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<!DOCTYPE html PUBLIC "-//W3C//DTD XHTML 1.0 Transitional//EN" "http://www.w3.org/TR/xhtml1/DTD/xhtml1-transitional.dtd"> <html xmlns="http://www.w3.org/1999/xhtml"> <head profile="http://gmpg.org/xfn/1"> <title>Computational Organic Chemistry » 2014 » August</title> <meta name="google-site-verification" content="g1Myv4tUVAmqRbwZeBi7IPuSZpP64RWjVJ6itIoouCo"> <meta http-equiv="Content-Type" content="text/html; charset=UTF-8"> <style type="text/css" media="screen">@import url( /blog/wp-content/themes/comporg/style.css);</style> <link rel="stylesheet" id="wp-block-library-css" href="/blog/wp-includes/css/dist/block-library/style.min.css?ver=5.6.1" type="text/css" media="all"> <script type="text/javascript">  </script> </head> <body> <div id="header"> <div id="header_img"></div> </div> <div id="link_section"> <div style="float:left"> <a href="/blog/about">About this Blog</a> | <a href="/">Book Homepage</a> | <a href="http://www.wiley.com/WileyCDA/WileyTitle/productCd-0471713422.html">Purchase the Book</a> </div> </div> <div id="after_links"></div> <div id="content"> <div id="main"> <h2 class="post-title">Archive for August, 2014</h2> <div class="box"> <h2><a href="/blog/archives/3213" rel="bookmark" title="Permanent Link: A pentacoordinate carbon">A pentacoordinate carbon</a></h2> <div class="post-content"> <p>Trying to get carbon to bond in unnatural ways seems to be a passion for many organic chemists! Schleyer has been interested in unusual carbon structures for decades and he and Schaefer now report a molecule with a pentacoordinate carbon bound to five other carbon atoms. Their proposed target is pentamethylmethane cation C(CH<sub>3</sub>)<sub>5</sub><sup>+</sup> <b>1</b>.<a href="#CMe5"><sup>1</sup></a> The optimized geometry of <b>1</b>, which has <i>C<sub>3h</sub></i> symmetry, at MP2/cc-pVTZ is shown in Figure 1. The bonds from the central carbon to the equatorial carbon are a rather long 1.612 Å, but the bonds to the axial carbon are even longer, namely 1.736 Å. Bader analysis shows five bond critical points, each connecting the central carbon to one of the methyl carbons. Wiberg bond index and MO analysis suggests that the central carbon is tetravalent, with a 2-electron-3-center bond involving the central and axial carbons.</p> <table align="center" border="0" cellspacing="0" cellpadding="4"> <tr align="center"> <td colspan="2"> <p></p> <div class="jmol" id="CMe5"> <a onclick="return false"><br> <img src="/blog/wp-content/CMe5.jpg" onclick="insertJmol('CMe5',300,300,'CMe5.xyz')"></a> </div> <p><b>1</b></p> </td> </tr> <tr align="center"> <td> <p></p> <div class="jmol" id="CMe5ts1"> <a onclick="return false"><br> <img src="/blog/wp-content/CMe5ts1.jpg" onclick="insertJmol('CMe5ts1',300,300,'CMe5ts1.xyz')"></a> </div> <p><b>TS1</b></p> </td> <td> <p></p> <div class="jmol" id="CMe5ts2"> <a onclick="return false"><br> <img src="/blog/wp-content/CMe5ts2.jpg" onclick="insertJmol('CMe5ts2',300,300,'CMe5ts2.xyz')"></a> </div> <p><b>TS2</b></p> </td> </tr> </table> <p align="center"><b>Figure 1</b>. MP2/cc-pVTZ optimized geometries of <b>1</b> and dissociation transition states.</p> <p>So while <b>1</b> is a local energy minimum, it sits in a very shallow well. One computed dissociation path, which passes through <b>TS1</b> (Figure 1) on its way to 2-methyl-butyl cation and methane has a barrier of only 1.65 kcal mol<sup>-1</sup> (CCSD(T)/CBS + ZPE). A second dissociation pathway goes through <b>TS2</b> to t-butyl cation and ethane with a barrier of only 1.34 kcal mol<sup>-1</sup>. Worse still is that the free energy estimates suggest “spontaneous dissociation … through both pathways”.</p> <p>Undoubtedly, this will not be the last word on trying to torture a poor carbon atom.</p> <h3>References</h3> <p><a name="CMe5"></a></p> <p>(1) McKee, W. C.; Agarwal, J.; Schaefer, H. F.; Schleyer, P. v. R. "Covalent Hypercoordination: Can Carbon Bind Five Methyl Ligands?," <i>Angew. Chem. Int. Ed.</i> <b>2014</b>, <i>53</i>, 7875-7878, DOI: <a href="http://dx.doi.org/10.1002/anie.201403314">10.1002/anie.201403314</a>.</p> <h3>InChIs</h3> <p><b>1</b>: InChI=1S/C6H15/c1-6(2,3,4)5/h1-5H3/q+1<br>InChIKey=GGCBGJZCTGZYFV-UHFFFAOYSA-N</p>  </div> <p class="bottom"> <span class="cat"><a href="/blog/archives/category/authors/schaefer" rel="category tag">Schaefer</a> &<a href="/blog/archives/category/authors/schleyer" rel="category tag">Schleyer</a></span> <span class="user">Steven Bachrach</span> <span class="date">25 Aug 2014</span> <span class="comments"><a href="/blog/archives/3213#comments">1 Comment</a></span> </p> </div> <div class="box"> <h2><a href="/blog/archives/3193" rel="bookmark" title="Permanent Link: Torqoselectivity in forming a Cis,Trans-Cyclooctadienone">Torqoselectivity in forming a Cis,Trans-Cyclooctadienone</a></h2> <div class="post-content"> <p>Houk’s theory of torquoselectivity is a great achievement of computational chemistry, as told in Chapter 4.6 of the second edition of my book. Houk, in a collaboration with Krenske and Hsung, now report on an application of torquoselectivity in the formation of a <i>cis-trans</i>-cyclooctadienone intermediate.<a href="#torqOct1"><sup>1</sup></a></p> <p>The proposed reaction is shown in Scheme 1, where the bicyclic compound undergoes a conrotatory ring opening in just one orientation to form the <i>E,E</i>-cyclooctadienone, which can then ring close to product.</p> <p align="center"><b>Scheme 1.</b><br><img src="/blog/wp-content/torqOctImg.png"></p> <p>Houk ran M06-2x//6-311+G(d,p)//B3LYP/6-31G(d) computations on the model system <b>1</b>, passing over the two torquodistinctive transition states <b>TSEE</b> and <b>TSZZ</b>, and on to produce the two cyclooctadienones <b>2EE</b> and <b>2ZZ</b>, respectively. As seen in Figure 1, the barrier through <b>TSEE</b> is favored by 9.8 kcal mol<sup>-1</sup>, and leads to the much more favorable cycloocatadienone <b>2EE</b>.</p> <table align="center" border="0" cellspacing="0" cellpadding="3"> <tr align="center"> <td colspan="2"> <p></p> <div class="jmol" id="torqOct1"> <a onclick="return false"><br> <img src="/blog/wp-content/torqOct1.jpg" onclick="insertJmol('torqOct1',300,300,'torqOct1.xyz')"></a> </div> <p><b>1</b><br>0.0</p> </td> </tr> <tr align="center"> <td> <p></p> <div class="jmol" id="torqOctTSEE"> <a onclick="return false"><br> <img src="/blog/wp-content/torqOctTSEE.jpg" onclick="insertJmol('torqOctTSEE',300,300,'torqOctTSEE.xyz')"></a> </div> <p><b>TSEE</b><br>32.3</p> </td> <td> <p></p> <div class="jmol" id="torqOct2EE"> <a onclick="return false"><br> <img src="/blog/wp-content/torqOct2EE.jpg" onclick="insertJmol('torqOct2EE',300,300,'torqOct2EE.xyz')"></a> </div> <p><b>2EE</b><br>9.4</p> </td> </tr> <tr align="center" valign="bottom"> <td> <p></p> <div class="jmol" id="torqOctTSZZ"> <a onclick="return false"><br> <img src="/blog/wp-content/torqOctTSZZ.jpg" onclick="insertJmol('torqOctTSZZ',300,300,'torqOctTSZZ.xyz')"></a> </div> <p><b>TSZZ</b><br>42.1</p> </td> <td> <p></p> <div class="jmol" id="torqOct2ZZ"> <a onclick="return false"><br> <img src="/blog/wp-content/torqOct2ZZ.jpg" onclick="insertJmol('torqOct2ZZ',300,300,'torqOct2ZZ.xyz')"></a> </div> <p><b>2ZZ</b><br>21.0</p> </td> </tr> <tr align="center"> <td colspan="2"> <p></p> <div class="jmol" id="torqOctTS2"> <a onclick="return false"><br> <img src="/blog/wp-content/torqOctTS2.jpg" onclick="insertJmol('torqOctTS2',300,300,'torqOctTS2.xyz')"></a> </div> <p><b>TS2</b><br>47.5</p> </td> </tr> </table> <p align="center"><b>Figure 1</b>. B3LYP/6-31G(d) optimized structures and relative free energies (kcal mol<sup>-1</sup>) at M06-2x//6-311+G(d,p)//B3LYP/6-31G(d).</p> <p>Ring closure taking <b>TSEE</b> to product goes through <b>TS2</b> (Figure 1), with a very high barrier, 47.5 kcal mol<sup>-1</sup> above reactant, suggesting that this path is not likely to occur. Instead, they propose that <b>2EE</b> is first protonated (<b>2EEH<sup>+</sup></b>) and then cyclizes through <b>TS2H<sup>+ </sup></b>(Figure 2). This barrier is only 6.2 kcal mol<sup>-1</sup>, some 44 kcal mol<sup>-1</sup> lower than the neutral process through <b>TS2</b>.</p> <table align="center" border="0" cellspacing="0" cellpadding="3"> <tr align="center"> <td> <p></p> <div class="jmol" id="torqOct2EEH"> <a onclick="return false"><br> <img src="/blog/wp-content/torqOct2EEH.jpg" onclick="insertJmol('torqOct2EEH',300,300,'torqOct2EEH.xyz')"></a> </div> <p><b>2EEH<sup>+</sup></b></p> </td> <td> <p></p> <div class="jmol" id="torqOctTS2H"> <a onclick="return false"><br> <img src="/blog/wp-content/torqOctTS2H.jpg" onclick="insertJmol('torqOctTS2H',300,300,'torqOctTS2H.xyz')"></a> </div> <p><b>TS2H<sup>+</sup></b></p> </td> </tr> </table> <p align="center"><b>Figure 2</b>. B3LYP/6-31G(d) optimized structures</p> <h3>References</h3> <p><a name="torqOct1"></a></p> <p>(1) Wang, X.-N.; Krenske, E. H.; Johnston, R. C.; Houk, K. N.; Hsung, R. P. "Torquoselective Ring Opening of Fused Cyclobutenamides: Evidence for a Cis,Trans-Cyclooctadienone Intermediate," <i>J. Am. Chem. Soc.</i> <b>2014</b>, <i>136</i>, 9802-9805, DOI: <a href="http://dx.doi.org/10.1021/ja502252t">10.1021/ja502252t</a>.</p>  </div> <p class="bottom"> <span class="cat"><a href="/blog/archives/category/authors/houk" rel="category tag">Houk</a></span> <span class="user">Steven Bachrach</span> <span class="date">11 Aug 2014</span> <span class="comments"><a href="/blog/archives/3193#respond">No Comments</a></span> </p> </div> <div class="box"> <h2><a href="/blog/archives/3177" rel="bookmark" title="Permanent Link: Splitting CO<sub>2</sub> with a two-coordinate boron cation">Splitting CO<sub>2</sub> with a two-coordinate boron cation</a></h2> <div class="post-content"> <p>This paper is a bit afield from the usual material I cover but this is an interesting reaction. Shoji and coworkers have prepared the two-coordinate boron species <b>1</b>,<a href="#Mes2Br"><sup>1</sup></a> and confirmed its geometry by an x-ray crystal structure. What I find interesting is its reaction with CO<sub>2</sub>, which gives <b>2</b> and organoboranes that are not identified, though presumably derived from <b>3</b>.</p> <p align="center"><img src="/blog/wp-content/Mes2B_img.png"></p> <p>M06-2x/6-311+G(d,p) computations support a hypothetical mechanism whereby first a complex between <b>1</b> and CO<sub>2</sub> is formed (<b>CP1</b>), that is 4.4 kcal mol<sup>-1</sup> above isolated reactants. Then passing through <b>TS1</b>, which is 4.2 kcal mol<sup>-1</sup> above <b>CP1</b>, an intermediate is formed (<b>INT</b>), which is almost 6 kcal mol<sup>-1</sup> below starting materials. A second transition state is then traversed (about 1 kcal mol<sup>-1</sup> below starting materials), to form an exit complex between <b>2</b> and <b>3</b>, which can then separate to the final products with an overall exothermicity of 10.6 kcal mol<sup>-1</sup>. The structures of these critical points are shown in Figure 1.</p> <table align="center" border="0" cellspacing="0" cellpadding="3"> <tr align="center"> <td> <p></p> <div class="jmol" id="Mes2B_R"> <a onclick="return false"><br> <img src="/blog/wp-content/Mes2B_R.jpg" onclick="insertJmol('Mes2B_R',300,300,'Mes2B_R.xyz')"></a> </div> <p><b>1</b><br>(0.0)</p> </td> <td> <p></p> <div class="jmol" id="Mes2B_CP1"> <a onclick="return false"><br> <img src="/blog/wp-content/Mes2B_CP1.jpg" onclick="insertJmol('Mes2B_CP1',300,300,'Mes2B_CP1.xyz')"></a> </div> <p><b>CP1</b><br>(4.4)</p> </td> </tr> <tr align="center"> <td> <p></p> <div class="jmol" id="Mes2B_TS1"> <a onclick="return false"><br> <img src="/blog/wp-content/Mes2B_TS1.jpg" onclick="insertJmol('Mes2B_TS1',300,300,'Mes2B_TS1.xyz')"></a> </div> <p><b>TS1</b><br>(8.6)</p> </td> <td> <p></p> <div class="jmol" id="Mes2B_INT"> <a onclick="return false"><br> <img src="/blog/wp-content/Mes2B_INT.jpg" onclick="insertJmol('Mes2B_INT',300,300,'Mes2B_INT.xyz')"></a> </div> <p><b>INT</b><br>(-5.7)</p> </td> </tr> <tr align="center"> <td> <p></p> <div class="jmol" id="Mes2B_TS2"> <a onclick="return false"><br> <img src="/blog/wp-content/Mes2B_TS2.jpg" onclick="insertJmol('Mes2B_TS2',300,300,'Mes2B_TS2.xyz')"></a> </div> <p><b>TS2</b><br>(-1.1)</p> </td> <td> <p></p> <div class="jmol" id="Mes2B_CP2"> <a onclick="return false"><br> <img src="/blog/wp-content/Mes2B_CP2.jpg" onclick="insertJmol('Mes2B_CP2',300,300,'Mes2B_CP2.xyz')"></a> </div> <p><b>CP2</b><br>(-9.0)</p> </td> </tr> </table> <p align="center"><b>Figure 1</b>. M06-2x/6-311+G(d,p) optimized structures. Relative energy in kcal mol<sup>-1</sup>.</p> <h3>References</h3> <p><a href="#Mes2Br"></a></p> <p>(1) Shoji, Y.; Tanaka, N.; Mikami, K.; Uchiyama, M.; Fukushima, T. "A two-coordinate boron cation featuring C–B<sup>+</sup>–C bonding," <i>Nat. Chem.</i> <b>2014</b>, <i>6</i>, 498-503, DOI: <a href="http://dx.doi.org/10.1038/nchem.1948">10.1038/nchem.1948</a>.</p> <h3>InChIs</h3> <p><b>1</b>: InChI=1S/C18H22B/c1-11-7-13(3)17(14(4)8-11)19-18-15(5)9-12(2)10-16(18)6/h7-10H,1-6H3/q+1<br>InChIKey=WLUJABFTLHAEMI-UHFFFAOYSA-N</p> <p><b>2</b>: InChI=1S/C10H11O/c1-7-4-8(2)10(6-11)9(3)5-7/h4-5H,1-3H3/q+1<br>InChIKey=CUJVTHUIQVMVHD-UHFFFAOYSA-N</p> <p><b>3</b>: InChI=1S/C9H11BO/c1-6-4-7(2)9(10-11)8(3)5-6/h4-5H,1-3H3<br>InChIKey=ZJKBFARYTPYYGV-UHFFFAOYSA-N</p>  </div> <p class="bottom"> <span class="cat"><a href="/blog/archives/category/uncategorized" rel="category tag">Uncategorized</a></span> <span class="user">Steven Bachrach</span> <span class="date">04 Aug 2014</span> <span class="comments"><a href="/blog/archives/3177#comments">1 Comment</a></span> </p> </div> <p align="center"></p> </div> <div id="sidebar"> <ul> <li class="box"> <h2> Categories </h2> <ul> <li class="cat-item cat-item-25"> <a 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href="/blog/archives/category/molecules/non-classical">non-classical</a> (4) </li> <li class="cat-item cat-item-34"> <a href="/blog/archives/category/molecules/norbornyl-cation">norbornyl cation</a> (2) </li> <li class="cat-item cat-item-49"> <a href="/blog/archives/category/molecules/nucleic-acids">nucleic acids</a> (4) </li> <li class="cat-item cat-item-36"> <a href="/blog/archives/category/molecules/oximes">oximes</a> (1) </li> <li class="cat-item cat-item-75"> <a href="/blog/archives/category/molecules/phenyloxenium">phenyloxenium</a> (1) </li> <li class="cat-item cat-item-8"> <a href="/blog/archives/category/molecules/polycyclic-aromatics">polycyclic aromatics</a> (7) </li> <li class="cat-item cat-item-50"> <a href="/blog/archives/category/molecules/propellane">propellane</a> (2) </li> <li class="cat-item cat-item-79"> <a href="/blog/archives/category/molecules/stilbene">stilbene</a> (1) </li> <li class="cat-item cat-item-80"> <a href="/blog/archives/category/molecules/sugars">sugars</a> (5) </li> <li class="cat-item cat-item-85"> <a href="/blog/archives/category/molecules/terpenes">terpenes</a> (2) </li> <li class="cat-item cat-item-89"> <a href="/blog/archives/category/molecules/twistane">twistane</a> (1) </li> </ul> </li> <li class="cat-item cat-item-22"> <a href="/blog/archives/category/nmr">NMR</a> (40) </li> <li class="cat-item cat-item-31"> <a href="/blog/archives/category/optical-rotation">Optical Rotation</a> (16) </li> <li class="cat-item cat-item-28"> <a href="/blog/archives/category/qm-method">QM Method</a> (96) <ul class="children"> <li class="cat-item cat-item-20"> <a href="/blog/archives/category/qm-method/caspt2">CASPT2</a> (1) </li> <li class="cat-item cat-item-7"> <a href="/blog/archives/category/qm-method/dft">DFT</a> (71) </li> <li class="cat-item cat-item-45"> <a href="/blog/archives/category/qm-method/focal-point">focal point</a> (7) </li> <li class="cat-item cat-item-14"> <a href="/blog/archives/category/qm-method/g3">G3</a> (3) </li> <li class="cat-item cat-item-60"> <a href="/blog/archives/category/qm-method/mp">MP</a> (11) </li> </ul> </li> <li class="cat-item cat-item-56"> <a href="/blog/archives/category/reactions">Reactions</a> (83) <ul class="children"> <li class="cat-item cat-item-13"> <a href="/blog/archives/category/reactions/12-addition">1,2-addition</a> (1) </li> <li class="cat-item cat-item-35"> <a href="/blog/archives/category/reactions/aldol">aldol</a> (4) </li> <li class="cat-item cat-item-32"> <a href="/blog/archives/category/reactions/bergman-cyclization">Bergman cyclization</a> (6) </li> <li class="cat-item cat-item-44"> <a href="/blog/archives/category/reactions/claisen-rearrangement">Claisen rearrangement</a> (2) </li> <li class="cat-item cat-item-10"> <a href="/blog/archives/category/reactions/cope-rearrangement">Cope Rearrangement</a> (5) </li> <li class="cat-item cat-item-69"> <a href="/blog/archives/category/reactions/cycloadditions">cycloadditions</a> (12) </li> <li class="cat-item cat-item-23"> <a href="/blog/archives/category/reactions/diels-alder">Diels-Alder</a> (26) </li> <li class="cat-item cat-item-47"> <a href="/blog/archives/category/reactions/electrocyclization">electrocyclization</a> (11) </li> <li class="cat-item cat-item-76"> <a href="/blog/archives/category/reactions/electrophilic-aromatic-substitution">electrophilic aromatic substitution</a> (1) </li> <li class="cat-item cat-item-5"> <a href="/blog/archives/category/reactions/ene-reaction">ene reaction</a> (1) </li> <li class="cat-item cat-item-52"> <a href="/blog/archives/category/reactions/hajos-parrish-reaction">Hajos-Parrish Reaction</a> (1) </li> <li class="cat-item cat-item-61"> <a href="/blog/archives/category/reactions/mannich">Mannich</a> (2) </li> <li class="cat-item cat-item-64"> <a href="/blog/archives/category/reactions/michael-addition">Michael addition</a> (5) </li> <li class="cat-item cat-item-40"> <a href="/blog/archives/category/reactions/ozonolysis">ozonolysis</a> (1) </li> <li class="cat-item cat-item-43"> <a href="/blog/archives/category/reactions/proton-transfer">proton transfer</a> (1) </li> <li class="cat-item cat-item-38"> <a href="/blog/archives/category/reactions/pseudopericyclic">pseudopericyclic</a> (4) </li> <li class="cat-item cat-item-63"> <a href="/blog/archives/category/reactions/strecker">Strecker</a> (1) </li> <li class="cat-item cat-item-24"> <a href="/blog/archives/category/reactions/substitution">Substitution</a> (6) </li> <li class="cat-item cat-item-93"> <a href="/blog/archives/category/reactions/wittig">Wittig</a> (1) </li> </ul> </li> <li class="cat-item cat-item-87"> <a href="/blog/archives/category/second-edition">Second Edition</a> (3) </li> <li class="cat-item cat-item-11"> <a href="/blog/archives/category/solvation">Solvation</a> (17) </li> <li class="cat-item cat-item-77"> <a href="/blog/archives/category/stereochemistry">Stereochemistry</a> (2) </li> <li class="cat-item cat-item-68"> <a href="/blog/archives/category/stereoinduction">stereoinduction</a> (4) </li> <li class="cat-item cat-item-71"> <a href="/blog/archives/category/tunneling">Tunneling</a> (26) </li> <li class="cat-item cat-item-1"> <a href="/blog/archives/category/uncategorized">Uncategorized</a> (57) </li> <li class="cat-item cat-item-82"> <a href="/blog/archives/category/vibrational-frequencies">vibrational frequencies</a> (3) </li> </ul> </li> <li class="box"> <h2> Monthly </h2> <ul> <li><a href="/blog/archives/date/2019/06">June 2019</a></li> <li><a href="/blog/archives/date/2019/04">April 2019</a></li> <li><a href="/blog/archives/date/2019/03">March 2019</a></li> <li><a href="/blog/archives/date/2019/02">February 2019</a></li> <li><a href="/blog/archives/date/2019/01">January 2019</a></li> <li><a href="/blog/archives/date/2018/12">December 2018</a></li> <li><a href="/blog/archives/date/2018/11">November 2018</a></li> <li><a href="/blog/archives/date/2018/10">October 2018</a></li> <li><a href="/blog/archives/date/2018/09">September 2018</a></li> <li><a href="/blog/archives/date/2018/08">August 2018</a></li> <li><a href="/blog/archives/date/2018/07">July 2018</a></li> <li><a href="/blog/archives/date/2018/06">June 2018</a></li> <li><a href="/blog/archives/date/2018/05">May 2018</a></li> <li><a href="/blog/archives/date/2018/04">April 2018</a></li> <li><a href="/blog/archives/date/2018/03">March 2018</a></li> <li><a href="/blog/archives/date/2018/02">February 2018</a></li> <li><a href="/blog/archives/date/2018/01">January 2018</a></li> <li><a href="/blog/archives/date/2017/12">December 2017</a></li> <li><a href="/blog/archives/date/2017/11">November 2017</a></li> <li><a href="/blog/archives/date/2017/10">October 2017</a></li> <li><a href="/blog/archives/date/2017/09">September 2017</a></li> <li><a href="/blog/archives/date/2017/08">August 2017</a></li> <li><a href="/blog/archives/date/2017/07">July 2017</a></li> <li><a href="/blog/archives/date/2017/06">June 2017</a></li> <li><a href="/blog/archives/date/2017/05">May 2017</a></li> <li><a href="/blog/archives/date/2017/04">April 2017</a></li> <li><a href="/blog/archives/date/2017/03">March 2017</a></li> <li><a href="/blog/archives/date/2017/02">February 2017</a></li> <li><a href="/blog/archives/date/2017/01">January 2017</a></li> <li><a href="/blog/archives/date/2016/12">December 2016</a></li> <li><a href="/blog/archives/date/2016/11">November 2016</a></li> <li><a href="/blog/archives/date/2016/10">October 2016</a></li> <li><a href="/blog/archives/date/2016/09">September 2016</a></li> <li><a href="/blog/archives/date/2016/08">August 2016</a></li> <li><a href="/blog/archives/date/2016/07">July 2016</a></li> <li><a href="/blog/archives/date/2016/06">June 2016</a></li> <li><a href="/blog/archives/date/2016/05">May 2016</a></li> <li><a href="/blog/archives/date/2016/04">April 2016</a></li> <li><a href="/blog/archives/date/2016/03">March 2016</a></li> <li><a href="/blog/archives/date/2016/02">February 2016</a></li> <li><a href="/blog/archives/date/2016/01">January 2016</a></li> <li><a href="/blog/archives/date/2015/12">December 2015</a></li> <li><a href="/blog/archives/date/2015/11">November 2015</a></li> <li><a href="/blog/archives/date/2015/10">October 2015</a></li> <li><a href="/blog/archives/date/2015/09">September 2015</a></li> <li><a href="/blog/archives/date/2015/08">August 2015</a></li> <li><a href="/blog/archives/date/2015/07">July 2015</a></li> <li><a href="/blog/archives/date/2015/06">June 2015</a></li> <li><a href="/blog/archives/date/2015/05">May 2015</a></li> <li><a href="/blog/archives/date/2015/04">April 2015</a></li> <li><a href="/blog/archives/date/2015/03">March 2015</a></li> <li><a href="/blog/archives/date/2015/02">February 2015</a></li> <li><a href="/blog/archives/date/2015/01">January 2015</a></li> <li><a href="/blog/archives/date/2014/12">December 2014</a></li> <li><a href="/blog/archives/date/2014/11">November 2014</a></li> <li><a href="/blog/archives/date/2014/10">October 2014</a></li> <li><a href="/blog/archives/date/2014/09">September 2014</a></li> <li><a href="/blog/archives/date/2014/08" aria-current="page">August 2014</a></li> <li><a href="/blog/archives/date/2014/07">July 2014</a></li> <li><a href="/blog/archives/date/2014/06">June 2014</a></li> <li><a href="/blog/archives/date/2014/05">May 2014</a></li> <li><a href="/blog/archives/date/2014/04">April 2014</a></li> <li><a href="/blog/archives/date/2014/03">March 2014</a></li> <li><a href="/blog/archives/date/2014/02">February 2014</a></li> <li><a href="/blog/archives/date/2014/01">January 2014</a></li> <li><a href="/blog/archives/date/2013/12">December 2013</a></li> <li><a href="/blog/archives/date/2013/11">November 2013</a></li> <li><a href="/blog/archives/date/2013/10">October 2013</a></li> <li><a href="/blog/archives/date/2013/09">September 2013</a></li> <li><a href="/blog/archives/date/2013/08">August 2013</a></li> <li><a href="/blog/archives/date/2013/07">July 2013</a></li> <li><a href="/blog/archives/date/2013/06">June 2013</a></li> <li><a href="/blog/archives/date/2013/05">May 2013</a></li> <li><a href="/blog/archives/date/2013/04">April 2013</a></li> <li><a href="/blog/archives/date/2013/03">March 2013</a></li> <li><a href="/blog/archives/date/2013/02">February 2013</a></li> <li><a href="/blog/archives/date/2013/01">January 2013</a></li> <li><a href="/blog/archives/date/2012/12">December 2012</a></li> <li><a href="/blog/archives/date/2012/11">November 2012</a></li> <li><a href="/blog/archives/date/2012/10">October 2012</a></li> <li><a href="/blog/archives/date/2012/09">September 2012</a></li> <li><a href="/blog/archives/date/2012/08">August 2012</a></li> <li><a href="/blog/archives/date/2012/07">July 2012</a></li> <li><a href="/blog/archives/date/2012/06">June 2012</a></li> <li><a href="/blog/archives/date/2012/05">May 2012</a></li> <li><a href="/blog/archives/date/2012/04">April 2012</a></li> <li><a href="/blog/archives/date/2012/03">March 2012</a></li> <li><a href="/blog/archives/date/2012/02">February 2012</a></li> <li><a href="/blog/archives/date/2012/01">January 2012</a></li> <li><a href="/blog/archives/date/2011/12">December 2011</a></li> <li><a href="/blog/archives/date/2011/11">November 2011</a></li> <li><a href="/blog/archives/date/2011/10">October 2011</a></li> <li><a href="/blog/archives/date/2011/09">September 2011</a></li> <li><a href="/blog/archives/date/2011/08">August 2011</a></li> <li><a href="/blog/archives/date/2011/07">July 2011</a></li> <li><a href="/blog/archives/date/2011/06">June 2011</a></li> <li><a href="/blog/archives/date/2011/05">May 2011</a></li> <li><a href="/blog/archives/date/2011/04">April 2011</a></li> <li><a href="/blog/archives/date/2011/03">March 2011</a></li> <li><a href="/blog/archives/date/2011/02">February 2011</a></li> <li><a href="/blog/archives/date/2011/01">January 2011</a></li> <li><a href="/blog/archives/date/2010/12">December 2010</a></li> <li><a href="/blog/archives/date/2010/11">November 2010</a></li> <li><a href="/blog/archives/date/2010/10">October 2010</a></li> <li><a href="/blog/archives/date/2010/09">September 2010</a></li> <li><a href="/blog/archives/date/2010/08">August 2010</a></li> <li><a href="/blog/archives/date/2010/07">July 2010</a></li> <li><a href="/blog/archives/date/2010/06">June 2010</a></li> <li><a href="/blog/archives/date/2010/05">May 2010</a></li> <li><a href="/blog/archives/date/2010/04">April 2010</a></li> <li><a href="/blog/archives/date/2010/03">March 2010</a></li> <li><a href="/blog/archives/date/2010/02">February 2010</a></li> <li><a href="/blog/archives/date/2010/01">January 2010</a></li> <li><a href="/blog/archives/date/2009/12">December 2009</a></li> <li><a href="/blog/archives/date/2009/11">November 2009</a></li> <li><a href="/blog/archives/date/2009/10">October 2009</a></li> <li><a href="/blog/archives/date/2009/09">September 2009</a></li> <li><a href="/blog/archives/date/2009/08">August 2009</a></li> <li><a href="/blog/archives/date/2009/07">July 2009</a></li> <li><a href="/blog/archives/date/2009/06">June 2009</a></li> <li><a href="/blog/archives/date/2009/05">May 2009</a></li> <li><a href="/blog/archives/date/2009/04">April 2009</a></li> <li><a href="/blog/archives/date/2009/03">March 2009</a></li> <li><a href="/blog/archives/date/2009/02">February 2009</a></li> <li><a href="/blog/archives/date/2009/01">January 2009</a></li> <li><a href="/blog/archives/date/2008/12">December 2008</a></li> <li><a href="/blog/archives/date/2008/11">November 2008</a></li> <li><a href="/blog/archives/date/2008/10">October 2008</a></li> <li><a href="/blog/archives/date/2008/09">September 2008</a></li> <li><a href="/blog/archives/date/2008/08">August 2008</a></li> <li><a href="/blog/archives/date/2008/07">July 2008</a></li> <li><a href="/blog/archives/date/2008/06">June 2008</a></li> <li><a href="/blog/archives/date/2008/05">May 2008</a></li> <li><a href="/blog/archives/date/2008/04">April 2008</a></li> <li><a href="/blog/archives/date/2008/03">March 2008</a></li> <li><a href="/blog/archives/date/2008/02">February 2008</a></li> <li><a href="/blog/archives/date/2008/01">January 2008</a></li> <li><a href="/blog/archives/date/2007/12">December 2007</a></li> <li><a href="/blog/archives/date/2007/11">November 2007</a></li> <li><a href="/blog/archives/date/2007/10">October 2007</a></li> <li><a href="/blog/archives/date/2007/09">September 2007</a></li> <li><a href="/blog/archives/date/2007/08">August 2007</a></li> <li><a href="/blog/archives/date/2007/07">July 2007</a></li> </ul> </li> </ul> <a rel="license" href="https://creativecommons.org/licenses/by-nd/3.0/"> <img alt="Creative Commons License" style="border-width:0" 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