Synthesis and characterization of cyano-substituted carborane-based compounds. Molecular structure of [1-(4-C 7H 7)-12-(C 5H 3-3-(CN)-3,4-(CH 3) 2)-C 2B 10H 10]

Jesse Taylor, Wilda Vargas, Ana Torvisco, Karin Ruhlandt, James T Spencer

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Abstract

The reaction of cyanogen chloride with [1-(4-C 7H 7)-12-(C 5H 3-3,4-(CH 3) 2)-C 2B 10H 10] (7) was found to yield two new C 5-substituted carborane cluster-based compounds, [1-(4-C 7H 7)-12-(C 5H 2-3-(CN)-3,4- (CH 3) 2)-C 2B 10H 10] (8) and [1-(4-C 7H 7)-12-(C 5H-2,4-(CN) 2-3,4-(CH 3) 2)-C 2B 10H 10] (9). This cyano-substitution pattern is in contrast to the known substitution for the analogous organic quinarene[5.6.7] system. The observed unique cluster-based products may be understood by a combination of steric and electronic effects. Compounds 8 and 9 were characterized by complete multinuclear NMR, 1H- 1H COSY NMR, 1H- 13C HMQC NMR, FTIR, UV-Vis, IR, MS data and a single crystal analysis for 8 [X-ray data for 8: C 17H 25B 10N, monoclinic, space group P2 1/n with cell constants a = 8.6794(17) Å, b = 11.021(2) Å, c = 43.175(9) Å, β = 91.00(3)°, V = 4129.2(14) Å 3, Z = 8, R 1 = 0.0729, wR 2 = 0.1464].

Original languageEnglish (US)
Pages (from-to)10585-10591
Number of pages7
JournalDalton Transactions
Volume40
Issue number40
DOIs
StatePublished - Oct 28 2011

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Molecular structure
Nuclear magnetic resonance
Substitution reactions
Single crystals
X rays
vitamin B 12 factor III
crystal-8
cyanogen chloride

ASJC Scopus subject areas

  • Inorganic Chemistry

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Synthesis and characterization of cyano-substituted carborane-based compounds. Molecular structure of [1-(4-C 7H 7)-12-(C 5H 3-3-(CN)-3,4-(CH 3) 2)-C 2B 10H 10]. / Taylor, Jesse; Vargas, Wilda; Torvisco, Ana; Ruhlandt, Karin; Spencer, James T.

In: Dalton Transactions, Vol. 40, No. 40, 28.10.2011, p. 10585-10591.

Research output: Contribution to journalArticle

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title = "Synthesis and characterization of cyano-substituted carborane-based compounds. Molecular structure of [1-(4-C 7H 7)-12-(C 5H 3-3-(CN)-3,4-(CH 3) 2)-C 2B 10H 10]",
abstract = "The reaction of cyanogen chloride with [1-(4-C 7H 7)-12-(C 5H 3-3,4-(CH 3) 2)-C 2B 10H 10] (7) was found to yield two new C 5-substituted carborane cluster-based compounds, [1-(4-C 7H 7)-12-(C 5H 2-3-(CN)-3,4- (CH 3) 2)-C 2B 10H 10] (8) and [1-(4-C 7H 7)-12-(C 5H-2,4-(CN) 2-3,4-(CH 3) 2)-C 2B 10H 10] (9). This cyano-substitution pattern is in contrast to the known substitution for the analogous organic quinarene[5.6.7] system. The observed unique cluster-based products may be understood by a combination of steric and electronic effects. Compounds 8 and 9 were characterized by complete multinuclear NMR, 1H- 1H COSY NMR, 1H- 13C HMQC NMR, FTIR, UV-Vis, IR, MS data and a single crystal analysis for 8 [X-ray data for 8: C 17H 25B 10N, monoclinic, space group P2 1/n with cell constants a = 8.6794(17) {\AA}, b = 11.021(2) {\AA}, c = 43.175(9) {\AA}, β = 91.00(3)°, V = 4129.2(14) {\AA} 3, Z = 8, R 1 = 0.0729, wR 2 = 0.1464].",
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T1 - Synthesis and characterization of cyano-substituted carborane-based compounds. Molecular structure of [1-(4-C 7H 7)-12-(C 5H 3-3-(CN)-3,4-(CH 3) 2)-C 2B 10H 10]

AU - Taylor, Jesse

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AU - Spencer, James T

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N2 - The reaction of cyanogen chloride with [1-(4-C 7H 7)-12-(C 5H 3-3,4-(CH 3) 2)-C 2B 10H 10] (7) was found to yield two new C 5-substituted carborane cluster-based compounds, [1-(4-C 7H 7)-12-(C 5H 2-3-(CN)-3,4- (CH 3) 2)-C 2B 10H 10] (8) and [1-(4-C 7H 7)-12-(C 5H-2,4-(CN) 2-3,4-(CH 3) 2)-C 2B 10H 10] (9). This cyano-substitution pattern is in contrast to the known substitution for the analogous organic quinarene[5.6.7] system. The observed unique cluster-based products may be understood by a combination of steric and electronic effects. Compounds 8 and 9 were characterized by complete multinuclear NMR, 1H- 1H COSY NMR, 1H- 13C HMQC NMR, FTIR, UV-Vis, IR, MS data and a single crystal analysis for 8 [X-ray data for 8: C 17H 25B 10N, monoclinic, space group P2 1/n with cell constants a = 8.6794(17) Å, b = 11.021(2) Å, c = 43.175(9) Å, β = 91.00(3)°, V = 4129.2(14) Å 3, Z = 8, R 1 = 0.0729, wR 2 = 0.1464].

AB - The reaction of cyanogen chloride with [1-(4-C 7H 7)-12-(C 5H 3-3,4-(CH 3) 2)-C 2B 10H 10] (7) was found to yield two new C 5-substituted carborane cluster-based compounds, [1-(4-C 7H 7)-12-(C 5H 2-3-(CN)-3,4- (CH 3) 2)-C 2B 10H 10] (8) and [1-(4-C 7H 7)-12-(C 5H-2,4-(CN) 2-3,4-(CH 3) 2)-C 2B 10H 10] (9). This cyano-substitution pattern is in contrast to the known substitution for the analogous organic quinarene[5.6.7] system. The observed unique cluster-based products may be understood by a combination of steric and electronic effects. Compounds 8 and 9 were characterized by complete multinuclear NMR, 1H- 1H COSY NMR, 1H- 13C HMQC NMR, FTIR, UV-Vis, IR, MS data and a single crystal analysis for 8 [X-ray data for 8: C 17H 25B 10N, monoclinic, space group P2 1/n with cell constants a = 8.6794(17) Å, b = 11.021(2) Å, c = 43.175(9) Å, β = 91.00(3)°, V = 4129.2(14) Å 3, Z = 8, R 1 = 0.0729, wR 2 = 0.1464].

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