Synthesis of aluminum alkoxide and bis-alkoxide compounds containing bidentate pyrrolyl ligands

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Abstract

A series of aluminum alkoxide and bis-alkoxides compounds were synthesized and characterized. Reacting 1 with 1 and 2 equiv. of t-butanol in methylene chloride generates [C4H3N(CH2NMe2)-2]2Al(O-t-Bu) (2) and [C4H3N(CH2NMe2)-2-H-C4H3N(CH2NMe2)-2]Al(O-t-Bu)2 (3) in 47% and 54% yield, respectively. The 1H NMR spectrum of 2 exhibits two singlets for NMe2 and CH2N at δ 2.52 and 3.84, respectively, representing the symmetrical manner of molecular structure 2 in a solution. Compound 3 is not thermal stable in solution which decompose into substituted pyrrole ligand C4H4N(CH2NMe2)-2 and unknown aluminum alkoxides. Reacting 1 with 2 equiv. of triphenylsilanol in methylene chloride generates a tetra-coordinated aluminum "ate" compound [C4H3N(CH2NMe2)-2-H- C4H3N(CH2NMe2)-2]Al(OSiPh3)2 (4) in 49% yield. The 1H NMR spectra of 4 at room temperature show a broad signal at δ 1.57 for NMe2 fragments and the signals for CH2N were not observed. VT 1H NMR spectra of 4 show the NMe2 fragments became two singlets (δ 1.27 and 2.12) and the CH2N exhibited two doublets (δ 2.44 and 3.56) at 240 K. The fluxional energy barrier (ΔG) is estimated at ca. 50 kJ/mol. The molecular structures of compounds 3 and 4 are determined by single-crystal X-ray diffractometer.

Original languageEnglish
Pages (from-to)3718-3722
Number of pages5
JournalJournal of Organometallic Chemistry
Volume692
Issue number17
DOIs
Publication statusPublished - 2007 Aug 1

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alkoxides
Aluminum
Methylene Chloride
Ligands
Dichloromethane
Nuclear magnetic resonance
Molecular Structure
aluminum
methylene
nuclear magnetic resonance
Molecular structure
ligands
Aluminum Compounds
molecular structure
synthesis
chlorides
Aluminum compounds
aluminum compounds
tert-Butyl Alcohol
fragments

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

Cite this

@article{d906d37263f04d15bcde89a81e0fdd90,
title = "Synthesis of aluminum alkoxide and bis-alkoxide compounds containing bidentate pyrrolyl ligands",
abstract = "A series of aluminum alkoxide and bis-alkoxides compounds were synthesized and characterized. Reacting 1 with 1 and 2 equiv. of t-butanol in methylene chloride generates [C4H3N(CH2NMe2)-2]2Al(O-t-Bu) (2) and [C4H3N(CH2NMe2)-2-H-C4H3N(CH2NMe2)-2]Al(O-t-Bu)2 (3) in 47{\%} and 54{\%} yield, respectively. The 1H NMR spectrum of 2 exhibits two singlets for NMe2 and CH2N at δ 2.52 and 3.84, respectively, representing the symmetrical manner of molecular structure 2 in a solution. Compound 3 is not thermal stable in solution which decompose into substituted pyrrole ligand C4H4N(CH2NMe2)-2 and unknown aluminum alkoxides. Reacting 1 with 2 equiv. of triphenylsilanol in methylene chloride generates a tetra-coordinated aluminum {"}ate{"} compound [C4H3N(CH2NMe2)-2-H- C4H3N(CH2NMe2)-2]Al(OSiPh3)2 (4) in 49{\%} yield. The 1H NMR spectra of 4 at room temperature show a broad signal at δ 1.57 for NMe2 fragments and the signals for CH2N were not observed. VT 1H NMR spectra of 4 show the NMe2 fragments became two singlets (δ 1.27 and 2.12) and the CH2N exhibited two doublets (δ 2.44 and 3.56) at 240 K. The fluxional energy barrier (ΔG‡) is estimated at ca. 50 kJ/mol. The molecular structures of compounds 3 and 4 are determined by single-crystal X-ray diffractometer.",
author = "Lin, {Che Yu} and Lee, {Hon Man} and Jui-Hsien Huang",
year = "2007",
month = "8",
day = "1",
doi = "10.1016/j.jorganchem.2007.05.013",
language = "English",
volume = "692",
pages = "3718--3722",
journal = "Journal of Organometallic Chemistry",
issn = "0022-328X",
publisher = "Elsevier",
number = "17",

}

Synthesis of aluminum alkoxide and bis-alkoxide compounds containing bidentate pyrrolyl ligands. / Lin, Che Yu; Lee, Hon Man; Huang, Jui-Hsien.

In: Journal of Organometallic Chemistry, Vol. 692, No. 17, 01.08.2007, p. 3718-3722.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis of aluminum alkoxide and bis-alkoxide compounds containing bidentate pyrrolyl ligands

AU - Lin, Che Yu

AU - Lee, Hon Man

AU - Huang, Jui-Hsien

PY - 2007/8/1

Y1 - 2007/8/1

N2 - A series of aluminum alkoxide and bis-alkoxides compounds were synthesized and characterized. Reacting 1 with 1 and 2 equiv. of t-butanol in methylene chloride generates [C4H3N(CH2NMe2)-2]2Al(O-t-Bu) (2) and [C4H3N(CH2NMe2)-2-H-C4H3N(CH2NMe2)-2]Al(O-t-Bu)2 (3) in 47% and 54% yield, respectively. The 1H NMR spectrum of 2 exhibits two singlets for NMe2 and CH2N at δ 2.52 and 3.84, respectively, representing the symmetrical manner of molecular structure 2 in a solution. Compound 3 is not thermal stable in solution which decompose into substituted pyrrole ligand C4H4N(CH2NMe2)-2 and unknown aluminum alkoxides. Reacting 1 with 2 equiv. of triphenylsilanol in methylene chloride generates a tetra-coordinated aluminum "ate" compound [C4H3N(CH2NMe2)-2-H- C4H3N(CH2NMe2)-2]Al(OSiPh3)2 (4) in 49% yield. The 1H NMR spectra of 4 at room temperature show a broad signal at δ 1.57 for NMe2 fragments and the signals for CH2N were not observed. VT 1H NMR spectra of 4 show the NMe2 fragments became two singlets (δ 1.27 and 2.12) and the CH2N exhibited two doublets (δ 2.44 and 3.56) at 240 K. The fluxional energy barrier (ΔG‡) is estimated at ca. 50 kJ/mol. The molecular structures of compounds 3 and 4 are determined by single-crystal X-ray diffractometer.

AB - A series of aluminum alkoxide and bis-alkoxides compounds were synthesized and characterized. Reacting 1 with 1 and 2 equiv. of t-butanol in methylene chloride generates [C4H3N(CH2NMe2)-2]2Al(O-t-Bu) (2) and [C4H3N(CH2NMe2)-2-H-C4H3N(CH2NMe2)-2]Al(O-t-Bu)2 (3) in 47% and 54% yield, respectively. The 1H NMR spectrum of 2 exhibits two singlets for NMe2 and CH2N at δ 2.52 and 3.84, respectively, representing the symmetrical manner of molecular structure 2 in a solution. Compound 3 is not thermal stable in solution which decompose into substituted pyrrole ligand C4H4N(CH2NMe2)-2 and unknown aluminum alkoxides. Reacting 1 with 2 equiv. of triphenylsilanol in methylene chloride generates a tetra-coordinated aluminum "ate" compound [C4H3N(CH2NMe2)-2-H- C4H3N(CH2NMe2)-2]Al(OSiPh3)2 (4) in 49% yield. The 1H NMR spectra of 4 at room temperature show a broad signal at δ 1.57 for NMe2 fragments and the signals for CH2N were not observed. VT 1H NMR spectra of 4 show the NMe2 fragments became two singlets (δ 1.27 and 2.12) and the CH2N exhibited two doublets (δ 2.44 and 3.56) at 240 K. The fluxional energy barrier (ΔG‡) is estimated at ca. 50 kJ/mol. The molecular structures of compounds 3 and 4 are determined by single-crystal X-ray diffractometer.

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DO - 10.1016/j.jorganchem.2007.05.013

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JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

SN - 0022-328X

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