{"id":2941,"date":"2011-11-15T12:00:11","date_gmt":"2011-11-15T12:00:11","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=2941"},"modified":"2025-11-15T09:16:18","modified_gmt":"2025-11-15T15:16:18","slug":"how_to_use_electronegativity","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2011\/11\/15\/how_to_use_electronegativity\/","title":{"rendered":"How To Use Electronegativity To Determine Electron Density (and why NOT to trust formal charge)"},"content":{"rendered":"<p><strong>How To Determine Partial Charges<\/strong><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/11\/09\/the-second-most-important-question-to-ask-when-learning-a-new-reaction\/\">Last time <\/a>we talked about how electrons are the &#8220;currency&#8221; of chemistry and every reaction is a transaction of electrons between atoms. That means that if we really want to understand a reaction, we have to understand where the electrons are (and aren&#8217;t).<\/p>\n<p>There&#8217;s two factors to employ when doing this. The first is <strong>electronegativity<\/strong>. That&#8217;s what today&#8217;s post is about: <strong>using electronegativity to determine electron densities<\/strong>. (<span style=\"color: #993366;\"><em>The second is <a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/2011\/11\/23\/introduction-to-resonance\/\">resonance<\/a> &#8211; more on that in the next article<\/em><\/span>)<\/p>\n<p>I&#8217;m assuming you know how to draw Lewis structures and understand the concepts of electronegativity and <a href=\"https:\/\/www.masterorganicchemistry.com\/2010\/09\/24\/how-to-calculate-formal-charge\/\"><em>formal charge<\/em><\/a>, as well as being able to interpret line drawings, but that&#8217;s it.\u00a0 If you&#8217;re not at that level, back up and read up on those concepts.<\/p>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-38683\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2025\/01\/0-Summary-how-to-use-elecronegativity-to-determine-electron-density-dipoles-formal-charge-doesnt-tell-you-electron-density.gif\" alt=\"Summary-how to use elecronegativity to determine electron density dipoles formal charge doesnt tell you electron density\" width=\"640\" height=\"740\" \/><\/a><\/p>\n<p><strong>Table Of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">How Do We Tell Where The Electrons Are? First, Draw The Lewis Structure<\/a><\/li>\n<li><a href=\"#two\">Second, Apply Electronegativity To Determine Partial Charges<\/a><\/li>\n<li><a href=\"#three\">Formal Charge Is NOT The Same As Electron Density<\/a><\/li>\n<li><a href=\"#four\">Bottom Line: Use Relative Electronegativities, Not Formal Charges, To Determine Electron Densities<\/a><\/li>\n<li><a href=\"#notes\">Notes<\/a><\/li>\n<\/ol>\n<hr \/>\n<h2><a id=\"one\"><\/a>1. How Do We Tell Where The Electrons Are? First, Draw The Lewis Structure<\/h2>\n<p>OK. Let&#8217;s start with the first question: how do we tell where the electrons are in a molecule?<\/p>\n<p>The first skill is being able to draw proper Lewis structures for a molecule. <strong>To succeed in organic chemistry you absolutely need to be able to do this in your sleep. <\/strong>The Lewis structure should account for all the electrons around an atom, including the often-hidden lone pairs of electrons if applicable. Let&#8217;s have a look.<\/p>\n<p><div class=\"wq-quiz-wrapper\" data-id=\"42718\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"42718\"] {\n--wq-question-width: 100%;\n--wq-question-color: #009cff;\n--wq-question-height: auto;\n--wq-font-color: #444;\n}\n\n\t\t\t.wq-quiz-wrapper[data-id=\"42718\"] {\n\t\t\t\t--wq-question-width: 600px;\n\t\t\t}\n\n\t\t\t@media screen and (max-width: 600px) {\n\t\t\t\t.wq-quiz-wrapper[data-id=\"42718\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-42718\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-42718 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"42718\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-zj0ta\" data-id=\"zj0ta\">\n\n\t\n\t<div class=\"item_top\">\n\t\t<div class=\"title_container\">\n\t\t\t<div class=\"wq_questionTextCtr\">\n\t\t\t\t<h4 class=\"wq-question-title\"><\/h4>\n\t\t\t<\/div>\n\t\t<\/div>\n\t<\/div>\n\n\t<div class=\"card \">\n\t\t<div class=\"front\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/3550-Front.gif\" \/>\n\t\t\n\t\t\n\t\n\t\n\t\t\t<span class=\"top-desc\">Click to Flip<\/span>\n\t<\/div>\n\t\t<div class=\"back\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/3550-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper --><br \/>\n<div class=\"wq-quiz-wrapper\" data-id=\"42719\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"42719\"] {\n--wq-question-width: 100%;\n--wq-question-color: #009cff;\n--wq-question-height: auto;\n--wq-font-color: #444;\n}\n\n\t\t\t.wq-quiz-wrapper[data-id=\"42719\"] {\n\t\t\t\t--wq-question-width: 600px;\n\t\t\t}\n\n\t\t\t@media screen and (max-width: 600px) {\n\t\t\t\t.wq-quiz-wrapper[data-id=\"42719\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-42719\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-42719 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"42719\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-4x31b\" data-id=\"4x31b\">\n\n\t\n\t<div class=\"item_top\">\n\t\t<div class=\"title_container\">\n\t\t\t<div class=\"wq_questionTextCtr\">\n\t\t\t\t<h4 class=\"wq-question-title\"><\/h4>\n\t\t\t<\/div>\n\t\t<\/div>\n\t<\/div>\n\n\t<div class=\"card \">\n\t\t<div class=\"front\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/3551-Front.gif\" \/>\n\t\t\n\t\t\n\t\n\t\n\t\t\t<span class=\"top-desc\">Click to Flip<\/span>\n\t<\/div>\n\t\t<div class=\"back\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/3551-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper --><br \/>\n<div class=\"wq-quiz-wrapper\" data-id=\"42720\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"42720\"] {\n--wq-question-width: 100%;\n--wq-question-color: #009cff;\n--wq-question-height: auto;\n--wq-font-color: #444;\n}\n\n\t\t\t.wq-quiz-wrapper[data-id=\"42720\"] {\n\t\t\t\t--wq-question-width: 600px;\n\t\t\t}\n\n\t\t\t@media screen and (max-width: 600px) {\n\t\t\t\t.wq-quiz-wrapper[data-id=\"42720\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-42720\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-42720 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"42720\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-w4buo\" data-id=\"w4buo\">\n\n\t\n\t<div class=\"item_top\">\n\t\t<div class=\"title_container\">\n\t\t\t<div class=\"wq_questionTextCtr\">\n\t\t\t\t<h4 class=\"wq-question-title\"><\/h4>\n\t\t\t<\/div>\n\t\t<\/div>\n\t<\/div>\n\n\t<div class=\"card \">\n\t\t<div class=\"front\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/3552-Front.gif\" \/>\n\t\t\n\t\t\n\t\n\t\n\t\t\t<span class=\"top-desc\">Click to Flip<\/span>\n\t<\/div>\n\t\t<div class=\"back\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/3552-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper --><\/p>\n<p>Some molecules don&#8217;t have &#8220;hidden&#8221; lone pairs. Make sure you can see this too!<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-42721\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2025\/11\/4-Molecules-that-have-formal-charges-but-no-hidden-lone-pairs-in-Lewis-structure.gif\" alt=\"Molecules that have formal charges but no hidden lone pairs in Lewis structure\" width=\"600\" height=\"141\" \/><\/a><\/p>\n<h2><a id=\"two\"><\/a>2. Second, Apply Electronegativity To Determine Partial Charges<\/h2>\n<p>The second skill lies in being able to apply <strong>electronegativity<\/strong> to determine <strong>partial charges<\/strong> in bonds (<span style=\"color: #993366;\"><em>See article: <a href=\"https:\/\/www.masterorganicchemistry.com\/2025\/10\/17\/dipole-moments-and-dipoles\/\">Dipoles and Dipole Moments<\/a><\/em><\/span>)<\/p>\n<p>See, our drawings of chemical structures can sometimes get in the way of what is <strong>really going on with the electrons.\u00a0<\/strong><\/p>\n<p>If we just paid attention to the drawings themselves, the lines we draw between atoms &#8211; &#8220;covalent bonds&#8221; &#8211; are electron pairs that are shared equally between the two.<\/p>\n<p>However, the difference between the idealized sharing of electrons in a covalent bond versus the reality of different electron densities is, to use an analogy, not unlike the difference between a utopian socialist worker-state, and Soviet Russia.<\/p>\n<p>Remember electronegativity &#8211; a ranking of an atom&#8217;s &#8220;greed&#8221; for electrons, in other words?<\/p>\n<ul>\n<li>In a covalent bond, the<strong> more electronegative element<\/strong> will have a<strong> greater share<\/strong> of the<strong> bonding electrons<\/strong>, and a <strong>partial <em>negative<\/em> charge<\/strong> (\u03b4-)to reflect this greater electron density.<\/li>\n<li>The <strong>less electronegative element<\/strong> will have a <strong>partial<\/strong> <strong><em>positive<\/em><\/strong> charge (\u03b4+) to reflect the <strong>lack<\/strong> of electron density.<\/li>\n<\/ul>\n<p>Let&#8217;s look at a few simple molecules and analyze the dipoles in their bonds by comparing relative electronegativities.<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-42735\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2025\/11\/5-How-to-use-electronegativities-to-find-electron-densities-and-dipoles.gif\" alt=\"How to use electronegativities to find electron densities and dipoles\" width=\"640\" height=\"289\" \/><\/a><\/p>\n<p><div class=\"wq-quiz-wrapper\" data-id=\"42731\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"42731\"] {\n--wq-question-width: 100%;\n--wq-question-color: #009cff;\n--wq-question-height: auto;\n--wq-font-color: #444;\n}\n\n\t\t\t.wq-quiz-wrapper[data-id=\"42731\"] {\n\t\t\t\t--wq-question-width: 600px;\n\t\t\t}\n\n\t\t\t@media screen and (max-width: 600px) {\n\t\t\t\t.wq-quiz-wrapper[data-id=\"42731\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-42731\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-42731 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"42731\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-3nq6l\" data-id=\"3nq6l\">\n\n\t\n\t<div class=\"item_top\">\n\t\t<div class=\"title_container\">\n\t\t\t<div class=\"wq_questionTextCtr\">\n\t\t\t\t<h4 class=\"wq-question-title\"><\/h4>\n\t\t\t<\/div>\n\t\t<\/div>\n\t<\/div>\n\n\t<div class=\"card \">\n\t\t<div class=\"front\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/3553-Front.gif\" \/>\n\t\t\n\t\t\n\t\n\t\n\t\t\t<span class=\"top-desc\">Click to Flip<\/span>\n\t<\/div>\n\t\t<div class=\"back\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/3553-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper --><br \/>\n<div class=\"wq-quiz-wrapper\" data-id=\"42732\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"42732\"] {\n--wq-question-width: 100%;\n--wq-question-color: #009cff;\n--wq-question-height: auto;\n--wq-font-color: #444;\n}\n\n\t\t\t.wq-quiz-wrapper[data-id=\"42732\"] {\n\t\t\t\t--wq-question-width: 600px;\n\t\t\t}\n\n\t\t\t@media screen and (max-width: 600px) {\n\t\t\t\t.wq-quiz-wrapper[data-id=\"42732\"] .wq_singleQuestionWrapper { width:100% !important; 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height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-42733\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-42733 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"42733\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-1rfk1\" data-id=\"1rfk1\">\n\n\t\n\t<div class=\"item_top\">\n\t\t<div class=\"title_container\">\n\t\t\t<div class=\"wq_questionTextCtr\">\n\t\t\t\t<h4 class=\"wq-question-title\"><\/h4>\n\t\t\t<\/div>\n\t\t<\/div>\n\t<\/div>\n\n\t<div class=\"card \">\n\t\t<div class=\"front\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/3555-Front.gif\" \/>\n\t\t\n\t\t\n\t\n\t\n\t\t\t<span class=\"top-desc\">Click to Flip<\/span>\n\t<\/div>\n\t\t<div class=\"back\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/3555-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper --><br \/>\n<div class=\"wq-quiz-wrapper\" data-id=\"42734\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"42734\"] {\n--wq-question-width: 100%;\n--wq-question-color: #009cff;\n--wq-question-height: auto;\n--wq-font-color: #444;\n}\n\n\t\t\t.wq-quiz-wrapper[data-id=\"42734\"] {\n\t\t\t\t--wq-question-width: 600px;\n\t\t\t}\n\n\t\t\t@media screen and (max-width: 600px) {\n\t\t\t\t.wq-quiz-wrapper[data-id=\"42734\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-42734\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-42734 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"42734\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-9kfyf\" data-id=\"9kfyf\">\n\n\t\n\t<div class=\"item_top\">\n\t\t<div class=\"title_container\">\n\t\t\t<div class=\"wq_questionTextCtr\">\n\t\t\t\t<h4 class=\"wq-question-title\"><\/h4>\n\t\t\t<\/div>\n\t\t<\/div>\n\t<\/div>\n\n\t<div class=\"card \">\n\t\t<div class=\"front\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/3556-Front.gif\" \/>\n\t\t\n\t\t\n\t\n\t\n\t\t\t<span class=\"top-desc\">Click to Flip<\/span>\n\t<\/div>\n\t\t<div class=\"back\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/3556-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper --><\/p>\n<p><span class=\"Apple-style-span\" style=\"color: #000000; -webkit-text-decorations-in-effect: none;\">Why is it important to go through all of this? <\/span><\/p>\n<p><span class=\"Apple-style-span\" style=\"color: #000000; -webkit-text-decorations-in-effect: none;\"><strong>Because in chemical reactions, electrons will flow from areas of high electron density to areas of low electron density. Knowing where the partial charges are is an important first step in determining where the molecule will react. <\/strong><\/span><\/p>\n<p><span class=\"Apple-style-span\" style=\"color: #000000; -webkit-text-decorations-in-effect: none;\">Covalent bonds with large dipoles (i.e. large differences in electronegativity) are worth looking paying attention to: frequently, this will be where the &#8220;action&#8221; is.<\/span><\/p>\n<p>&#8220;Hold on&#8221;, you might say. &#8220;I thought electron densities were reflected by their charges, like in H<sub>3<\/sub>O+, BF<sub>4<\/sub><sup>&#8211;<\/sup>, and NH<sub>2<\/sub><sup>&#8211;<\/sup> !&#8221;<\/p>\n<p>No no no no no. This is one of the first real curveballs that gets thrown at you in organic chemistry, and one that continually gives students fits.<\/p>\n<h2><strong><a id=\"three\"><\/a>3. Formal Charge Is NOT The Same As Electron D<\/strong><strong>ensity\u00a0<\/strong><\/h2>\n<p>&#8220;Formal charge&#8221; gives us a bit of a dilemma.<\/p>\n<p>When a molecule bears a charge (either positive or negative), \u00a0for bookkeeping purposes, we have to denote one atom as &#8220;bearing&#8221; that charge.<\/p>\n<p>However it&#8217;s important to realize that this &#8220;bookkeeping&#8221; is NOT the same as electron density, which is\u00a0\u00a0the real sources of reactivity.<\/p>\n<p>Sure, there are lots of examples of molecules where the charge actually *does* represent the electron density. But then again, there are a lot of counter examples too &#8211; like BH<sub>4<\/sub>(-), NH<sub>4<\/sub>(+), H<sub>3<\/sub>O(+) and others.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-42736\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2025\/11\/10-Formal-charge-is-not-a-reliable-guide-to-electron-density-of-atoms.gif\" alt=\"Formal charge is not a reliable guide to electron density of atoms\" width=\"640\" height=\"412\" \/><\/a><\/p>\n<p>Make sure you understand this because it might be hard to get your head around the first time.<\/p>\n<p>The O in H<sub>3<\/sub>O+ might have a &#8220;formal&#8221; charge of +1, but it is actually the most electron-rich (i.e. negatively charged) atom on the molecule!<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-42737\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2025\/11\/11-Sometimes-formal-charge-aligns-with-actual-electron-density-but-not-always-H3O-BH4.gif\" alt=\"-Sometimes formal charge aligns with actual electron density but not always H3O BH4\" width=\"640\" height=\"647\" \/><\/a><\/p>\n<p>So although the molecule H<sub>3<\/sub>O(+) has a charge of +1, that positive charge \u00a0is actually <strong>not<\/strong>\u00a0<strong>on the oxygen itself,<\/strong> but is &#8220;spread out&#8221; &#8211; dispersed &#8211; around the molecule, but particularly around the hydrogens.(\u00a0<a href=\"http:\/\/academic.reed.edu\/chemistry\/roco\/Potential\/charge_distribution.html\" target=\"_blank\" rel=\"noopener noreferrer\">Click here to see a potential energy map of H<sub>3<\/sub>O(+)<\/a>\u00a0).\u00a0However, for &#8220;book-keeping&#8221; we assign a charge of +1 on the oxygen, because of the underlying assumption in bond diagrams that electrons are shared equally between atoms.<\/p>\n<h2><a id=\"four\"><\/a>4. Bottom Line: Use Relative Electronegativities, Not Formal Charges, To Determine Electron Densities<\/h2>\n<p><strong>Bottom line:<\/strong> if H<sub>3<\/sub>O(+) is reacting with an electron rich species, those electrons will go to the <strong>hydrogens<\/strong> (since they are electron poor), <strong>NOT <\/strong>the oxygen!!<\/p>\n<p><strong>If you use formal charge to determine electron densities you will get screwed over on a regular basis.\u00a0<\/strong><\/p>\n<div>Let&#8217;s finish by <em>applying<\/em>\u00a0this concept toward some potential attractive and repulsive interactions between molecules. These are <strong>not<\/strong> meant to depict actual reactions, although as we will later see, reactions will begin with an attractive interaction between two molecules.<\/div>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-42738\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2025\/11\/12-attractive-interactions-between-partial-charges-can-predict-the-course-of-reactions.gif\" alt=\"attractive interactions between partial charges can predict the course of reactions\" width=\"640\" height=\"433\" \/><\/a><\/p>\n<div>Conversely, where we line up two <em>like<\/em>\u00a0charges (positive-positive and negative-negative) these are sites where repulsion will occur (and reactions between these atoms will not occur).<\/div>\n<div><\/div>\n<div><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-42739\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2025\/11\/13-partial-charges-with-like-charges-will-repel-and-are-a-guide-to-where-reactions-will-not-happen.gif\" alt=\"-partial charges with like charges will repel and are a guide to where reactions will not happen\" width=\"641\" height=\"287\" \/><\/a><\/div>\n<div><\/div>\n<div><strong>Bottom line #2: If you learn electronegativities and how to assign partial charges, you will be always be able to figure out where the electron rich and electron poor areas of a molecule are, and we can apply this toward reactions.\u00a0<\/strong><\/div>\n<div>Things will get a bit more complicated when <em>resonance<\/em>\u00a0is possible.\u00a0\u00a0More on that in the next post.<\/div>\n<p>Note how on the last part of the 3rd slide I threw in some new words &#8211; &#8220;electrophilic&#8221; and &#8220;nucleophilic&#8221; to denote &#8220;electron-poor&#8221; and &#8220;electron-rich&#8221; respectively. Much more on these later.<\/p>\n<p>Here&#8217;s an excellent online resource on the topic of <a href=\"http:\/\/academic.reed.edu\/chemistry\/roco\/Potential\/standard_color_scale.html\">electrostatic potential in organic chemistry<\/a> from Reed College.<\/p>\n<p><strong>Next Post: <\/strong><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/11\/23\/introduction-to-resonance\/\" target=\"_blank\" rel=\"noopener noreferrer\">Introduction to Resonance<\/a><\/p>\n<hr \/>\n<h2><a id=\"notes\"><\/a>Notes<\/h2>\n<div class=\"related-articles\"><p><strong>Related Articles<\/strong><\/p><ul><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/11\/23\/introduction-to-resonance\/\" class=\"\"><span>Introduction to Resonance<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/07\/11\/partial-charges\/\" class=\"\"><span>Partial Charges Give Clues About Electron Flow<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2010\/09\/24\/how-to-calculate-formal-charge\/\" class=\"\"><span>A Key Skill: How to Calculate Formal Charge<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2010\/10\/01\/how-intermolecular-forces-affect-boiling-points\/\" class=\"\"><span>The Four Intermolecular Forces and How They Affect Boiling Points<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/06\/27\/hidden-hydrogens-hidden-lone-pairs-hidden-counterions\/\" class=\"\"><span>Hidden Hydrogens, Hidden Lone Pairs, Hidden Counterions<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/07\/11\/partial-charges\/\" class=\"\"><span>Partial Charges Give Clues About Electron Flow<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/08\/29\/the-most-important-question-to-ask-when-learning-a-new-reaction\/\" class=\"\"><span>The Most Important Question To Ask When Learning a New Reaction<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2025\/10\/17\/dipole-moments-and-dipoles\/\" class=\"\"><span>Dipole Moments and Dipoles<\/span><\/a><\/li><\/ul><\/div>\n","protected":false},"excerpt":{"rendered":"<p>How To Determine Partial Charges Last time we talked about how electrons are the &#8220;currency&#8221; of chemistry and every reaction is a transaction of electrons <\/p>\n","protected":false},"author":1,"featured_media":38683,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1406],"tags":[334,199,213,423,422,418,424],"post_folder":[],"class_list":["post-2941","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-bonding-structure-resonance","tag-electron-density","tag-electronegativity","tag-formal-charge","tag-lewis-structures","tag-lies","tag-partial-charges","tag-polar-covalent-bonds"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>How To Use Electronegativity To Determine Electron Density (and why NOT to trust formal charge) &#8211; Master Organic Chemistry<\/title>\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\/11\/15\/how_to_use_electronegativity\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"How To Use Electronegativity To Determine Electron Density (and why NOT to trust formal charge) &#8211; 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