Hexameric chiral α-amino lithium alkoxides: A solid-state and theoretical structural investigation

David R. Armstrong; Robert P. Davies; Paul R. Raithby; Ronald Snaith; Andrew E.H. Wheatley

doi:10.1039/a809942a

Hexameric chiral α-amino lithium alkoxides: A solid-state and theoretical structural investigation

David R. Armstrong, Robert P. Davies, Paul R. Raithby, Ronald Snaith, Andrew E.H. Wheatley

Research output: Contribution to journal › Article

22 Citations (Scopus)

Abstract

The nucleophilic reagents lithium N-methylpiperazide, 1-Li, and lithium N,N,N'-trimethylethylenediamide, 2-Li, react with 1 equiv. of 4- methoxybenzaldehyde and 2-methylbenzaldehyde respectively to afford the corresponding chiral α-amino lithium alkoxides, (3)₆ · 2PhMe · THF and (4)₆ · 2PhMe, which are hexamers in the solid state. Stabilisation of the metal centres is assisted by dative coordination of the dialkylamine α-N- centres. While for (3)₆ · 2PhMe. THF this is rationalised in terms of steric constraints imposed by the employment of a heterocyclic dialkylamine, for (4)₆ · 2PhMe it contrasts starkly with previously observed structural analogues. Ab initio MO calculations are employed to investigate the relationship between structure and ligand chirality.

Original language	English
Pages (from-to)	499-507
Number of pages	9
Journal	New Journal of Chemistry
Volume	23
Issue number	5
DOIs	https://doi.org/10.1039/a809942a
Publication status	Published - 1999

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Materials Chemistry

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title = "Hexameric chiral α-amino lithium alkoxides: A solid-state and theoretical structural investigation",

abstract = "The nucleophilic reagents lithium N-methylpiperazide, 1-Li, and lithium N,N,N'-trimethylethylenediamide, 2-Li, react with 1 equiv. of 4- methoxybenzaldehyde and 2-methylbenzaldehyde respectively to afford the corresponding chiral α-amino lithium alkoxides, (3)6 · 2PhMe · THF and (4)6 · 2PhMe, which are hexamers in the solid state. Stabilisation of the metal centres is assisted by dative coordination of the dialkylamine α-N- centres. While for (3)6 · 2PhMe. THF this is rationalised in terms of steric constraints imposed by the employment of a heterocyclic dialkylamine, for (4)6 · 2PhMe it contrasts starkly with previously observed structural analogues. Ab initio MO calculations are employed to investigate the relationship between structure and ligand chirality.",

author = "Armstrong, {David R.} and Davies, {Robert P.} and Raithby, {Paul R.} and Ronald Snaith and Wheatley, {Andrew E.H.}",

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publisher = "Royal Society of Chemistry",

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T1 - Hexameric chiral α-amino lithium alkoxides

T2 - A solid-state and theoretical structural investigation

AU - Armstrong, David R.

AU - Davies, Robert P.

AU - Raithby, Paul R.

AU - Snaith, Ronald

AU - Wheatley, Andrew E.H.

PY - 1999

Y1 - 1999

N2 - The nucleophilic reagents lithium N-methylpiperazide, 1-Li, and lithium N,N,N'-trimethylethylenediamide, 2-Li, react with 1 equiv. of 4- methoxybenzaldehyde and 2-methylbenzaldehyde respectively to afford the corresponding chiral α-amino lithium alkoxides, (3)6 · 2PhMe · THF and (4)6 · 2PhMe, which are hexamers in the solid state. Stabilisation of the metal centres is assisted by dative coordination of the dialkylamine α-N- centres. While for (3)6 · 2PhMe. THF this is rationalised in terms of steric constraints imposed by the employment of a heterocyclic dialkylamine, for (4)6 · 2PhMe it contrasts starkly with previously observed structural analogues. Ab initio MO calculations are employed to investigate the relationship between structure and ligand chirality.

AB - The nucleophilic reagents lithium N-methylpiperazide, 1-Li, and lithium N,N,N'-trimethylethylenediamide, 2-Li, react with 1 equiv. of 4- methoxybenzaldehyde and 2-methylbenzaldehyde respectively to afford the corresponding chiral α-amino lithium alkoxides, (3)6 · 2PhMe · THF and (4)6 · 2PhMe, which are hexamers in the solid state. Stabilisation of the metal centres is assisted by dative coordination of the dialkylamine α-N- centres. While for (3)6 · 2PhMe. THF this is rationalised in terms of steric constraints imposed by the employment of a heterocyclic dialkylamine, for (4)6 · 2PhMe it contrasts starkly with previously observed structural analogues. Ab initio MO calculations are employed to investigate the relationship between structure and ligand chirality.

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