咪唑（imidazole）的雜環化合物(1)可利用其不接氫的氮原子作配位基。其氫原子轉移異構物(2)是含氮雜環次烯基化合物（N－Heterocyclic Carbene）。在1990年代中期開始被發現它可以扮演一個相當有效的有機金屬配位基1。本論文在於探討它們和各種路易士酸之間酸鹼作用能量大小酸類。包括BR3，CR3+，AlR3，SiR3+，NR2+，PR2+，O，S (R=氫，鹵素)等。我們感興趣的問題是兩者和酸作用的相對強度，又(2)雖然較(1)不穩定，但親核性較強，我們想知道何種酸使得鍵結物的相對穩定性順序相反於原先異構物。

我們也探討兩雜環的相關系統，如上述參鍵小分子(HCN，HNC)及雙鍵次烯基系統如methylenimine（H2CNH）、aminocarbene（H2NCH）等。我們是以密度函數理論（DFT）進行理論計算，選用B3LYP/6-311++G**的方法及基底函數，是用Gaussian98軟體。
我們擬探討何種酸會扭轉鍵結物的相對穩定性，相反於原先異構物。即原先△E0＝E(1)－E(2)約為-28.4kcal/mol，接上路易士酸的複合物為1΄及2΄，則ΔE＝E(1΄)－E(2΄)是否會大於零。例如以H＋為路易士酸，ΔE為零，1΄及2΄是相同的一鍵結物。其實和酸作用的能量差距ΔBE（ΔE－ΔE。）也是一個有興趣的量。ΔBE＞0表示(2)中的碳的親核性大於(1)中的氮，大部分酸會顯示ΔBE＞0之結果。我們將此系統由碳次烯基系統延伸到矽次烯基的系統，即探討此系統與其異構物與不同路易士酸鍵結的情況。
同樣，我們也將我們的研究延伸到含矽雙鍵小分子系統，如silanimine (H2SiNH)、aminosilylene (HSiNH2)，我們將這些化合物和各種路易士酸之間酸鹼作用。我們將把小分子異構物和雜環分子異構物計算結果分別就碳、矽兩類做比較，並探討其間關聯性。

1.Robert H. Crabtree 〝Carbenes. Pincers, chelates, and abnormal bindind modes,〞 Pure Appl. Chem. 2003, 75, No. 4, 435
2.Levine, I. N. 〝Quantum Chemistry〞5th., Prentice Hall International, Inc., 1997.
3.Bourissou, D.; Guerret, O.; Gabbai, F. P.; Bertrand, G. 〝Stable Carbene, 〞 Chem. Rev. 2000, 100, 39
4.Regitz; Maas Diazo Compound; Academic Press: New York, 1986, 170
5.H. W. Wanzlick, 〝Aspects of Nucleophilic Carbene Chemistry,〞 Angew. Chem. Int. Ed. Engl. 1962, 1, 75
6.E. O. Fisher; Maasböl, A. Angew. Chem. Int. Ed. Engl. , 1964, 3, 580
7.H. W. Wanzlick, H. J. Schonherr, Liebigs Ann. Chem. 1970, 731, 176
8.H. J. Schonherr, H. W. Wanzlick, Chem. Ber. 1970, 103, 1037
9.A. J. Arduengo, D. A. Dixon, K. D. Dobss, J. Am. Chem. Soc. 1991, 113, 6463
10.A. J. Arduengo, R. L. Harlow, M. Kline, J. Am. Chem. Soc. 1991, 113, 361
11.W. Kirmse: Carbene, Carbenoide and Carbenanaloge, Verlag Chemie, Weinheim, 1969, p. 6ff
12.W. Kirmse: Carbene Chemistry, 2nd ed. , Academic press, New York 1971
13.M. Jones, R. A. Moss: Carbene I, Wiley, New York 1973
14.M. Jones, R. A. Moss: Carbene Ⅱ, Wiley, New York 1975
15.A. J. Arduengo, III, H. V. Rasika Dias, David A. Dixon, Richard L. Harlow, W. T. Klooster, T. F. Koetzle, 〝Electron Distribution in a Stable Carbene,〞 J. Am. Chem. Soc. , 1994, 116, 6812
16.D. DiXon, A. J., III. J. Phys. Chem. 1991, 95, 4180
17.G. Sini, O. Eisenstein, R. H. Crabtree, 〝Preferential C-Binding versus N-Binding in Imidazole Depends on the Metal Fragment Involved, 〞 Inorg. Chem., 2002, 41, 602
18.C. Heinemann, W. Thiel Chem Phys. Lett. 1994, 217, 11
19.A. Graham McGibbon, Christoph Heinemann, David J. Lavorato, Helmut Schwarz, 〝Imidazol-2-ylidene: Generation of a Missing Carbene and Its Dication by Neutralization-Reionizatin and Charge-Stripping Mass Spectrometry, 〞 Angew. Chem. Int. Ed. Engl. 1997, 36, 1478
20.Jonas Volker, Frenking Gernot, T. Reetz Manfred, 〝Comparative Theoretical Study of Lewis Acid-Base Complexes of BH3, BF3, BCl3, AlCl3, and SO2, 〞 J. Am. Chem. Soc. 1994, 116, 8741
21.G. N. Lewis, Valence and the Structure of Atoms and Molecules; The Chemical Catalog Co., Inc.: New York, 1923
22.E. O. Fischer, A Maasbol, Angew. Chem. Int. Ed. Engl. 1964, 76, 645
23.K. Ofele, J. Organomet. Chem. 1968, 12,42
24.W. A. Herrmann, C. Kocher, Angew. Chem. Int. Ed Engl. 1997, 36, 2126
25.A. J. Arduengo, H. V. R. Dias, J. C. Calabrese, J. Am. Chem. Soc. 1992, 114, 9724
26.N. Kuhn, G. Henkel, T. Krate, J. Kreutzberg, R. Boese, A. H. Maulitz, Chem. Ber., 1993, 126, 2041
27.A. J. III Arduengo, Siegfried F. Gamper, Matthias Tamm, Joseph C. Calabrese, Frederic Davidson, Hugh A. Craig, J. Am. Chem. Soc. 1995, 117, 572
28.W. A. Herrmann, O. Runte, G. R. J. Artus, J. Organomet. Chem., 1995, 501, C1
29.A. J. Arduengo, H. V. R. Dias, F. Davidson, R. L. Harlow, J. Organomet. Chem., 1993, 462, 13
30.O. Runte, Dissertation, Technische Universitat Munchen, 1997.
31.N. Kuhn, H. Bohnen, J. Kreutzberg, D. Blaser, R. Boese, J. Chem. Soc. Chem. Commun., 1993, 1136
32.N. Kuhn, T. Kratz, D. Blaser, R. Boese, Chem. Ber., 1995, 128, 245
33.A. Wolfgang, Herrmann, Elison Martina, Fischer Jakob, Köcher Christian, R. J. Artus Georg, Angew. Chem. Int. Ed. Engl. 1995, 34, 2371
34.Applied Homogeneous Catalysis with Organometallic Complexes（Eds.：B. Cornils, W. A. Herrmann）, VCH, Weinheim, 1996
35.R. H. Grubbs in Comprehensive Organometallic Chemistry, Vol 8（Eds.：G. Wilkinson, F. G. A. Stone, E. W. Abel）, Pergamon, Oxford, 1982, p.499.
36.M. Brookhart, W. B. Studabaker, Chem. Rev. 1987, 87, 411.
37.K. H. Dotz in Organometallics in Organic Synthesis（Eds,：A de Meijere. H. Tom Dieck）, Springer, Berlin, 1998.
38.Ch. Aubauer, T.M. Klapötke, A. Schulz, J. Mol. Struct. (Theochem), 2001, 543, 285
39.F. Bessac, G. Frenking, Inorg. Chem. 2003, 42, 7990
40.Siberberg, Chemistry－The Molecular Nature of Matter and Change, 1996, Mosby－Year Book, Inc.
41.P. P. Gaspar, React. React. Intermed. 1981, 2, 335
42.W. P. Neumann, Nachr. Chem. Tech. Lab. 1982, 30, 190
43.G. Maier, H. P. Peisenauer, K. Schoettler, J. Organomet. Chem. 1989, 366, 25
44.G. Raabe, J. J. Michl, Chem. Rev. 1985, 85,419
45.M. Veith, E. Wele, R. Lisowsky, R. Loppe, H. Schno ckel, Chem. Ber. 1992, 125,1375
46.G. R. Gillette, G. Noren, R. West, Organometallics. 1990, 9, 2925
47.W. Sander, A. Patyk, G. Bucher, J. Mol. Struct. 1990, 222, 21
48.G. Maier, J. Glatthaar, H. P. Reisenauer, Chem. Ber. 1989, 122,2403
49.M. Denk, R. West, R. Hayashi, Silylenes, Stable and Unstable in Organosilicon Chemistry. VCH. Weinherim. 1995, p.251
50.R. Okazaki, N. Tokitoh, Acc. Chem. Res. 2000, 33,625
51.N. Tokitoh, T. Matsumoto, R. Okazaki, Bull. Chem. Soc. Jpn. 1999, 72, 1665
52.Auner N., Weis J. In Organosilicon Chemistry IV; VCH：Weinheim, Germany, 2000
53.C. Heinemann, W. Thiel, Chem. Phys. Lett. 1994, 217, 11
54.C. Bohme, G. Frenking, J. Am. Chem. Soc. 1996, 118, 2039
55.A. J. Arduengo, H. Bock, H. Chen, M. Denk, D. A. Dixon, J. C. Green, W. A. Herrmann, N. L. Jones, M. Wagner, R. West, J. Am. Chem. Soc. 1994, 116, 6641
56.Su Ming Der, Chu San Yan, Inorg. Chem. 1999, 38, 4819
57.V. A. Basiuk, J. Phys. Chem. A. 2001, 105, 4252
58.V. A. Basiuk, Bogillo VI, ADV SPACE RES., 2002, 30(6), 1445
59.Petrie, S. J. Phys. Chem. A, 2002, 106, 11181
60.Yitzhak Apeloig, Karsten Albrecht, J. Am. Chem. Soc.; 1995, 117, 7263
61.Liao, H. Y.; Chu, S. Y., Int. J. Quantum Chem., 2002, 41, 1320
62.C. J. Carmalt and A. H. Cowley, Adv. Inorg. Chem., 2000, 50, 1
63.N. Kuhn, H. Bohnen, J. Kreutzberg, D. Bläser and R. Boese, J. Chem. Soc. Chem. Commun. , 1993, 1136
64.Arduengo, A. J., III; Davidson, F.; Dias, H. V. R.; Goerlich, J. R.; Khasnis, D.; Marshall, W. J.; Prakasha, T. K.; J. Am. Chem. Soc. , 1997, 119, 12742
65.W. M. Boesveld, B. Gehrhus, P. B. Hitchcock, M. F. Lappert and P. v. R. Schleyer, Chem. Commun. , 1993, 32, 1541
66.C. Glidewell, H. D. Holden and D. C. Liles, J. Mol. Struct. , 1980, 66, 325
67.Dieter Enders, Klaus Breuer, Gerhard Raabe, Jan Runsink, J. Henrique Teles, Johann-Peter Melder, Klaus Ebel, Stefan Brode, Angew. Chem. Int. Ed. Engl. 1995, 34, 1021
68.G. B. Ansell, D. M. Forkey and D. W. Moore, J. Chem. Soc. Chem. Commun. , 1970, 56
69.G. B. Ansell, J. Chem. Soc., Perkin Trans. 2, 1972, 841
70.Gilles Frison, Alain Sevin, J. Chem. Soc., Perkin Trans. 2, 2002, 16
71.L. Paulin：The Nature of the Chemical Bond. 3rd Ed., Cornell University Press, Ithaca, NY 1960