β-디케토네이트-은 착제에 이미다졸-2-이리덴이 배위된 첨가 생성물의 합성 및 특성

정민철; Min Chul Chung

Journal of the Korean Industrial and Engineering Chemistry, Vol.13, No.5, 422-427, August, 2002

Export Citation

β-디케토네이트-은 착제에 이미다졸-2-이리덴이 배위된 첨가 생성물의 합성 및 특성

Synthesis and Characterization of Imidazol-2-ylidene Adducts Silver β-Diketonate Complexes

정민철 ^†

삼성정밀화학연구소 전자재료팀, 대전 305-380

Min Chul Chung^†

Electronics Materials Lab, Samsung Fine Chemical, R&D Center, Daejeon 305-380, Korea

E-mail:

초록

은 착체 화합물들은 silver β-diketonates 착체와 imidazol-2-ylidenes 배위자와의 반응으로부터 합성되었다. 합성된 착체는 1H/13C-NMR, FT-IR, UV, 원소분석을 통해 특성을 파악하였다. 특히 착체 1은 X-ray 결정구조해석을 통해 분자구조를 알 수가 있었다. 결정 데이터: C22H23AgN2O2: Mr = 455.29, Triclinic, space group P-1, a = 7.9671 (11) Å, α = 106.800(15) deg, b = 11.625(2) Å, beta = 93.298(12) deg, c = 12.0479(18) Å, gamma = 105.815(12) deg, V = 1016.4(3) Å(3), Z, = 2, Dc = 1.488 g/cm(3), R1 = 0.1941, wR2 = 0.2438 for 5614 reflections. 얻어진 착체 1의 구조는 단분자이지만 은 원자를 중심으로 두 배위자가 교대로 적중되어 있고, 은 원자와 은 원자간의 거리가 3.000 Å 이다. 그리고 착체의 imidazol-2-ylidene 중 carbenenic 탄소원자의 화학이동은 배위되지 않는 imidazol-2-ylidene 보다 33.3 ~ 38.3 ppm 정도 고자기장쪽으로 이동됨을 알 수가 있었다.

The compounds (β-diketonates)Ag(imidazol-2-ylidenes) were prepared by the reaction of silver β-diketonates with imidazol-2-ylidenes as ligands. These species were characterized by 1H/13C-NMR, FT-IR, UV, elemental analysis. The complex 1 was structurally characterized by X-ray crystallography. Crystal data: C22H23AgN2O2: Mr = 455.29, Triclinic, space group P-1, a = 7.9671(11) Å, α = 106.800 (15) deg, b = 11.625(2) Å, beta = 93.298(12) deg, c = 12.0479(18) Å, gamma = 105.815(12) deg, V = 1016.4(3) Å(3), Z, = 2, Dc = 1.488 g/cm(3), R1 = 0.1941, wR2 = 0.2438 for 5614 reflections. The crystal packing structure in the complex 1 shows the stacked arrangement. The distance between two silver atoms is 3.000 Å. In the 13C-NMR, the peaks of the carbenenic carbon atoms in the complexes are shifted upfield by ca. 33.3 ~ 38.3 ppm.

Keywords:silver;imidazol-2-ylidene;diketonates

[References]

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Edwards DA, Harker RM, Mahon MF, Molloy KC, J. Mater. Chem., 9, 1771 (1999)
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Hurlburt PK, Rack JJ, Dec SF, Anderson OP, Strass SH, Inorg. Chem., 32, 373 (1993)
Arduengo AJ, Dais HVR, Calabrese JC, Davison F, Organometallics, 12, 3405 (1993)
Arduengo AJ, Gamper SF, Calabrese JC, Davidson F, J. Am. Chem. Soc., 116(10), 4391 (1994)
Lin W, Warren TH, Nuzzo RG, Girolami GS, J. Am. Chem. Soc., 115, 11644 (1993)
Yuan Z, Dryden NH, Vittal JJ, Puddephatt RJ, Can. J. Chem., 72, 1605 (1994)
Bailey B, Corbitt TS, Hampden-Smith MJ, Duesler EN, Kodas TT, Polyhedron., 12, 1785 (1993)

[Related Articles]

[1] 2000 SIA (Semiconductor Industry Association) Technology Roadmap, http://public.itrs.net/

[2] Braun AE, Semiconductor Int., 56 (1999)

[3] Peters L, Semiconductor Int., 61 (2000)

[4] Baum TH, Comita PB, The Chemistry of Metal CVD, eds T.T. Kodas and M.J. Hampden-Smith, 310, VCH, Tokyo (1994)

[5] http://www.sfu.ca/chemistry/faculty/Hill/hill.html.

[6] http://www.scienceweb.org/can/pr/n012496.html.

[7] http://www.sfu.ca/vpreserch/Researchlinks/vol_96/photoresist.html.

[8] Arduengo AJ, Harlow RL, Kline M, AAPG Bull., 113, 361 (1991)

[9] U.S. Patent, 5,077,414 (1991)

[10] Arduengo AJ, Dias HVR, Harlow RL, Kline M, J. Am. Chem. Soc., 114, 5530 (1992)

[11] Arduengo AJ, Dias HV, Dixon DA, Harlow RL, Klooster WT, Koetzle TF, J. Am. Chem. Soc., 116(15), 6812 (1994)

[12] Arduengo AJ, Goerlich JR, Marshall WJ, J. Am. Chem. Soc., 117(44), 11027 (1995)

[13] Arduengo AJ, Davidson F, Dias HVR, Goerlich JR, Khasnis D, Marshall WJ, Prakasha TK, J. Am. Chem. Soc., 119(52), 12742 (1997)

[14] Arduengo AJ, Davidson F, Krafczyk R, Marshall WJ, Tamm M, Organometallics, 17, 3375 (1998)

[15] Arduengo AJ, Krafczyk R, Schmutzler R, Tetrahedron, 55, 14523 (1999)

[16] Arduengo AJ, Accounts Chem. Res., 32(11), 913 (1999)

[17] Chung MC, Bull. Korean Chem. Soc., in press (2002)

[18] Kuhn N, Kraz T, Synthesis, 561 (1993)

[19] Wakeshima I, Ohgi H, Kijima I, Synth. React. Inorg. Met. Org. Chem., 23(9), 1507 (1993)

[20] Sheldrick GM, SHELEXL 97. Program for the Refinement of Crystal Structures, University of Gotingen, Germany (1997)

[21] Edwards DA, Harker RM, Mahon MF, Molloy KC, J. Mater. Chem., 9, 1771 (1999)

[22] xu C, Corbitt TS, Hampden-Smith MJ, Kodas TT, Duesler EN, J. Chem. Soc.-Dalton Trans., 2841 (1994)

[23] Hurlburt PK, Rack JJ, Dec SF, Anderson OP, Strass SH, Inorg. Chem., 32, 373 (1993)

[24] Arduengo AJ, Dais HVR, Calabrese JC, Davison F, Organometallics, 12, 3405 (1993)

[25] Arduengo AJ, Gamper SF, Calabrese JC, Davidson F, J. Am. Chem. Soc., 116(10), 4391 (1994)

[26] Lin W, Warren TH, Nuzzo RG, Girolami GS, J. Am. Chem. Soc., 115, 11644 (1993)

[27] Yuan Z, Dryden NH, Vittal JJ, Puddephatt RJ, Can. J. Chem., 72, 1605 (1994)

[28] Bailey B, Corbitt TS, Hampden-Smith MJ, Duesler EN, Kodas TT, Polyhedron., 12, 1785 (1993)