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<html> <head> <title>Computational Organic Chemistry by Steven M. Bachrach</title> <meta name="author" content="Steven Bachrach" /> <meta name="copyright" content="© 2007 Steven Bachrach" /> <meta name="description" content="The supplemental website to Steven Bachrach's book Computational Organic Chemistry" /> <meta name="keywords" content="chemistry, organic, organic chemistry, computational chemistry, computational, book, wiley, steven bachrach, bachrach, steven m. bachrach, steven m bachrach" /> <meta http-equiv="content-type" content="text/html; charset=UTF-16" /> <link rel="stylesheet" href="style.css" type="text/css" media="screen" /> <link rel="shortcut icon" href="favicon.ico" type="image/x-icon" /> </head> <body> <div id="header"> <div id="header_img"></div> </div> <div id="sidebar_background"></div> <div id="wrapper1"> <div id="wrapper2"> <div id="maincol"> <div id="leftcol"> <a href="http://www.wiley.com/WileyCDA/WileyTitle/productCd-1118291921,subjectCd-CHD0.html"> <img src="COC2_cover.jpg" alt="Book Cover" /> <li>Buy the book now</li> </a> </div> <div id="rightcol"> <h3>About the Book</h3> <ul> <li>» <a href="index.html">Home</a></li> <li>» <a href="/blog/">Read the blog</a></li> <li>» <a href="http://www.trinity.edu/sbachrac/">Steven M. Bachrach</a></li> <li>» <a href="http://www.trinity.edu/">Trinity University</a></li> <li>» <a href="http://www.wiley.com/">Published by Wiley</a></li> <li>» <a href="indexFirst.html">First Edition Web Page</a></li> </ul> <h3>Citations</h3> <ul> <li>» <a href="CitationsSPref.htm">Preface</a></li> <li>» <a href="CitationsS1.htm">Chapter 1</a></li> <li>» <a href="CitationsS2.htm">Chapter 2</a></li> <li>» <a href="CitationsS3.htm">Chapter 3</a></li> <li>» <a href="CitationsS4.htm">Chapter 4</a></li> <li>» <a href="CitationsS5.htm">Chapter 5</a></li> <li>» <a href="CitationsS6.htm">Chapter 6</a></li> <li>» <a href="CitationsS7.htm">Chapter 7</a></li> <li>» <a href="CitationsS8.htm">Chapter 8</a></li> <li>» <a href="CitationsS9.htm">Chapter 9</a></li> </ul> <h3>Molecules</h3> <ul> <li>» Under Construction</li> </ul> </div> <div id="centercol"> <h1>Chapter 3 Citations</h1> <ol> <li>Feng, Y.; Liu, L.; Wang, J.-T.; Huang, H.; Guo, Q.-X. "Assessment of Experimental Bond Dissociation Energies Using Composite ab Initio Methods and Evaluation of the Performances of Density Functional Methods in the Calculation of Bond Dissociation Energies," J. Chem. Inf. Comput. Sci. 2003, 43, 2005-2013, DOI: <a href="http://dx.doi.org/10.1021/ci034033k">10.1021/ci034033k</a>.</li> <li> Blanksby, S. J.; Ellison, G. B. "Bond Dissociation Energies of Organic Molecules," Acc. Chem. Res. 2003, 36, 255-263, DOI: <a href="http://dx.doi.org/10.1021/ar020230d">10.1021/ar020230d</a>.</li> <li> Henry, D. J.; Parkinson, C. J.; Mayer, P. M.; Radom, L. "Bond Dissociation Energies and Radical Stabilization Energies Associated with Substituted Methyl Radicals," J. Phys. Chem. A 2001, 105, 6750-6756, DOI: <a href="http://dx.doi.org/10.1021/jp010442c">10.1021/jp010442c</a>.</li> <li> Feng, Y.; Liu, L.; Wang, J.-T.; Zhao, S.-W.; Guo, Q.-X. "Homolytic C-H and N-H Bond Dissociation Energies of Strained Organic Compounds," J. Org. Chem. 2004, 69, 3129-3138, DOI: <a href="http://dx.doi.org/10.1021/jo035306d">10.1021/jo035306d</a>.</li> <li> Menon, A. S.; Wood, G. P. F.; Moran, D.; Radom, L. "Bond Dissociation Energies and Radical Stabilization Energies: An Assessment of Contemporary Theoretical Procedures," J. Phys. Chem. A 2007, 111, 13638-13644, DOI: <a href="http://dx.doi.org/10.1021/jp076521r">10.1021/jp076521r</a>.</li> <li> Yao, X.-Q.; Hou, X.-J.; Jiao, H.; Xiang, H.-W.; Li, Y.-W. "Accurate Calculations of Bond Dissociation Enthalpies with Density Functional Methods," J. Phys. Chem. A 2003, 107, 9991-9996, DOI: <a href="http://dx.doi.org/10.1021/jp0361125">10.1021/jp0361125</a>.</li> <li> Check, C. E.; Gilbert, T. M. "Progressive Systematic Underestimation of Reaction Energies by the B3LYP Model as the Number of C-C Bonds Increases: Why Organic Chemists Should Use Multiple DFT Models for Calculations Involving Polycarbon Hydrocarbons," J. Org. Chem. 2005, 70, 9828-9834, DOI: <a href="http://dx.doi.org/10.1021/jo051545k">10.1021/jo051545k</a>.</li> <li> Redfern, P. C.; Zapol, P.; Curtiss, L. A.; Raghavachari, K. "Assessment of Gaussian-3 and Density Functional Theories for Enthalpies of Formation of C1-C16 Alkanes," J. Phys. Chem. A 2000, 104, 5850-5854, DOI: <a href="http://dx.doi.org/10.1021/jp994429s">10.1021/jp994429s</a>.</li> <li> Luo, Y.-R. Handbook of Bond Dissociation Energies in Organic Compounds; CRC Press: New York, 2002.</a></li> <li> Rüchardt, C. "Relations Between Structure and Reactivity in Free-Radical Chemistry," Angew. Chem. Int. Ed. Engl. 1970, 9, 830-843, DOI: <a href="http://dx.doi.org/10.1002/anie.197008301">10.1002/anie.197008301</a>.</li> <li> Izgorodina, E. I.; Coote, M. L.; Radom, L. "Trends in R-X Bond Dissociation Energies (R = Me, Et, i-Pr, t-Bu; X = H, CH3, OCH3, OH, F): A Surprising Shortcoming of Density Functional Theory," J. Phys. Chem. 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"NIST Chemistry WebBook, NIST Standard Reference Database Number 69," 2012, URL: <a href="http://webbook.nist.gov/"> http://webbook.nist.gov/.</a></li> <li> Kollmar, H. "The Stability of Alkyl Anions. A Molecular Orbital Theoretical Study," J. Am. Chem. Soc. 1978, 100, 2665-2669, DOI: <a href="http://dx.doi.org/10.1021/ja00477a016">10.1021/ja00477a016</a>.</li> <li> Chandrasekhar, J.; Andrade, J. G.; Schleyer, P. v. R. "Efficient and Accurate Calculation of Anion Proton Affinities," J. Am. Chem. Soc. 1981, 103, 5609-5612, DOI: <a href="http://dx.doi.org/10.1021/ja00408a074">10.1021/ja00408a074</a>.</li> <li> Saunders, W. H., Jr. "Ab Initio and Semi-Empirical Investigation of Gas-Phase Carbon Acidity," J. Phys. Org. Chem. 1994, 7, 268-271, DOI: <a href="http://dx.doi.org/10.1002/poc.610070509">10.1002/poc.610070509</a>.</li> <li> Burk, P.; Koppel, I. A.; Koppel, I.; Leito, I.; Travnikova, O. 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"Cubyl Anion Formation and an Experimental Determination of the Acidity and C-H Bond Dissociation Energy of Cubane," J. Am. Chem. Soc. 1997, 119, 237-238, DOI: <a href="http://dx.doi.org/10.1021/ja9627858">10.1021/ja9627858</a>.</li> <li> Rayne, S.; Forest, K. "Gas-phase enthalpies of formation, acidities, and strain energies of the [m,n]polyprismanes (m ≥ 2; n = 3-8; m x n  ≤ 16): a CBS-Q//B3, G4MP2, and G4 theoretical study," Theor. Chem. Acc. 2010, 127, 697-709, DOI: <a href="http://dx.doi.org/10.1007/s00214-010-0780-0">10.1007/s00214-010-0780-0</a>.</li> <li> Broadus, K. M.; Kass, S. R.; Osswald, T.; Prinzbach, H. "Dodecahedryl Anion Formation and an Experimental Determination of the Acidity and C-H Bond Dissociation Energy of Dodecahedrane," J. Am. Chem. Soc. 2000, 122, 10964-10968, DOI: <a href="http://dx.doi.org/10.1021/ja002588f">10.1021/ja002588f</a>.</li> <li> Fattahi, A.; McCarthy, R. E.; Ahmad, M. R.; Kass, S. R. "Why Does Cyclopropene Have the Acidity of an Acetylene but the Bond Energy of Methane?," J. Am. Chem. Soc. 2003, 125, 11746-11750, DOI: <a href="http://dx.doi.org/10.1021/ja035725s">10.1021/ja035725s</a>.</li> <li> Manini, P.; Amrein, W.; Gramlich, V.; Diederich, F. "Expanded Cubane: Synthesis of a Cage Compound with a C56 Core by Acetylenic Scaffolding and Gas-Phase Transformations into Fullerenes," Angew. Chem. Int. Ed. 2002, 4339-4343, DOI: <a href="http://dx.doi.org/10.1002/1521-3773(20021115)41:22%3c4339::AID-ANIE4339%3e3.0.CO;2-8">10.1002/1521-3773(20021115)41:22<4339::AID-ANIE4339>3.0.CO;2-8</a>.</li> <li> Bachrach, S. M. "Structure, Deprotonation Energy, and Cation Affinity of an Ethynyl-Expanded Cubane," J. Phys. Chem. A. 2003, 107, 4957-4961, DOI: <a href="http://dx.doi.org/10.1021/jp034406k">10.1021/jp034406k</a>.</li> <li> Bachrach, S. M.; Demoin, D. W. "Computational Studies of Ethynyl- and Diethynyl-Expanded Tetrahedranes, Prismanes, Cubanes, and Adamantanes," J. Org. 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