{"id":8367,"date":"2014-06-27T08:15:01","date_gmt":"2014-06-27T12:15:01","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=8367"},"modified":"2026-05-07T05:54:19","modified_gmt":"2026-05-07T10:54:19","slug":"substituted-cyclohexanes-equatorial-vs-axial","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2014\/06\/27\/substituted-cyclohexanes-equatorial-vs-axial\/","title":{"rendered":"Substituted Cyclohexanes &#8211; Axial vs Equatorial"},"content":{"rendered":"<p><strong>Equatorial vs Axial Groups: Why The Equatorial Position Is Of Lower Energy<\/strong><\/p>\n<p>Just to bring you up to speed,\u00a0<a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/06\/06\/the-cyclohexane-chair-flip-energy-diagram\/\"> let&#8217;s quickly review the last post. <\/a>\u00a0And at the bottom, I\u2019ll also correct a little fib I made in the last article.<\/p>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-38622\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2024\/12\/0-Summary-bulky-groups-prefer-the-equatorial-position-of-cyclohexane-chair-due-to-diaxial-interactions-gauche-interactions-newman-projection-of-chair.gif\" alt=\"Summary- bulky groups prefer the equatorial position of cyclohexane chair due to diaxial interactions gauche interactions newman projection of chair\" width=\"640\" height=\"678\" \/><\/a><\/p>\n<p><strong>Table Of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">Brief Review On The Cyclohexane Chair Conformation<\/a><\/li>\n<li><a href=\"#two\">In 1-Methylcyclohexane, The Ratio Of Equatorial Methyl Conformer To Axial Methyl Conformer Is About 95:5<\/a><\/li>\n<li><a href=\"#three\">The &#8220;Equatorial Methyl&#8221; Conformation Encounters Fewer Gauche Interactions Than The &#8220;Axial Methyl&#8221; Conformation<\/a><\/li>\n<li><a href=\"#four\">The Experimentally Determined Equilibrium Ratio Of Conformers Can Be Used to Calculate The Energy Difference<\/a><\/li>\n<li><a href=\"#five\">Summary: Axial Vs Equatorial Groups<\/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><a id=\"one\"><\/a>1. Brief Review On The Cyclohexane Chair Conformation<\/h2>\n<ul>\n<li>Cyclohexane undergoes a <strong>conformational<\/strong> interconversion known as a <strong>chair flip<\/strong>. \u00a0In this <a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/05\/30\/the-cyclohexane-chair-flip\/\">chair flip<\/a>, <strong>all axial groups become equatorial<\/strong>, and <strong>all equatorial groups become axial.<\/strong> [<span style=\"color: #993366;\"><em>but all &#8220;up&#8221; groups remain up, and all &#8220;down&#8221; groups remain down<\/em><\/span>].<\/li>\n<li>The two chair forms of cyclohexane itself are completely indistinguishable, but this is <strong>not<\/strong> true in most <strong>substituted cyclohexanes<\/strong>. For example, in 1-methylcyclohexane, one chair conformer has an <strong>axial<\/strong> methyl group, and in the other the methyl group is <strong>equatorial<\/strong>. These are conformational isomers, or simply, \u201cconformers\u201d.<\/li>\n<li>At room temperature, <strong>these two conformations are in rapid equilibrium with each other<\/strong>. There is an activation barrier of about <strong>10 kcal\/mol<\/strong> for this interconversion, since the high-energy \u201chalf-chair\u201d conformer is an intermediate in this process. Trying to observe both conformations of 1-methylcyclohexane at room temperature with a device for taking \u201cmolecular snapshots\u201d <span style=\"color: #993366;\"><em>(an NMR spectrometer is what we use &#8211; more precise details on this in future posts)<\/em><\/span> results in a <em>blurred<\/em> picture. Like an old camera trying to take pictures of spokes on a moving bicycle wheel, the \u201cshutter speed\u201d is too slow, and the result is that the images blend together to give an average. Using this device, it&#8217;s simply not possible to see both cyclohexane conformers of 1-methylcyclohexane at room temperature.<\/li>\n<li><strong>At very low temperatures<\/strong> (about 80 degrees above absolute zero) <strong>equilibrium between the two chair forms stops<\/strong>, because there isn\u2019t enough thermal energy available to ascend the activation barrier of 10 kcal\/mol. Now, \u00a0when we try to take \u201cmolecular snapshots\u201d of 1-methylcyclohexane, <strong>we do indeed see the two conformations separately<\/strong>. [<a href=\"#noteone\">Note 1<\/a>]<\/li>\n<\/ul>\n<p>Now, the correction to the fib.<\/p>\n<p>In the last post, we assumed that these two conformations would be equal in energy, and therefore we would see a 50:50 mixture of the two conformations.<\/p>\n<p>Is this true? No.<\/p>\n<h2><a id=\"two\"><\/a>2. In 1-Methylcyclohexane, The Ratio of the Equatorial Methyl Conformer to the Axial Methyl Conformer Is 95:5 .<\/h2>\n<p>There&#8217;s only one way to find out. Do the experiment with a <strong>substituted<\/strong> cyclohexane such as 1-methylcyclohexane.<\/p>\n<p>When we do this, here&#8217;s what we find. Instead of being equal, the ratio of &#8220;equatorial methyl&#8221; to &#8220;axial methyl&#8221; conformers is about<strong> 95:5 \u00a0favouring the conformation where the methyl group is equatorial.\u00a0<\/strong>[<a href=\"#notetwo\">Note 2<\/a>]<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-42139\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2025\/09\/1-in-1-methylcyclohexane-ratio-of-equatorial-to-axial-methyl-is-95-5-means-that-equatorial-is-of-lower-energy.gif\" alt=\"1-in 1 methylcyclohexane ratio of equatorial to axial methyl is 95 5 means that equatorial is of lower energy\" width=\"640\" height=\"438\" \/><\/a><\/p>\n<p>Very interesting! This must mean that the <strong>equatorial conformation is of lower energy than the &#8220;axial&#8221; conformation.<\/strong><\/p>\n<p>Why might that be?<\/p>\n<h2><a id=\"three\"><\/a>3. The &#8220;Equatorial&#8221; Methyl Conformation Encounters Fewer Gauche Interactions Than the Axial Methyl Conformation<\/h2>\n<p>Let&#8217;s look at the Newman projection of the chair. Imagine looking along the C-1 to C-2 bond (which is coplanar with the C-4 to C-5 bond). Here&#8217;s what you&#8217;d see.<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-42140\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2025\/09\/2-newman-projection-of-cyclohexane-chair-of-1-methylcyclohexane-showing-gauche-interaction-dihedral-angle-60-for-axial-methyl.gif\" alt=\"newman projection of cyclohexane chair of 1 methylcyclohexane showing gauche interaction dihedral angle 60 for axial methyl\" width=\"640\" height=\"354\" \/><\/a><\/p>\n<p>Note that in the conformation where methyl is axial, \u00a0there is a <strong>gauche<\/strong> <strong>interaction<\/strong> between the axial methyl group and C-3.<\/p>\n<p>This is <strong>absent<\/strong> in the conformation where methyl is equatorial. \u00a0This gauche interaction is an example of <strong>van der Waals strain<\/strong>, which is what makes the <strong>axial<\/strong> conformer <strong>higher in energy.<\/strong><\/p>\n<p>There is actually a\u00a0<strong>second<\/strong> gauche interaction if you look along C-1 to C-6 . This gauche interaction is with C-5.<\/p>\n<p>A simple way to keep track is to think of it as the methyl group interacting with the other &#8216;axial&#8217; hydrogens, at C-3 and C-5. These are called &#8220;diaxial interactions&#8221; since they are steric interactions between axial substituents.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-42141\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2025\/09\/3-steric-interactions-in-1-methylcyclohexane-where-methyl-is-axial-diaxial-interaactions.gif\" alt=\"steric interactions in 1 methylcyclohexane where methyl is axial diaxial interaactions\" width=\"640\" height=\"283\" \/><\/a><\/p>\n<p>Bottom line: <b>in two unequal conformations of a cyclohexane ring, the conformation where steric interactions are minimized will be favoured.\u00a0<\/b> [<a href=\"#notetwo\">Note 2<\/a>]<\/p>\n<h2><a id=\"four\"><\/a>4. The Experimentally Determined Equilibrium Ratio Of Conformers Can Be Used To Calculate The Energy Difference<\/h2>\n<p>Now here&#8217;s a neat consequence of this knowledge. Since this ratio of conformers (95:5) represents a system at equilibrium, we can actually use it to calculate the\u00a0<strong>difference in energy<\/strong> of these two conformers using the following equation:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-42142\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2025\/09\/4-arrhenius-equation-shows-relationship-between-equiibrium-constant-and-activation-energy.gif\" alt=\"arrhenius equation shows relationship between equiibrium constant and activation energy\" width=\"640\" height=\"356\" \/><\/a><\/p>\n<p>For a 50:50 mixture (<em>K<\/em> = 1) the energy difference\u00a0\u0394G would be zero.<\/p>\n<p>For methylcyclohexane at room temperature (298 K) the 95:5 ratio of equatorial to axial conformers translates to an energy difference of\u00a0<strong>1.74 kcal\/mol.\u00a0<\/strong><\/p>\n<p>In other words, <strong>the equatorial conformer is more stable by 1.74 kcal\/mol.<\/strong><\/p>\n<p>Since there are two gauche interactions, and the strain energy is 1.74 kcal\/mol, it&#8217;s easy to calculate the value of each interaction: 0.87 kcal\/mol .<\/p>\n<h2><a id=\"five\"><\/a>5. Summary: Axial Vs Equatorial Groups<\/h2>\n<p>Now this opens up all kinds of questions. If a methyl group (CH<sub>3<\/sub>) leads to an energy difference of 1.70 kcal\/mol, then what effect would an ethyl group (CH<sub>2<\/sub>CH<sub>3<\/sub>) have? Or a Cl? Or OH ? Or <em>tert<\/em>-butyl ?<\/p>\n<p>We can use the same approach to measure all of these numbers. More about that in the next post.<\/p>\n<p>Next Post: <a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/07\/01\/substituted-cyclohexanes-a-values\/\">Substituted Cyclohexanes: A-Values<\/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\/2014\/07\/01\/substituted-cyclohexanes-a-values\/\" class=\"\"><span>Ranking The Bulkiness Of Substituents On Cyclohexanes: \u201cA-Values\u201d<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/07\/23\/which-cyclohexane-chair-is-of-lower-energy\/\" class=\"\"><span>Cyclohexane Chair Conformation Stability: Which One Is Lower Energy?<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/08\/05\/fused-rings\/\" class=\"\"><span>Fused Rings \u2013 Cis-Decalin and Trans-Decalin<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/08\/14\/bridged-bicyclic-compounds-and-how-to-name-them\/\" class=\"\"><span>Naming Bicyclic Compounds \u2013 Fused, Bridged, and Spiro<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/09\/02\/bredts-rule-and-summary-of-cycloalkanes\/\" class=\"\"><span>Bredt\u2019s Rule (And Summary of Cycloalkanes)<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/organic-chemistry-practice-problems\/cycloalkanes-practice-problems\/\" class=\"\"><span>Cycloalkanes Practice Problems (MOC Membership)<\/span><\/a><\/li><\/ul><\/div>\n<p><strong><a id=\"noteone\"><\/a>Note 1. <\/strong>\u00a0This is a bit of a cheat. In the equation \u00a0\u0394G = \u2013RT ln <em>K<\/em> \u00a0, the value of K is related to T, so the equilibrium ratio at \u201380 \u00b0C will be a bit different than the value at room temperature.\u00a0 However, one can then solve for \u0394G and use this number to calculate what K is at room temperature.<\/p>\n<p><strong><a id=\"notetwo\"><\/a>Note 2. <\/strong>Enterprising students might ask what happens if the axial hydrogens on C-3 and C-5 are removed. Would this change the equilibrium? Absolutely!<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-42143\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2025\/09\/F1-diagram-of-dioxolane-whos-that-there-are-no-diaxial-interactions-since-the-oxygens-occupy-the-place-of-the-carbons.gif\" alt=\"diagram of dioxolane whos that there are no diaxial interactions since the oxygens occupy the place of the carbons\" width=\"640\" height=\"315\" \/><\/a><\/p>\n<p>In the molecule above, the CH<sub>2<\/sub> groups at C-3 and C-5 have been replaced by oxygen. Since there are no longer any significant diaxial interactions between the methyl group and substitutents on the ring, there is no significant energy difference between the equatorial and axial conformations of this molecule.<\/p>\n<hr \/>\n<h2><a id=\"quizzes\"><\/a>Quiz Yourself!<\/h2>\n<p><br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/1116-Front-Image-Only.png\" alt=\"\" width=\"600\" height=\"450\" \/><\/a><\/p>\n<p style=\"text-align: center;\"><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a MOC member<\/strong><\/a> to see the clickable quiz with answers on the back.<\/p>\n<p><br \/>\n<br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/1117-Front-Image-Only.png\" alt=\"\" width=\"600\" height=\"450\" \/><\/a><\/p>\n<p style=\"text-align: center;\"><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a MOC member<\/strong><\/a> to see the clickable quiz with answers on the back.<\/p>\n<p><br \/>\n<br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/1118-Front-Image-Only.png\" alt=\"\" width=\"600\" height=\"450\" \/><\/a><\/p>\n<p style=\"text-align: center;\"><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a MOC member<\/strong><\/a> to see the clickable quiz with answers on the back.<\/p>\n<p><br \/>\n<br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/1120-Front-Image-Only.png\" alt=\"\" width=\"600\" height=\"450\" \/><\/a><\/p>\n<p style=\"text-align: center;\"><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a MOC member<\/strong><\/a> to see the clickable quiz with answers on the back.<\/p>\n<p><br \/>\n<br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/1122-Front-Image-Only.png\" alt=\"\" width=\"600\" height=\"450\" \/><\/a><\/p>\n<p style=\"text-align: center;\"><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a MOC member<\/strong><\/a> to see the clickable quiz with answers on the back.<\/p>\n<p><br \/>\n<br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/1119-Front-Image-Only.png\" alt=\"\" width=\"600\" height=\"450\" \/><\/a><\/p>\n<p style=\"text-align: center;\"><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a MOC member<\/strong><\/a> to see the clickable quiz with answers on the back.<\/p>\n<p><\/p>\n<hr \/>\n<h2><a id=\"references\"><\/a>(Advanced) References and Further Reading<\/h2>\n<p>This is a topic commonly taught to undergraduates in Organic Chemistry, and goes along with the discussion on <em>A-<\/em>values. Substituents in cyclohexane can take two positions, axial and equatorial, and the <em>preferred<\/em> conformation is dictated by stereoelectronic effects.<\/p>\n<ol>\n<li><strong>Electron Diffraction Investigations of Molecular Structures. II. Results Obtained by the Rotating Sector Method.<br \/>\n<\/strong>Hassel, O.; Viervoll, H.<strong><br \/>\n<\/strong><em>Acta Chem. Scand.<\/em><strong> 1947<\/strong>,<em> 1<\/em>, 149-168<strong><br \/>\nDOI: <\/strong><a href=\"http:\/\/actachemscand.org\/doi\/10.3891\/acta.chem.scand.01-0149\">3891\/acta.chem.scand.01-0149<\/a><\/li>\n<li><strong>The Structure of Molecules Containing Cyclohexane or Pyranose Rings.<br \/>\n<\/strong>Hassel, O.; Ottar, B.<strong><br \/>\n<\/strong><em>Acta Chem. Scand.<\/em><strong> 1947<\/strong>, <em>1<\/em>, 929-943<strong><br \/>\nDOI: <\/strong><a href=\"http:\/\/actachemscand.org\/doi\/10.3891\/acta.chem.scand.01-0929\">3891\/acta.chem.scand.01-0929<\/a><br \/>\nOdd Hassel first confirmed that cyclohexane exists in the now commonly accepted <em>chair<\/em> confirmation. He also proposed that substituents can take two different types of positions on the ring, which he called c- and e-bonds. He also showed that the conformational analysis of cyclohexanes can be extended to other unsaturated 6-membered rings, such as the pyranoses commonly found in carbohydrates. Odd Hassel later shared the Nobel Prize in Chemistry with Prof. D. H. R. Barton for his work on conformational analysis.<\/li>\n<li><strong>The Thermodynamic Properties and Molecular Structure of Cyclohexane, Methylcyclohexane, Ethylcyclohexane and the Seven Dimethylcyclohexanes<br \/>\n<\/strong>Charles W. Beckett, Kenneth S. Pitzer, and Ralph Spitzer<strong><br \/>\n<\/strong><em>Journal of the American Chemical Society<\/em><strong> 1947<\/strong>, <em>69<\/em> (10), 2488-2495<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja01202a070\">1021\/ja01202a070<\/a><br \/>\nThis paper first proposes the terms \u2018polar\u2019 and \u2018equatorial\u2019 for the two types of positions substituents can take in cyclohexane.<\/li>\n<li><strong>Nomenclature of <em>cyclo<\/em>Hexane Bonds<br \/>\n<\/strong>BARTON, D., HASSEL, O., PITZER, K., PRELOG, V.<br \/>\n<em>Nature<\/em><strong> 1953<\/strong>, <em>172<\/em>, 1096\u20131097<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/www.nature.com\/articles\/1721096b0\">1038\/1721096b0<\/a><\/li>\n<li><strong>Nomenclature of Cyclohexane Bonds<\/strong><br \/>\nH. R. Barton, O. Hassel, K. S. Pitzer, V. Prelog<br \/>\n<em>Science<\/em> <strong>1954<\/strong>, 119, 49<br \/>\n<strong>DOI<\/strong>:<a href=\"https:\/\/science.sciencemag.org\/content\/119\/3079\/49\/tab-article-info\"> 10.1126\/science.119.3079.49<\/a><br \/>\nThese are the first instances of the terms \u2018axial\u2019 and \u2018equatorial\u2019 being used to denote the two positions substituents can take in cyclohexane. This was also back in the day when scientists could safely cross-publish to get better visibility \u2013 pretty much the same article is published in both <em>Science<\/em> and <em>Nature<\/em>, considered top journals.<\/li>\n<li><strong>Neighboring Carbon and Hydrogen. XIX. t-Butylcyclohexyl Derivatives. Quantitative Conformational Analysis<br \/>\n<\/strong>S. Winstein and N. J. Holness<strong><br \/>\n<\/strong><em>Journal of the American Chemical Society<\/em><strong> 1955<\/strong>, <em>77<\/em> (21), 5562-5578<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja01626a037?journalCode=jacsat&amp;quickLinkVolume=77&amp;quickLinkPage=5562&amp;selectedTab=citation&amp;volume=77\">10.1021\/ja01626a037<\/a><br \/>\nThis is the paper that first introduced the concept of <em>A<\/em>-values (see Table XII) and how to determine them through kinetic (solvolytic) measurements, which is what Prof. Winstein was well known for. The introduction features a summary of how <em>A<\/em>-values are determined, and later on, Prof. Winstein states \u201c<em>The energy quantity by which a t-butyl group favors the equatorial position is sufficiently large to guarantee conformational homogeneity to most 4-t-butylcyclohexyl derivatives<\/em>\u201d<em>, <\/em>which is commonly taught in organic chemistry classes today.<\/li>\n<li><strong>STUDIES OF RATES OF CONVERSION AND POPULATIONS OF VARIOUS CONFORMATIONS OF SATURATED RING COMPOUNDS BY N.M.R.: I. CHLOROCYCLOHEXANE AND BROMOCYCLOHEXANE<br \/>\n<\/strong> W. Reeves, K. O. Str\u00f8mme<strong><br \/>\n<\/strong><em>Canadian Journal of Chemistry<\/em>, <strong>1960<\/strong>, <em>38 <\/em>(8): 1241-1248<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/www.nrcresearchpress.com\/doi\/abs\/10.1139\/v60-176#.Xym9GxNKh24\">10.1139\/v60-176<\/a><br \/>\nThis might be the first paper to actually use NMR to determine axial:equatorial ratios of substituted cyclohexanes. However, the authors do not explicitly calculate <em>A<\/em>-values here, which is why this paper is less well-known compared to the <em>JACS<\/em> publication of Jensen, Bushweller, and Beck below.<\/li>\n<li><strong>Conformational Analysis\u2010The Fundamental Contributions of D. H. R. Barton and O. Hassel<br \/>\n<\/strong><em>Topics in Stereochemistry<\/em><strong> 1967<\/strong>, <em>1<\/em>, 1-17<br \/>\n<strong>DOI<\/strong>:<a href=\"https:\/\/onlinelibrary.wiley.com\/doi\/abs\/10.1002\/9780470147153.ch1\"> 10.1002\/9780470147153.ch1<\/a><br \/>\nA summary of the key papers that Profs. Barton and Hassel published in confirmation analysis, earning them the Nobel Prize in Chemistry in 1969.<\/li>\n<li><strong>Conformational preferences in monosubstituted cyclohexanes determined by nuclear magnetic resonance spectroscopy<br \/>\n<\/strong>Frederick R. Jensen, C. Hackett Bushweller, and Barbara H. Beck<strong><br \/>\n<\/strong><em>Journal of the American Chemical Society <\/em><strong>1969,<\/strong><em> 91 <\/em>(2), 344-351<em><br \/>\n<\/em><strong>DOI<\/strong>: <a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja01030a023\">10.1021\/ja01030a023<\/a><br \/>\nThis is the first paper to actually determine A-values through NMR, by measuring the equatorial:axial ratio of various monosubstituted cyclohexanes.<\/li>\n<li><strong>The experimental determination of the conformational free energy, enthalpy, and entropy differences for alkyl groups in alkylcyclohexanes by low temperature carbon-13 magnetic resonance spectroscopy<\/strong><br \/>\nHarold Booth and Jeremy R. Everett<br \/>\n<em>J. Chem. Soc., Perkin Trans. 2,<\/em><strong> 1980<\/strong>, 255-259<strong><br \/>\nDOI<\/strong>: <a href=\"https:\/\/pubs.rsc.org\/en\/content\/articlelanding\/1980\/P2\/P29800000255#!divAbstract\">10.1039\/P29800000255<\/a><strong><br \/>\n<\/strong>This paper covers the use of <sup>13<\/sup>C NMR to determine the free energy differences between axial- and equatorial-subtituted alkylcyclohexanes (in essence, <em>A<\/em>-values).<\/li>\n<\/ol>\n","protected":false},"excerpt":{"rendered":"<p>Equatorial vs Axial Groups: Why The Equatorial Position Is Of Lower Energy Just to bring you up to speed,\u00a0 let&#8217;s quickly review the last post. <\/p>\n","protected":false},"author":1,"featured_media":38622,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1409],"tags":[1001,992,965,999,993,513,1002,994,1000],"post_folder":[],"class_list":["post-8367","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-conformations-cycloalkanes","tag-a-value","tag-axial","tag-cycloalkanes","tag-diaxial","tag-equatorial","tag-equilibrium","tag-gauche","tag-newman","tag-sterics"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Substituted Cyclohexanes: Axial vs Equatorial &#8211; Master Organic Chemistry<\/title>\n<meta name=\"description\" content=\"Why is the equatorial vs axial position favored? 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