{"id":10748,"date":"2017-05-12T08:19:12","date_gmt":"2017-05-12T12:19:12","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=10748"},"modified":"2025-11-14T03:39:20","modified_gmt":"2025-11-14T09:39:20","slug":"s-cis-and-s-trans","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2017\/05\/12\/s-cis-and-s-trans\/","title":{"rendered":"s-cis and s-trans"},"content":{"rendered":"<p>&#8220;s-<em>cis<\/em> and s-<em>trans conformations of dienes.&#8221;<\/em> <strong>What does those terms mean?<\/strong><\/p>\n<ul>\n<li>\u00a0The &#8220;<em>s<\/em>&#8211;<em>cis<\/em>&#8221; is a <strong>conformation<\/strong> where both double bonds are on the same side of a sigma bond.<\/li>\n<li>Recall that there is free rotation about <strong>sigma<\/strong> bonds, so we say, &#8220;<em>s-cis<\/em>&#8221; and &#8220;<em>s-trans<\/em>&#8221; to distinguish it from &#8220;<em>cis<\/em>&#8221; and &#8220;<em>trans<\/em>&#8221; <strong>configurations<\/strong> which are locked.<\/li>\n<li>As we&#8217;ll soon see, in the <a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/08\/30\/the-diels-alder-reaction\/\">Diels-Alder reaction<\/a>, it&#8217;s important that the diene be in the &#8220;<em>s<\/em>&#8211;<em>cis&#8221;\u00a0<\/em>conformation, otherwise the two reacting ends are too far apart.<\/li>\n<\/ul>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-34097\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/02\/0-summary-s-cis-and-s-trans-conformations-of-a-diene.gif\" alt=\"summary-s cis and s trans conformations of a diene\" width=\"640\" height=\"534\" \/><\/a><\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">Recall That <em>Cis-<\/em> And\u00a0<em>Trans<\/em>&#8211; Isomers (&#8220;Geometric Isomers&#8221; Cannot Interconvert Without Breaking Bonds<\/a><\/li>\n<li><a href=\"#two\"><i>s-cis<\/i> and <i>s-trans<\/i> Conformations In Butadiene<\/a><\/li>\n<li><a href=\"#three\">The <i>s-trans\u00a0<\/i>Conformation Is Lower In Energy<\/a><\/li>\n<li><a href=\"#four\">Some Dienes Are &#8220;Locked&#8221; In The <i>s-cis<\/i> or <i>s-trans<\/i> Orientation<\/a><\/li>\n<li><a href=\"#five\">Conformations In Amides: (<i>Z<\/i>) and (<i>E<\/i>)<\/a><\/li>\n<li><a href=\"#notes\">Notes<\/a><\/li>\n<li><a href=\"#quizzes\">Quiz Yourself!<\/a><\/li>\n<li><a href=\"#references\">(Advanced) References and Further Reading<\/a><\/li>\n<\/ol>\n<hr \/>\n<h2><strong><a id=\"one\"><\/a>1. Recall That <em>Cis-<\/em> And\u00a0<em>Trans<\/em>&#8211; Isomers (&#8220;Geometric Isomers&#8221; Cannot Interconvert Without Breaking Bonds<\/strong><\/h2>\n<p>Recall <a href=\"https:\/\/www.masterorganicchemistry.com\/2016\/11\/03\/alkene-nomenclature-cis-and-trans-and-e-and-z\/\"><em>cis<\/em> and <em>trans<\/em><\/a>. The reason Aldrich\u00a0Chemical Co. can sell 99%\u00a0<a href=\"http:\/\/www.sigmaaldrich.com\/catalog\/product\/aldrich\/400890?lang=en&amp;region=US\"><em>cis<\/em>-2-butene<\/a> and 99%\u00a0<a href=\"http:\/\/www.sigmaaldrich.com\/catalog\/product\/aldrich\/295086?lang=en&amp;region=US\"><em>trans<\/em>-2-butene <\/a>in separate bottles is because of restricted rotation about the C-C pi bond. Rotation is energetically disfavored since it\u00a0 would destroy the overlap of the adjacent p-orbitals.<\/p>\n<p>We use the\u00a0terms &#8220;<em>cis<\/em>&#8221; and &#8220;<em>trans&#8221;<\/em>\u00a0to distinguish\u00a0the different configurations of hydrogens\u00a0across the C-C pi bond.<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-15625\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-drawing-of-trans-2-butene-and-cis-2-butene-showing-that-they-are-stereoisomers.gif\" alt=\"drawing of trans 2 butene and cis 2 butene showing that they are stereoisomers\" width=\"600\" height=\"172\" \/><\/p>\n<p>In contrast to pi bonds, rotation about single (sigma) bonds happens all the time &#8211; thousands of times per second, in fact.<\/p>\n<p>You might recall that we refer to the different shapes of a molecule that arise through these rotations, &#8220;<a href=\"https:\/\/www.masterorganicchemistry.com\/2010\/11\/11\/on-cats-part-1-conformations-and-configurations\/\">conformations<\/a>&#8220;.<\/p>\n<p>For reasons that will soon become clear, it&#8217;s sometimes helpful to borrow\u00a0the &#8220;<em>cis<\/em>&#8221; and &#8220;<em>trans<\/em>&#8221; terminology for\u00a0naming\u00a0particularly important conformations.<\/p>\n<h2><a id=\"two\"><\/a>2.<em> s-cis<\/em> and <em>s-trans<\/em> Conformations In Butadiene<\/h2>\n<p>A particularly important case comes up with dienes. In butadiene, the two individual pi bonds may be either on the opposite side of the single bond or on the same side of the single bond. It would be incorrect to refer to these as strictly\u00a0<em>trans<\/em> and\u00a0<em>cis<\/em> since these are conformations (dynamic!), not configurations (static). But we can get the best of both worlds if we cheat a bit and use the prefix\u00a0<em>&#8220;s&#8221;\u00a0<\/em>(for &#8220;sigma&#8221; , or &#8220;single&#8221; if you prefer).<\/p>\n<p>Voila:\u00a0s-<em>cis\u00a0<\/em>and\u00a0s<em>-trans \u00a0<\/em>conformations!<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-15628\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-s-cis-and-s-trans-feres-to-the-orientation-about-a-rotatable-carbon-carbon-single-bond-d.gif\" alt=\"s cis and s trans feres to the orientation about a rotatable carbon carbon single bond d\" width=\"600\" height=\"321\" \/><\/p>\n<p>A video says a thousand words. Pay attention to the<strong> two blue hydrogens\u00a0<\/strong>of the diene below (butadiene)\u00a0and their orientation about the central C-C single (&#8220;sigma&#8221;) bond. In one conformation, they&#8217;re oriented &#8220;<em>trans<\/em>&#8221; across the C-C single bond, and in the other conformation, they&#8217;re oriented &#8220;<em>cis<\/em>&#8221; across the C-C single bond.<\/p>\n<p><iframe class=\"giphy-embed\" src=\"https:\/\/giphy.com\/embed\/RtTpJ8DOhcSoE\" width=\"480\" height=\"300\" frameborder=\"0\" allowfullscreen=\"allowfullscreen\"><\/iframe><\/p>\n<p><a href=\"https:\/\/giphy.com\/gifs\/RtTpJ8DOhcSoE\">via GIPHY<\/a><\/p>\n<p>That&#8217;s really all there is to it.<\/p>\n<h2><strong><a id=\"three\"><\/a>3. The <em>s-trans\u00a0<\/em>Conformation Is Of Lower Energy<\/strong><\/h2>\n<p>But while we&#8217;re on the topic of s-cis and s-trans for dienes, let&#8217;s look at a few more details.<\/p>\n<p>Which conformation is lower energy?<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15626\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/4-what-is-lower-energy-s-cis-or-s-trans-the-s-trans-conformation-is-lower-in-energy-than-s-cis-because-of-steric-repulsion-it-is-about-2-kcal-mol-less-stable.gif\" alt=\"what is lower energy s cis or s trans - the s trans conformation is lower in energy than s cis because of steric repulsion it is about 2 kcal mol less stable\" width=\"600\" height=\"288\" \/><\/p>\n<p>Note that in the\u00a0s-<em>cis<\/em> conformation, the &#8220;inside&#8221; hydrogens on C-1 and C-4 are in close proximity to each other. This leads to some Van Der Waals repulsion, and the result is that the s<em>-cis\u00a0<\/em>conformation is about 2.3 kcal\/mol less stable. At any one time, about 96% of butadiene is in the\u00a0s-<em>trans<\/em> conformation.<\/p>\n<h2><a id=\"four\"><\/a>4. Some Dienes Are &#8220;Locked&#8221; In The <em>s-cis<\/em> or <em>s-trans<\/em> Orientation<\/h2>\n<p>There are situations where dienes are<strong> locked<\/strong> in a \u00a0particular orientation. For example, in 1,3-cyclohexadiene and cyclopentadiene, the two pi bonds are locked in a\u00a0s-<em>cis<\/em> orientation, while the diene bottom right is locked in the s<em>-trans<\/em> orientation.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15627\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/5-some-dienes-are-locked-in-the-s-cis-conformation-such-as-cyclohexadiene-and-cyclopentadiene-and-some-dienes-are-locked-in-s-trans.gif\" alt=\"some dienes are locked in the s cis conformation such as cyclohexadiene and cyclopentadiene and some dienes are locked in s trans\" width=\"600\" height=\"171\" \/><\/p>\n<p>This will become more relevant in the next post, when we introduce the <a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/08\/30\/the-diels-alder-reaction\/\">Diels Alder reaction<\/a>.<\/p>\n<h2><strong><a id=\"five\"><\/a>5. Conformations In Amides: (<em>Z<\/em>) and (<em>E<\/em>)<\/strong><\/h2>\n<p>One final note. It&#8217;s also useful to borrow the terms for amides, which have free (if somewhat restricted) rotation about the C-N bond.<\/p>\n<p>Here, we can refer to\u00a0s-<em>E<\/em> or s-<em>Z\u00a0<\/em>conformations of the amide (see below).<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15629\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/6-dienes-are-not-the-only-functional-group-that-can-have-s-cis-and-s-trans-for-example-amides.gif\" alt=\"dienes are not the only functional group that can have s cis and s trans for example amides6-dienes are not the only functional group that can have s cis and s trans for example amides\" width=\"600\" height=\"252\" \/><\/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\/2016\/11\/03\/alkene-nomenclature-cis-and-trans-and-e-and-z\/\" class=\"\"><span>E and Z Notation For Alkenes (+ Cis\/Trans)<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2020\/05\/29\/newman-projection-of-butane-and-gauche-conformation\/\" class=\"\"><span>Newman Projection of Butane (and Gauche Conformation)<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/08\/30\/the-diels-alder-reaction\/\" class=\"\"><span>The Diels-Alder Reaction<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/09\/08\/cyclic-dienes-and-dienophiles-in-the-diels-alder-reaction\/\" class=\"\"><span>Cyclic Dienes and Dienophiles in the Diels-Alder Reaction<\/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\/2014\/03\/20\/cycloalkanes-cis-and-trans\/\" class=\"\"><span>Geometric Isomers In Small Rings: Cis And Trans Cycloalkanes<\/span><\/a><\/li><\/ul><\/div>\n<p>&nbsp;<\/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\/3536-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\/3537-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\/3538-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\/3539-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\/3540-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<hr \/>\n<h2><a id=\"references\"><\/a>(Advanced) References and Further Reading<\/h2>\n<ol>\n<li><strong>Thermodynamic Properties of Gaseous 1,3\u2010Butadiene and the Normal Butenes above 25\u00b0C Equilibria in the System 1,3\u2010Butadiene,\u00a0<i>n<\/i>\u2010Butenes, and\u00a0<i>n<\/i>\u2010Butane<br \/>\n<\/strong>J. G. Aston, G. Szasz, H. W. Woolley, F. G. Brickwedde.<br \/>\n<em>J. Chem. Phys<\/em>.\u00a0<em>14<\/em>, 67 (1946)<br \/>\n<strong>DOI:<\/strong> <a href=\"https:\/\/doi.org\/10.1063\/1.1724108\">https:\/\/doi.org\/10.1063\/1.1724108<\/a><br \/>\nOne of the earliest studies of rotational barriers in butadiene indicate that the <em>s<\/em>-trans is favored over the\u00a0<em>s<\/em>-cis by about 2.3 kcal\/mol.<\/li>\n<li><strong>Conformational studies on small molecules<\/strong><br \/>\nE. B. Wilson<br \/>\n<em>Chem. Soc. Rev.<\/em> <strong>1972<\/strong>, <em>1<\/em>, 293-318<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/pubs.rsc.org\/en\/content\/articlelanding\/1972\/cs\/cs9720100293#!divAbstract\">10.1039\/CS9720100293<\/a><br \/>\nThis review mentions that dienes such as butadiene can exist in <em>s-cis<\/em> and <em>s-trans<\/em> forms. E. B. Wilson was a prominent spectroscopist in the 20<sup>th<\/sup> century, and even though he never received a Nobel Prize, his son (K. G. Wilson) and PhD student (Dudley Herschbach) both did.<\/li>\n<li><strong>Diene Structure and Diels-Alder Reactivity<\/strong><br \/>\nClare A. Stewart<br \/>\n<em>The Journal of Organic Chemistry<\/em> <strong>1963,<\/strong> <em>28<\/em> (12), 3320-3323<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/jo01047a010\">10.1021\/jo01047a010<\/a><br \/>\nThis studies the Diels-Alder reactivity of various dienes. Most important here is that\u00a0<em>cis<\/em>-1-methylbutadiene is relatively unreactive in the Diels-Alder, since in the\u00a0<em>s<\/em>-cis conformation the methyl group &#8220;bumps&#8221; into the C-H bond of the terminal alkene.<\/li>\n<li><strong>Conformational analysis. 120. Small polyenes<\/strong><br \/>\nJulia C. Tai and Norman L. Allinger<br \/>\n<em>Journal of the American Chemical Society<\/em> <strong>1976,<\/strong> <em>98<\/em> (25), 7928-7932<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja00441a007\">10.1021\/ja00441a007<\/a><br \/>\nIt is possible to investigate the structure of molecules in detail through computational methods, and Table 1 in this paper contains the energy differences between the <em>s-<\/em>cis and <em>s-<\/em>trans forms of various dienes.<\/li>\n<li><strong>Rotational barriers and stable rotamers in 1,3-butadiene, acrolein and glyoxal<br \/>\n<\/strong>George R. De Mar\u00e9<br \/>\n<em> Mol. Struc. THEOCHEM<\/em> <strong>1984<\/strong>, <em>107<\/em>, 127-132<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/www.sciencedirect.com\/science\/article\/abs\/pii\/0166128084800470\">10.1016\/0166-1280(84)80047-0<\/a><br \/>\nAnother paper studying the rotational barriers of butadiene through computational methods. While these calculations may have required supercomputers back then, nowadays a modern laptop will be able to carry these out in minutes (or less)!<\/li>\n<li><strong>Planar s-cis-1,3-butadiene<\/strong><br \/>\nE. Squillacote, R. S. Sheridan, O. L. Chapman, and F. A. L. Anet<br \/>\n<em>Journal of the American Chemical Society<\/em> <strong>1979,<\/strong> <em>101<\/em> (13), 3657-3659<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja00507a042\">10.1021\/ja00507a042<\/a><br \/>\nThis paper reports the characterization (FT-IR) of <em>s-cis<\/em> butadiene through an unusual method \u2013 cooling the hot (400 \u2013 900 \u00b0C) vapors on a very cold (30 K) surface. By measuring the rate of disappearance of a specific band attributed to <em>s<\/em>-cis butadiene (1430 cm<sup>-1<\/sup>), the authors were able to determine the activation enthalpy for converting <em>s<\/em>-cis to <em>s<\/em>-trans butadiene to be 3.9 kcal\/mol.<\/li>\n<li><strong>Thermodynamics of conformational change in 1,3-butadiene studied by high-temperature ultraviolet absorption spectroscopy<\/strong><br \/>\nPhilip W. Mui and Ernest Grunwald<br \/>\n<em>Journal of the American Chemical Society<\/em> <strong>1982,<\/strong> <em>104<\/em> (24), 6562-6566<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/ja00388a014\">10.1021\/ja00388a014<\/a><br \/>\nIn this paper, the authors do a more rigorous experimental study of the energy difference between the s-cis and s-trans forms of butadiene and determine it to be 2.9 kcal\/mol. Prof. Grunwald did his undergraduate studies and PhD at UCLA under\u00a0 Prof. Saul Winstein, and contributed to the development of the \u2018Grunwald-Winstein equation\u2019 in solvolysis.<\/li>\n<li><strong>Le 2,3\u2010Ditertiobutylbutadi\u00e8ne<\/strong><br \/>\nJ. Backer<br \/>\n<em>Rec. Trav. Chim. Pays-Bas<\/em> <strong>1939<\/strong>, <em>58<\/em> (7), 643-661<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/onlinelibrary.wiley.com\/doi\/abs\/10.1002\/recl.19390580712\">10.1002\/recl.19390580712<\/a><br \/>\nDiels-Alder reactions of 2,3-di-t-butyl-1,3-butadiene have not been observed &#8211; the\u00a0<em>s<\/em>-cis form is far too disfavored, since it brings together two\u00a0<em>t<\/em>-butyl groups in close proximity!<\/li>\n<\/ol>\n","protected":false},"excerpt":{"rendered":"<p>&#8220;s-cis and s-trans conformations of dienes.&#8221; What does those terms mean? \u00a0The &#8220;s&#8211;cis&#8221; is a conformation where both double bonds are on the same side <\/p>\n","protected":false},"author":1,"featured_media":34097,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1163],"tags":[599,363,1206,1207],"post_folder":[],"class_list":["post-10748","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-dienes-and-mo-theory","tag-conformations-2","tag-dienes","tag-s-cis","tag-s-trans"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>s-cis and s-trans Conformations of Dienes &#8211; 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