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      13C NMR-Study of 1,1-Dipotassio-2,3,4,5-Tetraphenyl-1-Silacyclopentadienide Dianion [SiC4Ph4]2−•2[K+] and 1,1-Dipotassio-2,3,4,5-Tetraphenyl-1- Germacyclopentadienide Dianion [GeC4Ph4]2−•2[K+]

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      https://www.riss.kr/link?id=A105942842

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      다국어 초록 (Multilingual Abstract)

      The chemical shifts in the 13C NMR spectra of 2,3,4,5-tetraphenyl-1-silacyclopentdienide dianion [SiC4Ph4]2−•2[K+] (3) and 2,3,4,5-tetraphenyl-1-germacyclopentdienide dianion [GeC4Ph4]2−•2[K+] (4) were compared to those of [SiC4Ph4]2−•2[Li+] (5), [SiC4Ph4]2−•2[Na+] (6), and [GeC4Ph4]2−•2[Li+] (7). The average polarizations in two phenyl groups of two potassium salts are decreased over 15% to 20% comparing to those of the lithium salts and sodium salt {[EC4Ph4]2−•2[M+] (E=Si, Ge, M=Li, Na) due to the effect of the counter potassium cation.
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      The chemical shifts in the 13C NMR spectra of 2,3,4,5-tetraphenyl-1-silacyclopentdienide dianion [SiC4Ph4]2−•2[K+] (3) and 2,3,4,5-tetraphenyl-1-germacyclopentdienide dianion [GeC4Ph4]2−•2[K+] (4) were compared to those of [SiC4Ph4]2−•2[Li...

      The chemical shifts in the 13C NMR spectra of 2,3,4,5-tetraphenyl-1-silacyclopentdienide dianion [SiC4Ph4]2−•2[K+] (3) and 2,3,4,5-tetraphenyl-1-germacyclopentdienide dianion [GeC4Ph4]2−•2[K+] (4) were compared to those of [SiC4Ph4]2−•2[Li+] (5), [SiC4Ph4]2−•2[Na+] (6), and [GeC4Ph4]2−•2[Li+] (7). The average polarizations in two phenyl groups of two potassium salts are decreased over 15% to 20% comparing to those of the lithium salts and sodium salt {[EC4Ph4]2−•2[M+] (E=Si, Ge, M=Li, Na) due to the effect of the counter potassium cation.

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      참고문헌 (Reference)

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      2 M. Saito, "The aromaticity of the stannole dianion" 44 : 6553-6556, 2005

      3 M. Saito, "The anions and dianions of group 14 metalloles" 249 : 765-780, 2005

      4 D. A. Dougherty, "The Cation-π Interaction" 46 : 885-893, 2013

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      7 W. P. Freeeman, "Synthesis and study of cyclic π-Systems containing silicon and germanium. The question of aromaticity in cyclopentadienyl analogues" 118 : 10457-10468, 1996

      8 W. -C. Joo, "Synthesis and reactivity of 1, 1, -disodio-2, 3, 4, 5-tetraphenyl-1-silacyclopentadiene" 391 : 27-36, 1990

      9 J. -H. Hong, "Synthesis and characterization of two aromatic siliconcontaining dianions : The 2, 3, 4, 5-tetraphenylsilole dianion and the 1, 1’-disila-2, 2’, 3, 3’, 4, 4’, 5, 5’-octaphenylfulvalene dianion" 13 : 3387-3389, 1994

      10 J.-H. Hong, "Synthesis and characterization of a novel pentavalent silane: 1-Methyl-1,1-dihydrido-2,3,4,5-tetraphenyl-1-silacyclopentadiene silicate, [Ph4C4SiMeH2-]·[K +]" 14 : 574-576, 1995

      1 S. -B. Choi, "Unique Bis-η5/η1 bonding in a dianionic germole. Synthesis and structural characterization of the dilithium salt of the 2, 3, 4, 5-tetramethyl germole dianion" 18 : 2919-2921, 1999

      2 M. Saito, "The aromaticity of the stannole dianion" 44 : 6553-6556, 2005

      3 M. Saito, "The anions and dianions of group 14 metalloles" 249 : 765-780, 2005

      4 D. A. Dougherty, "The Cation-π Interaction" 46 : 885-893, 2013

      5 D. H. O'Brien, "Tetraanion of 1, 1-dimethyl-2, 3, 4, 5-tetraphenyl-1-silacyclopentadiene" 103 : 3237-3239, 1981

      6 U. Bankwitz, "Synthesis, solid-state structure, and reduction of 1, 1-dichloro-2, 3, 4, 5-tetramethylsilole" 499 : C7-C9, 1995

      7 W. P. Freeeman, "Synthesis and study of cyclic π-Systems containing silicon and germanium. The question of aromaticity in cyclopentadienyl analogues" 118 : 10457-10468, 1996

      8 W. -C. Joo, "Synthesis and reactivity of 1, 1, -disodio-2, 3, 4, 5-tetraphenyl-1-silacyclopentadiene" 391 : 27-36, 1990

      9 J. -H. Hong, "Synthesis and characterization of two aromatic siliconcontaining dianions : The 2, 3, 4, 5-tetraphenylsilole dianion and the 1, 1’-disila-2, 2’, 3, 3’, 4, 4’, 5, 5’-octaphenylfulvalene dianion" 13 : 3387-3389, 1994

      10 J.-H. Hong, "Synthesis and characterization of a novel pentavalent silane: 1-Methyl-1,1-dihydrido-2,3,4,5-tetraphenyl-1-silacyclopentadiene silicate, [Ph4C4SiMeH2-]·[K +]" 14 : 574-576, 1995

      11 J. -H. Hong, "Synthesis and characterization of a delocalized germanium-containing dianion : dilithio-2, 3, 4, 5-tetraphenyl-germole" 132 : 495-498, 1995

      12 J. -H. Hong, "Synthesis and NMR-study of the 2, 3, 4, 5-tetraethylsilole dianion [SiC4Et4]2−•2[Li]+" 16 : 8033-8040, 2011

      13 J. -H. Hong, "Synthesis and NMR-study of 1-trimethylsilyl substituted silole anion [Ph4C4Si(SiMe3)]−•[Li]+and 3-silolenide 2,5-carbodianions {[Ph4C4Si(n-Bu)2]−2•2[Li]+, [Ph4C4Si(t-Bu)2]−2•2[Li]+} via silole dianion [Ph4C4Si]−2•2[Li]+" 18 : 10568-10579, 2013

      14 C. Fekete, "Synthesis and NMR characterization of 2, 5-bis(Trimethylsilyl)-3, 4-diphenyl-1-silacyclopentadienyl dianion" 189 : 1076-1083, 2014

      15 Y. Pan Y, "Surprising reaction of non-nucleophilic bases with 1-hydrosiloles: Addition and not deprotonation" 16 : 1445-1451, 1997

      16 C. Fekete, "Substituent effect on the aromaticity of the silolide anion" 25 : 377-387, 2014

      17 S. Kim, "Structures, energetics, and aromaticities of the tetrasilacyclobutadiene dianion and related compounds: (Si4H4)2–, (Si4H4)2–·2Li+, [Si4(SiH3)4]2–·2Li+, [Si4(SiH3)4]2–·2Na+, and [Si4(SiH3)4]2–·2K+" 115 : 5478-5487, 2011

      18 V. Y. Lee, "Stable aromatic compounds containing heavier group 14 elements" 611 : 228-235, 2000

      19 W. P. Freeman, "Siloyl anions and silole dianions : Structure of [K(crown-6)+]2[C4Me4Si2-]" 35 : 882-884, 1996

      20 T. Wakahara, "Reaction of hydrosilanes with lithium. formation of silole anions from 1-methylsilole via carbodianion" 26 : 1179-1180, 1997

      21 N. A. Troitski, "NMR study of 1-hydro-2,3,4,5-tetraphenylsilole derivatives" 24 : 1-4, 2001

      22 L. Aubouy, "Molecular engineering to improve the charge carrier balance in single-layer silole-based OLEDs" 33 : 1290-1300, 2009

      23 M. Hissler, "Linear organic π-conjugated systems featuring the heavy group 14and 15 elements" 244 : 1-44, 2003

      24 V. Y. Lee, "Heavy analogues of the 6p-electron anionic ring systems : Cyclopentadienide ion and cyclobutadiene dianion" 692 : 2800-2810, 2007

      25 H. Grützmacher, "Five-membered aromatic and antianromatic rings with gallium, germanium, and bismuth centers : A short march through the periodic table" 34 : 295-298, 2005

      26 S. N. Tandura, "Electron density distributions in substituted 2, 3, 4, 5-tetraphenyl-1-germacyclopenta-2, 4-dienes studied by NMR spectroscopy" 46 : 1859-1861, 1997

      27 X. Zhan, "Electron affinities of 1, 1-diaryl-2, 3, 4, 5-tetraphenylsiloles:direct measurements and comparison with experimental and theoretical estimates" 127 : 9021-9029, 2005

      28 J. -H. Hong, "Dissociation of the disilatricyclic diallylic dianion [(C4Ph4SiMe)2]−2 to the silole anion [MeSiC4Ph4]− by halide ion coordination or halide ion nucleophilic substitution at the silicon atom" 16 : 8451-8462, 2011

      29 H. Sohn, "Dimerization of the Silole Anion [C4Ph4-SiMe]− to a Tricyclic Diallylic Dianion" 16 : 2770-2772, 1997

      30 R. West, "Dilithium derivative of tetraphenylsilole : An η1-η5 dilithium" 117 : 11608-11609, 1995

      31 R. West, "Dianion of tetraphenylgermole is aromatic" 35 : 1002-1004, 1996

      32 S. N. Tandura, "Correlation NMR spectroscopy of 1,1-dichloro-2,3,4,5-tetraphenyl-1-germacyclopenta-2,4-diene" 46 : 602-604, 1997

      33 S. N. Tandura, "Charge localization in the dianion of tetraphenylgermole according to 13C NMR data" 22 : 9-14, 1999

      34 M. Saito, "Challenge to expand the concept of aromaticity to tin-and lead-containing carbocyclic compounds : Synthesis, structures and reactions of dilithiostannoles and dilithioplumbole" 256 : 627-636, 2012

      35 V. Y. Lee, "Aromaticity of group 14 organometallics : Experimental aspects" 46 : 6596-6620, 2007

      36 B. Goldfuss, "Aromaticity in silole dianions : Structural, energetic, and magnetic aspects" 15 : 1755-1757, 1996

      37 B. Goldfuss, "Aromaticity in group 14 metalloles : Structural, energetic, and magnetic criteria" 16 : 1543-1552, 1997

      38 W. J. Hehre, "Ab initio calculations of charge distributions in monosubstituted benzenes and in meta-and para-substituted fluorobenzenes. comparison with 1H, 13C, and 19F NMR substituent shifts" 12 : 159-187, 1976

      39 J. -H. Hong, "A stable aromatic species containing silicon. Synthesis and characterization of 1-t-butyl-2, 3, 4, 5-tetraphenyl-1-silacyclopentadienide anion" 115 : 5883-5884, 1993

      40 J. -H. Hong, "A novel lithocenophane derivative of a trisgermole dianion : [Li(thf)(tmeda)][2, 3, 4, 5-Et4-Ge, Ge-{Li(2, 3, 4, 5-Et4C4Ge)2} C4Ge]" 35 : 186-188, 1996

      41 S. N. Tandura, "13C NMR study of 2,3,4,5-tetraphenylsilole dilithium salt" 48 : 214-217, 1999

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