Towards the formation of dimeric and trimeric lithium benzamidinates: Characterization of intermediate structures

A. Lisovskii; M. Botoshansky; M. S. Eisen

doi:10.1039/b100251l

Towards the formation of dimeric and trimeric lithium benzamidinates: Characterization of intermediate structures

A. Lisovskii, M. Botoshansky, M. S. Eisen^*

^*Corresponding author for this work

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

31 Scopus citations

Abstract

p-Toluonitrile reacts with LiN(TMS)₂ in diethyl ether (1 : 1) to yield a dimeric complex 1 containing a lithium benzamidinate unit, a molecule of p-toluonitrile attached to the lithium atom and a molecule of lithium bis(trimethylsilyl)amide coordinated to a lithium-nitrogen bond, of the benzamidinate unit, forming a four-membered ring. The crystal structure of 1 shows the molecularity, the stereochemistry and the manner of activation of nitriles by lithium amido salts in the formation of amidinates. When the same reaction is carried out in hexane, the trimeric complex 2 is formed, containing lithium atoms simultaneously π- and σ-bonded to amidine moieties. When the ratio of p-toluonitrile and LiN(TMS)₂ in diethyl ether-hexane is 2 : 1, complex 1 is obtained, which can be treated with two equivalents of LiN(TMS)₂ to produce 3.

Original language	English
Pages (from-to)	1692-1698
Number of pages	7
Journal	Journal of the Chemical Society. Dalton Transactions
Issue number	11
DOIs	https://doi.org/10.1039/b100251l
State	Published - 2001
Externally published	Yes

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title = "Towards the formation of dimeric and trimeric lithium benzamidinates: Characterization of intermediate structures",

abstract = "p-Toluonitrile reacts with LiN(TMS)2 in diethyl ether (1 : 1) to yield a dimeric complex 1 containing a lithium benzamidinate unit, a molecule of p-toluonitrile attached to the lithium atom and a molecule of lithium bis(trimethylsilyl)amide coordinated to a lithium-nitrogen bond, of the benzamidinate unit, forming a four-membered ring. The crystal structure of 1 shows the molecularity, the stereochemistry and the manner of activation of nitriles by lithium amido salts in the formation of amidinates. When the same reaction is carried out in hexane, the trimeric complex 2 is formed, containing lithium atoms simultaneously π- and σ-bonded to amidine moieties. When the ratio of p-toluonitrile and LiN(TMS)2 in diethyl ether-hexane is 2 : 1, complex 1 is obtained, which can be treated with two equivalents of LiN(TMS)2 to produce 3.",

author = "A. Lisovskii and M. Botoshansky and Eisen, {M. S.}",

year = "2001",

doi = "10.1039/b100251l",

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publisher = "Royal Society of Chemistry",

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TY - JOUR

T1 - Towards the formation of dimeric and trimeric lithium benzamidinates

T2 - Characterization of intermediate structures

AU - Lisovskii, A.

AU - Botoshansky, M.

AU - Eisen, M. S.

PY - 2001

Y1 - 2001

N2 - p-Toluonitrile reacts with LiN(TMS)2 in diethyl ether (1 : 1) to yield a dimeric complex 1 containing a lithium benzamidinate unit, a molecule of p-toluonitrile attached to the lithium atom and a molecule of lithium bis(trimethylsilyl)amide coordinated to a lithium-nitrogen bond, of the benzamidinate unit, forming a four-membered ring. The crystal structure of 1 shows the molecularity, the stereochemistry and the manner of activation of nitriles by lithium amido salts in the formation of amidinates. When the same reaction is carried out in hexane, the trimeric complex 2 is formed, containing lithium atoms simultaneously π- and σ-bonded to amidine moieties. When the ratio of p-toluonitrile and LiN(TMS)2 in diethyl ether-hexane is 2 : 1, complex 1 is obtained, which can be treated with two equivalents of LiN(TMS)2 to produce 3.

AB - p-Toluonitrile reacts with LiN(TMS)2 in diethyl ether (1 : 1) to yield a dimeric complex 1 containing a lithium benzamidinate unit, a molecule of p-toluonitrile attached to the lithium atom and a molecule of lithium bis(trimethylsilyl)amide coordinated to a lithium-nitrogen bond, of the benzamidinate unit, forming a four-membered ring. The crystal structure of 1 shows the molecularity, the stereochemistry and the manner of activation of nitriles by lithium amido salts in the formation of amidinates. When the same reaction is carried out in hexane, the trimeric complex 2 is formed, containing lithium atoms simultaneously π- and σ-bonded to amidine moieties. When the ratio of p-toluonitrile and LiN(TMS)2 in diethyl ether-hexane is 2 : 1, complex 1 is obtained, which can be treated with two equivalents of LiN(TMS)2 to produce 3.

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DO - 10.1039/b100251l

M3 - 文章

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SN - 1470-479X

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JO - Journal of the Chemical Society. Dalton Transactions

JF - Journal of the Chemical Society. Dalton Transactions

IS - 11

ER -

Towards the formation of dimeric and trimeric lithium benzamidinates: Characterization of intermediate structures

Abstract

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