Synthesis and characterization of cyano-substituted carborane-based compounds. Molecular structure of [1-(4-C7H7)-12-(C 5H3-3-(CN)-3,4-(CH3)2)-C 2B10H10]

Jesse Taylor; Wilda Vargas; Ana Torvisco; Karin Ruhlandt-Senge; James T. Spencer

doi:10.1039/c1dt10726g

Synthesis and characterization of cyano-substituted carborane-based compounds. Molecular structure of [1-(4-C₇H₇)-12-(C ₅H₃-3-(CN)-3,4-(CH₃)₂)-C ₂B₁₀H₁₀]

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

3 Scopus citations

Abstract

The reaction of cyanogen chloride with [1-(4-C₇H ₇)-12-(C₅H₃-3,4-(CH₃) ₂)-C₂B₁₀H₁₀] (7) was found to yield two new C₅-substituted carborane cluster-based compounds, [1-(4-C₇H₇)-12-(C₅H₂-3-(CN)-3,4- (CH₃)₂)-C₂B₁₀H₁₀] (8) and [1-(4-C₇H₇)-12-(C₅H-2,4-(CN) ₂-3,4-(CH₃)₂)-C₂B₁₀H 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: C₁₇H₂₅B₁₀N, monoclinic, space group P2₁/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) Å³, Z = 8, R₁ = 0.0729, wR₂ = 0.1464].

Original language	English (US)
Pages (from-to)	10585-10591
Number of pages	7
Journal	Dalton Transactions
Volume	40
Issue number	40
DOIs	https://doi.org/10.1039/c1dt10726g
State	Published - Oct 28 2011

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Inorganic Chemistry

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@article{b98fff78cdeb4f378e07eb1153c85535,

title = "Synthesis and characterization of cyano-substituted carborane-based compounds. Molecular structure of [1-(4-C7H7)-12-(C 5H3-3-(CN)-3,4-(CH3)2)-C 2B10H10]",

abstract = "The reaction of cyanogen chloride with [1-(4-C7H 7)-12-(C5H3-3,4-(CH3) 2)-C2B10H10] (7) was found to yield two new C5-substituted carborane cluster-based compounds, [1-(4-C7H7)-12-(C5H2-3-(CN)-3,4- (CH3)2)-C2B10H10] (8) and [1-(4-C7H7)-12-(C5H-2,4-(CN) 2-3,4-(CH3)2)-C2B10H 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: C17H25B10N, monoclinic, space group P21/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, R1 = 0.0729, wR2 = 0.1464].",

author = "Jesse Taylor and Wilda Vargas and Ana Torvisco and Karin Ruhlandt-Senge and Spencer, {James T.}",

year = "2011",

month = oct,

day = "28",

doi = "10.1039/c1dt10726g",

language = "English (US)",

volume = "40",

pages = "10585--10591",

journal = "Dalton Transactions",

issn = "1477-9226",

publisher = "Royal Society of Chemistry",

number = "40",

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TY - JOUR

T1 - Synthesis and characterization of cyano-substituted carborane-based compounds. Molecular structure of [1-(4-C7H7)-12-(C 5H3-3-(CN)-3,4-(CH3)2)-C 2B10H10]

AU - Taylor, Jesse

AU - Vargas, Wilda

AU - Torvisco, Ana

AU - Ruhlandt-Senge, Karin

AU - Spencer, James T.

PY - 2011/10/28

Y1 - 2011/10/28

N2 - The reaction of cyanogen chloride with [1-(4-C7H 7)-12-(C5H3-3,4-(CH3) 2)-C2B10H10] (7) was found to yield two new C5-substituted carborane cluster-based compounds, [1-(4-C7H7)-12-(C5H2-3-(CN)-3,4- (CH3)2)-C2B10H10] (8) and [1-(4-C7H7)-12-(C5H-2,4-(CN) 2-3,4-(CH3)2)-C2B10H 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: C17H25B10N, monoclinic, space group P21/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) Å3, Z = 8, R1 = 0.0729, wR2 = 0.1464].

AB - The reaction of cyanogen chloride with [1-(4-C7H 7)-12-(C5H3-3,4-(CH3) 2)-C2B10H10] (7) was found to yield two new C5-substituted carborane cluster-based compounds, [1-(4-C7H7)-12-(C5H2-3-(CN)-3,4- (CH3)2)-C2B10H10] (8) and [1-(4-C7H7)-12-(C5H-2,4-(CN) 2-3,4-(CH3)2)-C2B10H 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: C17H25B10N, monoclinic, space group P21/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) Å3, Z = 8, R1 = 0.0729, wR2 = 0.1464].

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U2 - 10.1039/c1dt10726g

DO - 10.1039/c1dt10726g

M3 - Article

C2 - 21946806

AN - SCOPUS:80053475361

SN - 1477-9226

VL - 40

SP - 10585

EP - 10591

JO - Dalton Transactions

JF - Dalton Transactions

IS - 40

ER -

Synthesis and characterization of cyano-substituted carborane-based compounds. Molecular structure of [1-(4-C₇H₇)-12-(C ₅H₃-3-(CN)-3,4-(CH₃)₂)-C ₂B₁₀H₁₀]

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