Synthesis and structural aspects of gallium compounds containing tridentate pincer type pyrrolyl ligands: Intramolecular hydrogen bonding of gallium aryloxides

Yu Tang Wang, Yi Chien Lin, Shu Ya Hsu, Ren Yung Chen, Pei Hsin Liu, Amitabha Datta, Chia Her Lin, Jui-Hsien Huang

Research output: Contribution to journalArticle

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Abstract

A series of gallium derivatives incorporating with pincer type tridentate symmetric and asymmetric pyrrolyl ligands are conveniently synthesized. Compilation of a symmetrical tridentate pyrrole ligand, [C4H 2NH-(2,5-CH2NHtBu)2] (1) with one equiv of n-BuLi in heptane generates lithiated 1 that turns to Ga[C 4H2N-(2,5-CH2NHtBu) 2]Cl2 (2) subjecting the addition of GaCl 3/ether suspension into diethyl ether. Reacting 2 with two equiv of lithium reagents (LiR) in same solvent originates a series of gallium compounds Ga[C4H2N-(2,5-CH2NHtBu) 2]R2 (3, R = Me; 4, R = O-C6H4-4-Me; 5, R = O-C6H3-2,6-Me2) in moderate yield through metathesis reactions. Furthermore, the combination of a tridentate asymmetrical pyrrole ligand, [C4H2NH(2-CH 2NHtBu)(5-CH2NMe2)] and n-BuLi initiates the lithiated 6 that undergoes the formation of a penta-coordinated gallium compound GaCl2[C4H2N(2-CH 2NHtBu)(5-CH2NMe2)] (7) while reacting with GaCl3. Furthermore, reacting 7 with two equivs of MeLi affords the gallium-alkyl compound, GaMe2[C4H 2N(2-CH2NHtBu)(5-CH2NMe 2)] (8) in high yield. The Ga-derivatives are characterized by 1H and 13C NMR spectroscopy and the molecular structures of 2, 3, 4, 5 and 7 are determined by single crystal X-ray diffractometry in solid state.

Original languageEnglish
Pages (from-to)12-17
Number of pages6
JournalJournal of Organometallic Chemistry
Volume745-746
DOIs
Publication statusPublished - 2013 Aug 8

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Gallium compounds
gallium compounds
Gallium
Hydrogen Bonding
gallium
Hydrogen bonds
Pyrroles
Ligands
pyrroles
Ether
ligands
Ethers
hydrogen
synthesis
alkyl compounds
methylidyne
Derivatives
Heptanes
diethyl ether
metathesis

All Science Journal Classification (ASJC) codes

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

Cite this

Wang, Yu Tang ; Lin, Yi Chien ; Hsu, Shu Ya ; Chen, Ren Yung ; Liu, Pei Hsin ; Datta, Amitabha ; Lin, Chia Her ; Huang, Jui-Hsien. / Synthesis and structural aspects of gallium compounds containing tridentate pincer type pyrrolyl ligands : Intramolecular hydrogen bonding of gallium aryloxides. In: Journal of Organometallic Chemistry. 2013 ; Vol. 745-746. pp. 12-17.
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title = "Synthesis and structural aspects of gallium compounds containing tridentate pincer type pyrrolyl ligands: Intramolecular hydrogen bonding of gallium aryloxides",
abstract = "A series of gallium derivatives incorporating with pincer type tridentate symmetric and asymmetric pyrrolyl ligands are conveniently synthesized. Compilation of a symmetrical tridentate pyrrole ligand, [C4H 2NH-(2,5-CH2NHtBu)2] (1) with one equiv of n-BuLi in heptane generates lithiated 1 that turns to Ga[C 4H2N-(2,5-CH2NHtBu) 2]Cl2 (2) subjecting the addition of GaCl 3/ether suspension into diethyl ether. Reacting 2 with two equiv of lithium reagents (LiR) in same solvent originates a series of gallium compounds Ga[C4H2N-(2,5-CH2NHtBu) 2]R2 (3, R = Me; 4, R = O-C6H4-4-Me; 5, R = O-C6H3-2,6-Me2) in moderate yield through metathesis reactions. Furthermore, the combination of a tridentate asymmetrical pyrrole ligand, [C4H2NH(2-CH 2NHtBu)(5-CH2NMe2)] and n-BuLi initiates the lithiated 6 that undergoes the formation of a penta-coordinated gallium compound GaCl2[C4H2N(2-CH 2NHtBu)(5-CH2NMe2)] (7) while reacting with GaCl3. Furthermore, reacting 7 with two equivs of MeLi affords the gallium-alkyl compound, GaMe2[C4H 2N(2-CH2NHtBu)(5-CH2NMe 2)] (8) in high yield. The Ga-derivatives are characterized by 1H and 13C NMR spectroscopy and the molecular structures of 2, 3, 4, 5 and 7 are determined by single crystal X-ray diffractometry in solid state.",
author = "Wang, {Yu Tang} and Lin, {Yi Chien} and Hsu, {Shu Ya} and Chen, {Ren Yung} and Liu, {Pei Hsin} and Amitabha Datta and Lin, {Chia Her} and Jui-Hsien Huang",
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Synthesis and structural aspects of gallium compounds containing tridentate pincer type pyrrolyl ligands : Intramolecular hydrogen bonding of gallium aryloxides. / Wang, Yu Tang; Lin, Yi Chien; Hsu, Shu Ya; Chen, Ren Yung; Liu, Pei Hsin; Datta, Amitabha; Lin, Chia Her; Huang, Jui-Hsien.

In: Journal of Organometallic Chemistry, Vol. 745-746, 08.08.2013, p. 12-17.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis and structural aspects of gallium compounds containing tridentate pincer type pyrrolyl ligands

T2 - Intramolecular hydrogen bonding of gallium aryloxides

AU - Wang, Yu Tang

AU - Lin, Yi Chien

AU - Hsu, Shu Ya

AU - Chen, Ren Yung

AU - Liu, Pei Hsin

AU - Datta, Amitabha

AU - Lin, Chia Her

AU - Huang, Jui-Hsien

PY - 2013/8/8

Y1 - 2013/8/8

N2 - A series of gallium derivatives incorporating with pincer type tridentate symmetric and asymmetric pyrrolyl ligands are conveniently synthesized. Compilation of a symmetrical tridentate pyrrole ligand, [C4H 2NH-(2,5-CH2NHtBu)2] (1) with one equiv of n-BuLi in heptane generates lithiated 1 that turns to Ga[C 4H2N-(2,5-CH2NHtBu) 2]Cl2 (2) subjecting the addition of GaCl 3/ether suspension into diethyl ether. Reacting 2 with two equiv of lithium reagents (LiR) in same solvent originates a series of gallium compounds Ga[C4H2N-(2,5-CH2NHtBu) 2]R2 (3, R = Me; 4, R = O-C6H4-4-Me; 5, R = O-C6H3-2,6-Me2) in moderate yield through metathesis reactions. Furthermore, the combination of a tridentate asymmetrical pyrrole ligand, [C4H2NH(2-CH 2NHtBu)(5-CH2NMe2)] and n-BuLi initiates the lithiated 6 that undergoes the formation of a penta-coordinated gallium compound GaCl2[C4H2N(2-CH 2NHtBu)(5-CH2NMe2)] (7) while reacting with GaCl3. Furthermore, reacting 7 with two equivs of MeLi affords the gallium-alkyl compound, GaMe2[C4H 2N(2-CH2NHtBu)(5-CH2NMe 2)] (8) in high yield. The Ga-derivatives are characterized by 1H and 13C NMR spectroscopy and the molecular structures of 2, 3, 4, 5 and 7 are determined by single crystal X-ray diffractometry in solid state.

AB - A series of gallium derivatives incorporating with pincer type tridentate symmetric and asymmetric pyrrolyl ligands are conveniently synthesized. Compilation of a symmetrical tridentate pyrrole ligand, [C4H 2NH-(2,5-CH2NHtBu)2] (1) with one equiv of n-BuLi in heptane generates lithiated 1 that turns to Ga[C 4H2N-(2,5-CH2NHtBu) 2]Cl2 (2) subjecting the addition of GaCl 3/ether suspension into diethyl ether. Reacting 2 with two equiv of lithium reagents (LiR) in same solvent originates a series of gallium compounds Ga[C4H2N-(2,5-CH2NHtBu) 2]R2 (3, R = Me; 4, R = O-C6H4-4-Me; 5, R = O-C6H3-2,6-Me2) in moderate yield through metathesis reactions. Furthermore, the combination of a tridentate asymmetrical pyrrole ligand, [C4H2NH(2-CH 2NHtBu)(5-CH2NMe2)] and n-BuLi initiates the lithiated 6 that undergoes the formation of a penta-coordinated gallium compound GaCl2[C4H2N(2-CH 2NHtBu)(5-CH2NMe2)] (7) while reacting with GaCl3. Furthermore, reacting 7 with two equivs of MeLi affords the gallium-alkyl compound, GaMe2[C4H 2N(2-CH2NHtBu)(5-CH2NMe 2)] (8) in high yield. The Ga-derivatives are characterized by 1H and 13C NMR spectroscopy and the molecular structures of 2, 3, 4, 5 and 7 are determined by single crystal X-ray diffractometry in solid state.

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U2 - 10.1016/j.jorganchem.2013.07.012

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