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\u3010March\u9ad8\u7b49\u6709\u6a5f\u5316\u5b78\u2014\u53cd\u61c9\u3001\u6a5f\u7406\u8207\u7d50\u69cb\u3011\uff08\u539f\u8457\u7b2c7\u7248\uff09
<\/span><\/strong><\/p>\n

\u7de8\u8f2f\u63a8\u85a6<\/span><\/strong><\/p>\n

\u9069\u8b80\u4eba\u7fa4 \uff1a\u672c\u66f8\u9069\u5408\u4f5c\u70ba\u9ad8\u5e74\u7d1a\u548c\u7814\u7a76\u751f\u6709\u6a5f\u5316\u5b78\u6559\u6750\uff0c\u4f4e\u5e74\u7d1a\u57fa\u790e\u6709\u6a5f\u5316\u5b78\u8ab2\u7a0b\u7684\u6559\u5e2b\u7528\u66f8\uff0c\u4ee5\u53ca\u6709\u6a5f\u5316\u5b78\u5de5\u5177\u66f8\u3002<\/p>\n

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\u50cf\u8fad\u5178\u4e00\u6a23\u7684\u66f8\uff0c\u5206\u985e\u975e\u5e38\u8a73\u7d30\uff0c\u4e09\u7d1a\u7d22\u5f15\u3001\u4eba\u540d\u7d22\u5f15\u3001\u53cd\u61c9\u985e\u578b\u7d22\u5f15\u7b49\u53ef\u4ee5\u6307\u5f15\u8b80\u8005\u5feb\u901f\u627e\u5230\u60f3\u8981\u627e\u7684\u5167\u5bb9\u3002<\/p>\n

\u6a5f\u7406\u5256\u6790\u5f97\u6df1\u5165\u8a73\u76e1\uff0c\u53c3\u8003\u6587\u737b\u975e\u5e38\u591a\uff0c\u5dee\u4e0d\u591a\u6bcf\u53e5\u8a71\u90fd\u6709\uff0c\u975e\u5e38\u9069\u5408\u6709\u6a5f\u5316\u5b78\u9ad8\u5e74\u7d1a\u540c\u5b78\u6216\u66f4\u9ad8\u7d1a\u7684\u79d1\u7814\u5de5\u4f5c\u8005\u3002<\/p>\n

\u503c\u5f97\u6bcf\u4e00\u4f4d\u6709\u6a5f\u5316\u5b78\u4eba\u64c1\u6709\u300aMarch\u9ad8\u7b49\u6709\u6a5f\u5316\u5b78\u300b\u7d93\u5178\u8457\u4f5c\u3002<\/p>\n

\u5716\u66f8\u6846\u67b6\u6cbf\u8972\u4e86\u4e4b\u524d\u7684\u6574\u9ad4\u69cb\u67b6\uff0c\u5206\u5169\u7bc7\uff0c\u4e0a\u7bc7\u539f\u7406\u7bc7\uff0c\u4e0b\u7bc7\u53cd\u61c9\u7bc7\u3002\u5167\u5bb9\u6574\u9ad4\u8b8a\u52d5\u4e0d\u5927\uff0c\u500b\u5225\u6846\u67b6\u7d50\u69cb\u6709\u4e9b\u8abf\u6574\uff0c\u5716\u66f8\u8b8a\u52d5\u8f03\u5927\u7684\u662f\u5c0d\u6587\u737b\u7684\u66f4\u65b0\uff0c\u589e\u52a0\u4e865500\u9918\u689d2005-2013\u5e74\u7684\u53c3\u8003\u6587\u737b\uff0c\u522a\u9664\u4e86\u4e00\u4e9b\u8001\u7684\u6587\u737b\u548c\u90e8\u5206\u53cd\u61c9\u3002<\/p>\n

\u5167\u5bb9\u7c21\u4ecb<\/span><\/strong><\/p>\n

\u672c\u66f8\u662fMichael B Smith\u6559\u6388\u7de8\u8457\u7684\u300aMarch\u2019s Advanced Organic Chemistry\u300b\u7b2c\u4e03\u7248\u7684\u4e2d\u6587\u8b6f\u672c\uff0c\u662f\u9ad8\u7b49\u6709\u6a5f\u5316\u5b78\u7684\u7d93\u5178\u6559\u6750\u3002\u8a72\u66f8\u5167\u5bb9\u5168\u9762\uff0c\u689d\u7406\u6e05\u6670\uff0c\u901a\u904e\u6709\u6a5f\u5316\u5b78\u65e5\u76ca\u767c\u5c55\u7684\u65b0\u65b9\u6cd5\u3001\u65b0\u6280\u8853\u7cfb\u7d71\u5730\u8b1b\u8ff0\u6709\u6a5f\u5316\u5b78\u7684\u57fa\u672c\u7406\u8ad6\u3001\u4e26\u8b1b\u8ff0\u5982\u4f55\u904b\u7528\u65b0\u7406\u8ad6\u3001\u65b0\u65b9\u6cd5\u4f86\u89e3\u91cb\u6709\u6a5f\u5316\u5b78\u53cd\u61c9\u4e2d\u7684\u65b0\u73fe\u8c61\u3002\u66f8\u4e2d\u6839\u64da\u53cd\u61c9\u985e\u578b\u7d66\u51fa\u4e86\u5927\u91cf\u7684\u53cd\u61c9\u4e26\u6536\u96c6\u4e86\u5927\u91cf\u7684\u6587\u737b\u3002\u672c\u66f8\u9069\u5408\u4f5c\u70ba\u9ad8\u5e74\u7d1a\u548c\u7814\u7a76\u751f\u6709\u6a5f\u5316\u5b78\u6559\u6750\uff0c\u4f4e\u5e74\u7d1a\u57fa\u790e\u6709\u6a5f\u5316\u5b78\u8ab2\u7a0b\u7684\u6559\u5e2b\u7528\u66f8\uff0c\u4ee5\u53ca\u6709\u6a5f\u5316\u5b78\u5de5\u5177\u66f8\u3002<\/p>\n

\u76ee\u9304<\/span><\/strong><\/p>\n

\u4e0a\u7bc7<\/p>\n

\u7b2c1\u7ae0\u5b9a\u57df\u5316\u5b78\u93752<\/p>\n

1.1\u5171\u50f9\u93752<\/p>\n

1.2\u591a\u50f9\u614b3<\/p>\n

1.3\u96dc\u53164<\/p>\n

1.4\u591a\u91cd\u93755<\/p>\n

1.5\u5149\u96fb\u5b50\u80fd\u8b5c6<\/p>\n

1.6\u5206\u5b50\u7684\u96fb\u5b50\u7d50\u69cb7<\/p>\n

1.7\u96fb\u8ca0\u60278<\/p>\n

1.8\u5076\u6975\u77e99<\/p>\n

1.9\u8a98\u5c0e\u6548\u61c9\u548c\u5834\u6548\u61c99<\/p>\n

1.10\u9375\u957710<\/p>\n

1.11\u9375\u89d212<\/p>\n

1.12\u9375\u80fd13<\/p>\n

\u53c3\u8003\u6587\u737b14<\/p>\n

\u7b2c2\u7ae0\u96e2\u57df\u5316\u5b78\u937518<\/p>\n

2.1\u5206\u5b50\u8ecc\u905318<\/p>\n

2.2\u542b\u96e2\u57df\u9375\u5316\u5408\u7269\u7684\u9375\u80fd\u548c\u9375\u957720<\/p>\n

2.3\u542b\u6709\u96e2\u57df\u9375\u5206\u5b50\u7684\u7a2e\u985e20<\/p>\n

2.4\u4ea4\u53c9\u5171\u8edb23<\/p>\n

2.5\u5171\u632f\u898f\u524723<\/p>\n

2.6\u5171\u632f\u6548\u61c924<\/p>\n

2.7\u5171\u632f\u7684\u4f4d\u963b\u6548\u61c9\u548c\u5f35\u529b\u5f71\u97ff24<\/p>\n

2.8p\u03c0-d\u03c0\u9375\uff1a\u5167\u9e7d26<\/p>\n

2.9\u82b3\u9999\u602726<\/p>\n

2.9.1\u516d\u5143\u74b028<\/p>\n

2.9.2\u4e94\u5143\u3001\u4e03\u5143\u548c\u516b\u5143\u74b029<\/p>\n

2.9.3\u5176\u5b83\u542b\u6709\u82b3\u9999\u516d\u9685\u9ad4\u7684\u9ad4\u7cfb31<\/p>\n

2.10\u4ea4\u66ff\u7684\u548c\u975e\u4ea4\u66ff\u7684\u70f432<\/p>\n

2.11\u96fb\u5b50\u6578\u4e0d\u662f6\u7684\u82b3\u9999\u9ad4\u7cfb33<\/p>\n

2.11.1\u96d9\u96fb\u5b50\u9ad4\u7cfb33<\/p>\n

2.11.2\u56db\u96fb\u5b50\u9ad4\u7cfb\uff1a\u53cd\u82b3\u9999\u602734<\/p>\n

2.11.3\u516b\u96fb\u5b50\u9ad4\u7cfb35<\/p>\n

2.11.4\u5341\u96fb\u5b50\u9ad4\u7cfb35<\/p>\n

2.11.5\u8d85\u904e10\u500b\u96fb\u5b50\u7684\u9ad4\u7cfb\uff1a4n+2\u96fb\u5b5036<\/p>\n

2.11.6\u8d85\u904e10\u500b\u96fb\u5b50\u7684\u9ad4\u7cfb\uff1a4n\u96fb\u5b5038<\/p>\n

2.12\u5176\u5b83\u82b3\u9999\u5316\u5408\u726940<\/p>\n

2.13\u8d85\u5171\u8edb41<\/p>\n

2.14\u4e92\u8b8a\u7570\u69cb42<\/p>\n

2.14.1\u916e-\u70ef\u9187\u4e92\u8b8a\u7570\u69cb43<\/p>\n

2.14.2\u5176\u5b83\u8cea\u5b50\u9077\u79fb\u4e92\u8b8a\u7570\u69cb44<\/p>\n

\u53c3\u8003\u6587\u737b45<\/p>\n

\u7b2c3\u7ae0\u6bd4\u5171\u50f9\u9375\u5f31\u7684\u4f5c\u752858<\/p>\n

3.1\u6c2b\u937558<\/p>\n

3.2\u03c0-\u03c0\u76f8\u4e92\u4f5c\u752860<\/p>\n

3.3\u52a0\u5408\u5316\u5408\u726961<\/p>\n

3.3.1\u96fb\u5b50\u4f9b\u9ad4-\u53d7\u9ad4(EDA)\u8907\u5408\u726961<\/p>\n

3.3.2\u51a0\u919a\u8907\u5408\u7269\u548c\u7a74\u72c0\u5316\u5408\u726962<\/p>\n

3.3.3\u5305\u542b\u5316\u5408\u726964<\/p>\n

3.3.4\u74b0\u7cca\u7cbe65<\/p>\n

3.4\u7d22\u70f4\u548c\u8f2a\u70f766<\/p>\n

3.5\u846b\u8606\uff3bn\uff3d\u8132\u57fa\u9640\u87ba\u70f767<\/p>\n

\u53c3\u8003\u6587\u737b67<\/p>\n

\u7b2c4\u7ae0\u7acb\u9ad4\u5316\u5b7874<\/p>\n

4.1\u5149\u5b78\u6d3b\u6027\u8207\u624b\u602774<\/p>\n

4.1.1\u65cb\u5149\u5ea6\u8207\u6e2c\u91cf\u689d\u4ef6\u7684\u95dc\u4fc275<\/p>\n

4.2\u4ec0\u9ebc\u6a23\u7684\u5206\u5b50\u5177\u6709\u5149\u5b78\u6d3b\u602775<\/p>\n

4.3Fischer\u6295\u5f71\u5f0f79<\/p>\n

4.4\u7d55\u5c0d\u69cb\u578b80<\/p>\n

4.4.1Cahn-Ingold-Prelog\u9ad4\u7cfb80<\/p>\n

4.4.2\u6e2c\u5b9a\u69cb\u578b\u7684\u65b9\u6cd582<\/p>\n

4.5\u5149\u5b78\u6d3b\u6027\u7684\u7522\u751f83<\/p>\n

4.6\u542b\u6709\u4e0d\u6b62\u4e00\u500b\u624b\u6027\u4e2d\u5fc3\u7684\u5206\u5b5084<\/p>\n

4.7\u4e0d\u5c0d\u7a31\u5408\u621085<\/p>\n

4.8\u62c6\u5206\u7684\u65b9\u6cd587<\/p>\n

4.9\u5149\u5b78\u7d14\u5ea689<\/p>\n

4.10\u9806\u53cd\u7570\u69cb90<\/p>\n

4.10.1\u7531\u96d9\u9375\u5f15\u8d77\u7684\u9806\u53cd\u7570\u69cb90<\/p>\n

4.10.2\u55ae\u74b0\u5316\u5408\u7269\u7684\u9806\u53cd\u7570\u69cb91<\/p>\n

4.10.3\u7a20\u74b0\u548c\u6a4b\u74b0\u7cfb\u7684\u9806\u53cd\u7570\u69cb92<\/p>\n

4.11\u5916-\u5167\u7570\u69cb93<\/p>\n

4.12\u5c0d\u6620\u7570\u4f4d\u548c\u975e\u5c0d\u6620\u7570\u4f4d\u7684\u539f\u5b50\u3001\u57fa\u5718\u548c\u9eb593<\/p>\n

4.13\u7acb\u9ad4\u5c08\u4e00\u6027\u548c\u7acb\u9ad4\u9078\u64c7\u6027\u5408\u621095<\/p>\n

4.14\u69cb\u8c61\u5206\u679095<\/p>\n

4.14.1\u958b\u93c8\u9ad4\u7cfb\u69cb\u8c6196<\/p>\n

4.14.2\u516d\u5143\u74b0\u69cb\u8c6198<\/p>\n

4.14.3\u542b\u96dc\u539f\u5b50\u7684\u516d\u5143\u74b0\u69cb\u8c61100<\/p>\n

4.14.4\u5176\u5b83\u74b0\u69cb\u8c61101<\/p>\n

4.15\u5206\u5b50\u529b\u5b78101<\/p>\n

4.16\u5f35\u529b102<\/p>\n

4.16.1\u5c0f\u74b0\u4e2d\u7684\u5f35\u529b103<\/p>\n

4.16.2\u5176\u5b83\u74b0\u4e2d\u7684\u5f35\u529b105<\/p>\n

4.16.3\u4e0d\u98fd\u548c\u74b0106<\/p>\n

4.16.4\u7121\u6cd5\u907f\u514d\u64c1\u64e0\u6240\u5c0e\u81f4\u7684\u5f35\u529b107<\/p>\n

\u53c3\u8003\u6587\u737b109<\/p>\n

\u7b2c5\u7ae0\u78b3\u6b63\u96e2\u5b50\u3001\u78b3\u8ca0\u96e2\u5b50\u3001\u81ea\u7531\u57fa\u3001\u5361\u8cd3\u548c\u6c2e\u70ef124<\/p>\n

5.1\u78b3\u6b63\u96e2\u5b50124<\/p>\n

5.1.1\u547d\u540d124<\/p>\n

5.1.2\u78b3\u6b63\u96e2\u5b50\u7684\u7a69\u5b9a\u6027\u548c\u7d50\u69cb124<\/p>\n

5.1.3\u78b3\u6b63\u96e2\u5b50\u7684\u7522\u751f\u548c\u6e6e\u6ec5128<\/p>\n

5.2\u78b3\u8ca0\u96e2\u5b50129<\/p>\n

5.2.1\u7a69\u5b9a\u6027\u548c\u7d50\u69cb129<\/p>\n

5.2.2\u91d1\u5c6c\u6709\u6a5f\u5316\u5408\u7269\u7684\u7d50\u69cb132<\/p>\n

5.2.3\u78b3\u8ca0\u96e2\u5b50\u7684\u7522\u751f\u548c\u6e6e\u6ec5134<\/p>\n

5.3\u81ea\u7531\u57fa134<\/p>\n

5.3.1\u7a69\u5b9a\u6027\u548c\u7d50\u69cb134<\/p>\n

5.3.2\u81ea\u7531\u57fa\u7684\u7522\u751f\u548c\u6e6e\u6ec5138<\/p>\n

5.3.3\u81ea\u7531\u57fa\u96e2\u5b50140<\/p>\n

5.4\u5361\u8cd3140<\/p>\n

5.4.1\u7a69\u5b9a\u6027\u548c\u7d50\u69cb140<\/p>\n

5.4.2\u5361\u8cd3\u7684\u7522\u751f\u548c\u6e6e\u6ec5141<\/p>\n

5.5\u6c2e\u70ef143<\/p>\n

\u66f8\u6458\u63d2\u756b<\/span><\/strong><\/p>\n

<\/p>\n

———————————————————————–
\"1.jpg\"\/<\/p>\n

\u3010\u9ad8\u7b49\u6709\u6a5f\u5316\u5b78\uff1a\u7d50\u69cb\u8207\u6a5f\u7406\uff08\u82f1\u7248\uff09\u3011<\/span><\/strong><\/p>\n

\u5167\u5bb9\u7c21\u4ecb<\/span><\/strong><\/p>\n

\u81ea\u5f9e1977\u5e74\u554f\u4e16\u4ee5\u4f86\uff0c\u300a\u9ad8\u7b49\u6709\u6a5f\u5316\u5b78\u300b\u4f5c\u70ba\u5b78\u79d1**\u6559\u6750\u7684\u5730\u4f4d\u4e00\u76f4\u6c92\u6709\u52d5\u6416\u904e\uff0c\u5ee3\u6cdb\u5730\u8986\u84cb\u4e86\u6709\u6a5f\u5316\u5408\u7269\u7684\u7d50\u69cb\u3001\u53cd\u61c9\u6d3b\u6027\u53ca\u5408\u6210\u3002 \u5979\u7684\u7b2c\u4e94\u7248\u76f8\u5c0d2001\u5e74\u51fa\u7248\u7684\u7b2c\u56db\u7248\u9032\u884c\u4e86\u5927\u5e45\u5ea6\u7684\u4fee\u8a02\uff0c\u66f4\u65b0\u4e86\u5b78\u79d1\u767c\u5c55\u7684\u76f8\u95dc\u8cc7\u6599\uff0c\u5167\u5bb9\u7d44\u7e54\u66f4\u52a0\u6e05\u6670\u660e\u6717\uff0c\u7279\u5225\u662f\u8a08\u7b97\u5316\u5b78\u90e8\u5206\u3002 PartA\u5f9e\u5316\u5408\u7269\u7d50\u69cb\u548c\u7acb\u9ad4\u5316\u5b78\u57fa\u790e\u6982\u5ff5\u8b1b\u8d77\uff0c\u6d89\u53ca\u6709\u6a5f\u5316\u5b78\u53cd\u61c9\u71b1\u529b\u5b78\u548c\u52d5\u529b\u5b78\u7684\u65b9\u65b9\u9762\u9762\u3002 \u4e3b\u8981\u53cd\u61c9\u985e\u578b\u6db5\u84cb\u89aa\u6838\u53d6\u4ee3\u53cd\u61c9\u3001\u52a0\u6210\u53cd\u61c9\u3001\u78b3\u8ca0\u96e2\u5b50\u548c\u7fb0\u57fa\u5316\u5b78\u53cd\u61c9\u3001\u82b3\u74b0\u53d6\u4ee3\u53cd\u61c9\u3001\u5468\u74b0\u53cd\u61c9\u3001\u81ea\u7531\u57fa\u53cd\u61c9\u548c\u5149\u5316\u5b78\u53cd\u61c9\u3002 \u6bcf\u7ae0\u5f8c\u9644\u6709\u7fd2\u984c\u7cbe\u9078\u53ca\u89e3\u7b54\u7fd2\u984c\u7684\u63a8\u85a6\u53c3\u8003\u6587\u737b\u3002<\/p>\n

\u76ee\u9304<\/span><\/strong><\/p>\n

Contents<\/p>\n

Preface v<\/p>\n

Acknowledgment and Personal Statement vii<\/p>\n

Introduction ix<\/p>\n

Chapter 1 Chemical Bonding and Molecular Structure 1<\/p>\n

Introduction ix<\/p>\n

1.1 Description of Molecular Structure Using Valence Bond Concepts 2<\/p>\n

1 1.1 Hybridization 4<\/p>\n

1.1.2 The Origin of Electron-Electron Repulsion 7<\/p>\n

1.1.3 Electronegativity and Polarity 8<\/p>\n

1.1.4 Electronegativity Equahzat10n 11<\/p>\n

1.1.5 Differential Electronegativity of Carbon Atoms 12<\/p>\n

1.1.6 Polarizability\uff0cHardness\uff0cand Softness 14<\/p>\n

1.1.7 Resonance and Conjugation 18<\/p>\n

1.1.8 Hyperconjugation 22<\/p>\n

1.1.9 Covalent and van der Waals Radii of Atoms 24<\/p>\n

1.2 Molecular Orbital Theory and Methods 26<\/p>\n

I 2.1 The Huckel MO Method 27<\/p>\n

1.2.2 Semiempirical MO Methods 32<\/p>\n

1.2.3 Ab Initio Methods 32<\/p>\n

1.2.4 Pictorial Representation of MOs for Molecules 35<\/p>\n

1.2.5 Qualitative Application of MO Theory to Reactivity: Perturbational MO Theory and Frontier Orbitals 41<\/p>\n

1.2.6 Numerical Application of MO Theory 50<\/p>\n

1.3 Electron Density Functionals 54<\/p>\n

1.4 Representation of Electron Density Distribution 57<\/p>\n

1.4 1 Mululliken Populat10n Analysis 60<\/p>\n

1.4.2 Natural Bond Orbitals and Natural Population Analysis 61<\/p>\n

1.4.3 Atoms m Molecules 63<\/p>\n

1.4.4 Comparison and Interpretation of Atomic Charge Calculations 70<\/p>\n

1.4.5 Electrostatic Potential Surfaces 73<\/p>\n

1.4.6 Relationships between Electron Density and Bond Order 76<\/p>\n

Topic 1.1 The Origin of the Rotational\uff08Torsional\uff09Barrier in Ethane and Other Small Molecules 78<\/p>\n

Topic 1.2 Heteroatom Hyperconjugation\uff08Anomeric Effect\uff09in Acyclic Molecules 81<\/p>\n

Topic 1.3 Bonding in Cyclopropane and Other Small Ring Compounds 85<\/p>\n

Topic 1.4 Representation of Electron Density by the Laplacian Function 92<\/p>\n

Topic 1.5 Application of Density Functional Theory to Chemical Properties and Reactivity 94<\/p>\n

T.1.5.1 DFT Formulation of Chemical Potential\uff0cElectronegativity\uff0cHardness and Softness\uff0cand Covalent and van der Waal Radii 95<\/p>\n

T.1.5.2 DFT Formulation of Reactivity-The Fukui Function 97<\/p>\n

T.1.5.3 DFT Concepts of Substituent Groups Effects 100<\/p>\n

General References 106<\/p>\n

Problems 106<\/p>\n

Chapter 2 Stereochemistry\uff0cConformation\uff0cand Stereoselectivity 119<\/p>\n

Introduction 119<\/p>\n

2.1 Configuration 119<\/p>\n

2.1.1 Configuration at Double Bonds 119<\/p>\n

2.1.2 Configuration of Cyclic Compounds 121<\/p>\n

2.1.3 Configuration at Tetrahedral Atoms 122<\/p>\n

2.1.4 Molecules with Multiple Stereogenic Centers 126<\/p>\n

2.1.5 Other Types of Stereogenic Centers 128<\/p>\n

2.1.6 The Relationship between Chirality and Symmetry 131<\/p>\n

2.1 7 Configuration at Prochiral Centers 133<\/p>\n

2.1.8 Resolution\u2014The Separation of Enantiomers 136<\/p>\n

2.2 Conformation 142<\/p>\n

2.2 l Conformation of Acyclic Compounds 142<\/p>\n

2.2.2 Conformations of Cyclohexane Derivatives 152<\/p>\n

2.2.3 Conformations of Carbocyclic Rings of Other Sizes 161<\/p>\n

2.3 Molecular Mechanics 167<\/p>\n

2.4 Stereoselective and Stereospecific Reactions 169<\/p>\n

2.4.1 Examples of Stereoselective Reactions 170<\/p>\n

2.4.2 Examples of Stereospecific Reactions 182<\/p>\n

2.5 Enantioselective React10ns 189<\/p>\n

2.5.1 Enantioselective Hydrogenation 189<\/p>\n

2.5.2 Enantioselective Reduction of Ketones 193<\/p>\n

2.5.3 Enantioselective Epoxidation of Allylic Alcohols 196<\/p>\n

2.5.4 Enantioselective Dihydroxylation of Alkenes 200<\/p>\n

2.6 Double Stereodifferentiation: Reinforcing and Competing Stereoselect1v1ty 204<\/p>\n

Topic 2.1 Analysis and Separation of Enantiomeric Mixtures 208<\/p>\n

T.2.1.1 Chiral Shift Reagents and Chiral Solvating Agents 208<\/p>\n

T.2.1.2 Separation of Enantiomers 211<\/p>\n

Topic 2.2 Enzymatic Resolution and Desymmetrization 215<\/p>\n

T.2.2.1 Li pases and Esterases 216<\/p>\n

T.2.2.2 Proteases and Acy lases 222<\/p>\n

T.2.2.3 Epoxide Hydrolases 224<\/p>\n

Topic 2.3 The Anomeric Effect in Cyclic Compounds 227<\/p>\n

Topic 2.4 Polar Substituent Effects in Reduction of Carbonyl Compounds 234<\/p>\n

General References 239<\/p>\n

Problems 240<\/p>\n

Chapter 3 Structural Effects on Stability and Reactivity 253<\/p>\n

Introduction 253<\/p>\n

3.1 Thermodynamic Stability 254<\/p>\n

3.1.1 Relationship between Structure and Thermodynamic Stability for Hydrocarbons 256<\/p>\n

3.1.2 Calculation of Enthalpy of Formation and Enthalpy of Reaction 257<\/p>\n

3.2 Chemical Kinetics 270<\/p>\n

3.2.1 Fundamental Principles of Chemical Kinetics 270<\/p>\n

3.2.2 Representation of Potential Energy Changes m Reacllons 273<\/p>\n

3.2.3 Reaction Rate Expressions 280<\/p>\n

3.2.4 Examples of Rate Expressions 283<\/p>\n

3.3 General Relationships between Thermodynamic Stability and Reaction Rates 285<\/p>\n

3.3.1 Kinetic versus Thermodynamic Control of Product Composition 285<\/p>\n

3.3.2 Correlations between Thermodynamic and Kinetic Aspects of Reactions 287<\/p>\n

3.3.3 Curtm-Hammett Prmciple 296<\/p>\n

3.4 Electronic Substituent Effects on Reaction Intermediates 297<\/p>\n

3 4.1 Carbocations 300<\/p>\n

3.4.2 Carbanions 307<\/p>\n

3.4 3 Radical Intermediates 311<\/p>\n

3.4.4 Carbonyl Addition Intermediates 319<\/p>\n

3.5 Kinetic Isotope Effects 33<\/p>\n

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