\"James Ashenhurst\"},\"description\":\"Ph.D. 2006, McGill University (James L. Gleason). Postdoctoral Associate, 2008-2010, Massachusetts Institute of Technology (M. Movassaghi). Founder, Master Organic Chemistry, 2010-present.\",\"sameAs\":[\"https:\\\/\\\/www.masterorganicchemistry.com\\\/about\\\/\"],\"url\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/author\\\/james\\\/\"}]}<\/script>\n<!-- \/ Yoast SEO plugin. -->","yoast_head_json":{"title":"Evaluating Resonance Forms: Where To Put Negative Charges","description":"When evaluating resonance structures with negative charges, the \"best\" resonance structure will have the negative charge on the least basic atom.","robots":{"index":"index","follow":"follow","max-snippet":"max-snippet:-1","max-image-preview":"max-image-preview:large","max-video-preview":"max-video-preview:-1"},"canonical":"https:\/\/www.masterorganicchemistry.com\/2011\/12\/13\/resonance-structure-negative-charge-least-basic-atom\/","og_locale":"en_US","og_type":"article","og_title":"Evaluating Resonance Forms: Where To Put Negative Charges","og_description":"When evaluating resonance structures with negative charges, the \"best\" resonance structure will have the negative charge on the least basic atom.","og_url":"https:\/\/www.masterorganicchemistry.com\/2011\/12\/13\/resonance-structure-negative-charge-least-basic-atom\/","og_site_name":"Master Organic Chemistry","article_publisher":"https:\/\/www.facebook.com\/Master-Organic-Chemistry-242610599108055\/","article_published_time":"2011-12-13T12:00:39+00:00","article_modified_time":"2026-01-16T20:35:36+00:00","og_image":[{"width":882,"height":772,"url":"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2024\/12\/0-summary-determining-importance-of-negatively-charged-resonance-structures-put-negative-charge-on-least-basic-atom.gif","type":"image\/gif"}],"author":"James Ashenhurst","twitter_card":"summary_large_image","twitter_misc":{"Written by":"James Ashenhurst","Est. reading time":"7 minutes"},"schema":{"@context":"https:\/\/schema.org","@graph":[{"@type":"Article","@id":"https:\/\/www.masterorganicchemistry.com\/2011\/12\/13\/resonance-structure-negative-charge-least-basic-atom\/#article","isPartOf":{"@id":"https:\/\/www.masterorganicchemistry.com\/2011\/12\/13\/resonance-structure-negative-charge-least-basic-atom\/"},"author":{"name":"James Ashenhurst","@id":"https:\/\/www.masterorganicchemistry.com\/#\/schema\/person\/78d83ec7d02b4b7365bade2cedaef80c"},"headline":"Resonance Structures: Negative Charges Are Best Placed On The Least Basic Atom","datePublished":"2011-12-13T12:00:39+00:00","dateModified":"2026-01-16T20:35:36+00:00","mainEntityOfPage":{"@id":"https:\/\/www.masterorganicchemistry.com\/2011\/12\/13\/resonance-structure-negative-charge-least-basic-atom\/"},"wordCount":1078,"commentCount":23,"publisher":{"@id":"https:\/\/www.masterorganicchemistry.com\/#organization"},"image":{"@id":"https:\/\/www.masterorganicchemistry.com\/2011\/12\/13\/resonance-structure-negative-charge-least-basic-atom\/#primaryimage"},"thumbnailUrl":"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2024\/12\/0-summary-determining-importance-of-negatively-charged-resonance-structures-put-negative-charge-on-least-basic-atom.gif","keywords":["basicity","curved arrows","hybridization","minimize charges","negative charge","opposite charges attract","pi bonds","polarizability","resonance"],"articleSection":["Bonding, Structure, and Resonance"],"inLanguage":"en-US","potentialAction":[{"@type":"CommentAction","name":"Comment","target":["https:\/\/www.masterorganicchemistry.com\/2011\/12\/13\/resonance-structure-negative-charge-least-basic-atom\/#respond"]}]},{"@type":"WebPage","@id":"https:\/\/www.masterorganicchemistry.com\/2011\/12\/13\/resonance-structure-negative-charge-least-basic-atom\/","url":"https:\/\/www.masterorganicchemistry.com\/2011\/12\/13\/resonance-structure-negative-charge-least-basic-atom\/","name":"Evaluating Resonance Forms: Where To Put Negative Charges","isPartOf":{"@id":"https:\/\/www.masterorganicchemistry.com\/#website"},"primaryImageOfPage":{"@id":"https:\/\/www.masterorganicchemistry.com\/2011\/12\/13\/resonance-structure-negative-charge-least-basic-atom\/#primaryimage"},"image":{"@id":"https:\/\/www.masterorganicchemistry.com\/2011\/12\/13\/resonance-structure-negative-charge-least-basic-atom\/#primaryimage"},"thumbnailUrl":"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2024\/12\/0-summary-determining-importance-of-negatively-charged-resonance-structures-put-negative-charge-on-least-basic-atom.gif","datePublished":"2011-12-13T12:00:39+00:00","dateModified":"2026-01-16T20:35:36+00:00","description":"When evaluating resonance structures with negative charges, the \"best\" resonance structure will have the negative charge on the least basic atom.","breadcrumb":{"@id":"https:\/\/www.masterorganicchemistry.com\/2011\/12\/13\/resonance-structure-negative-charge-least-basic-atom\/#breadcrumb"},"inLanguage":"en-US","potentialAction":[{"@type":"ReadAction","target":["https:\/\/www.masterorganicchemistry.com\/2011\/12\/13\/resonance-structure-negative-charge-least-basic-atom\/"]}]},{"@type":"ImageObject","inLanguage":"en-US","@id":"https:\/\/www.masterorganicchemistry.com\/2011\/12\/13\/resonance-structure-negative-charge-least-basic-atom\/#primaryimage","url":"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2024\/12\/0-summary-determining-importance-of-negatively-charged-resonance-structures-put-negative-charge-on-least-basic-atom.gif","contentUrl":"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2024\/12\/0-summary-determining-importance-of-negatively-charged-resonance-structures-put-negative-charge-on-least-basic-atom.gif","width":882,"height":772,"caption":"summary- determining importance of negatively charged resonance structures - put negative charge on least basic atom"},{"@type":"BreadcrumbList","@id":"https:\/\/www.masterorganicchemistry.com\/2011\/12\/13\/resonance-structure-negative-charge-least-basic-atom\/#breadcrumb","itemListElement":[{"@type":"ListItem","position":1,"name":"Home","item":"https:\/\/www.masterorganicchemistry.com\/"},{"@type":"ListItem","position":2,"name":"Resonance Structures: Negative Charges Are Best Placed On The Least Basic Atom"}]},{"@type":"WebSite","@id":"https:\/\/www.masterorganicchemistry.com\/#website","url":"https:\/\/www.masterorganicchemistry.com\/","name":"Master Organic Chemistry","description":"","publisher":{"@id":"https:\/\/www.masterorganicchemistry.com\/#organization"},"potentialAction":[{"@type":"SearchAction","target":{"@type":"EntryPoint","urlTemplate":"https:\/\/www.masterorganicchemistry.com\/?s={search_term_string}"},"query-input":{"@type":"PropertyValueSpecification","valueRequired":true,"valueName":"search_term_string"}}],"inLanguage":"en-US"},{"@type":"Organization","@id":"https:\/\/www.masterorganicchemistry.com\/#organization","name":"Master Organic Chemistry","url":"https:\/\/www.masterorganicchemistry.com\/","logo":{"@type":"ImageObject","inLanguage":"en-US","@id":"https:\/\/www.masterorganicchemistry.com\/#\/schema\/logo\/image\/","url":"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/04\/cutmypic.png","contentUrl":"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/04\/cutmypic.png","width":225,"height":225,"caption":"Master Organic Chemistry"},"image":{"@id":"https:\/\/www.masterorganicchemistry.com\/#\/schema\/logo\/image\/"},"sameAs":["https:\/\/www.facebook.com\/Master-Organic-Chemistry-242610599108055\/"]},{"@type":"Person","@id":"https:\/\/www.masterorganicchemistry.com\/#\/schema\/person\/78d83ec7d02b4b7365bade2cedaef80c","name":"James Ashenhurst","image":{"@type":"ImageObject","inLanguage":"en-US","@id":"https:\/\/secure.gravatar.com\/avatar\/f9e9df435875e5e6b0bdff6b8522a7279d5717644b3efa7299da22c837bf9fcf?s=96&d=retro&r=g","url":"https:\/\/secure.gravatar.com\/avatar\/f9e9df435875e5e6b0bdff6b8522a7279d5717644b3efa7299da22c837bf9fcf?s=96&d=retro&r=g","contentUrl":"https:\/\/secure.gravatar.com\/avatar\/f9e9df435875e5e6b0bdff6b8522a7279d5717644b3efa7299da22c837bf9fcf?s=96&d=retro&r=g","caption":"James Ashenhurst"},"description":"Ph.D. 2006, McGill University (James L. Gleason). Postdoctoral Associate, 2008-2010, Massachusetts Institute of Technology (M. Movassaghi). Founder, Master Organic Chemistry, 2010-present.","sameAs":["https:\/\/www.masterorganicchemistry.com\/about\/"],"url":"https:\/\/www.masterorganicchemistry.com\/author\/james\/"}]}},"_links":{"self":[{"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/posts\/3577","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/comments?post=3577"}],"version-history":[{"count":0,"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/posts\/3577\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/media\/38642"}],"wp:attachment":[{"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/media?parent=3577"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/categories?post=3577"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/tags?post=3577"},{"taxonomy":"post_folder","embeddable":true,"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/post_folder?post=3577"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}