Synthesis of 8-(dimethylamino)-1-naphthyllithium etherate: its structure in the solid (x-ray) and in solution (7Li and 1H NMR)

Johann T B H Jastrzebski; Gerard van Koten; Kees Goubitz; Cristian Arlen; Michel Pfeffer

doi:10.1016/S0022-328X(00)98740-0

Synthesis of 8-(dimethylamino)-1-naphthyllithium etherate: its structure in the solid (x-ray) and in solution (7Li and 1H NMR)

Johann T B H Jastrzebski, Gerard van Koten^*, Kees Goubitz, Cristian Arlen, Michel Pfeffer

^*Corresponding author for this work

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

Abstract

The reaction of Bu₄Li₄ with 4 molar equivalents of 1-(dimethylamino)naphthalene in diethyl ether affords novel 8-(dimethylamino)-1-naphthyllithium. Its molecular structure (X-ray) consists of two 8-(dimethylamino)-1-naphthyl groups each 3 center-2 electron bonded via C(1) to two lithium atoms and via the nitrogen lone pair to one of these lithium atoms. Diethyl ether coordination completes the pseudo tetrahedral lithium coordination sphere. Variable temperature ⁷Li and ¹H NMR spectroscopy reveals an equilibrium between the [8-Me₂NC₁₀H₆Li·OEt₂]₂ species and the ether-free [8-Me₂NC₁₀H₆Li]_n. A tetranuclear structure is proposed for the latter species.

Original language	English
Journal	Journal of Organometallic Chemistry
Volume	246
Issue number	3
DOIs	https://doi.org/10.1016/S0022-328X(00)98740-0
Publication status	Published - 26 Apr 1983
Externally published	Yes

Access to Document

10.1016/S0022-328X(00)98740-0

Cite this

@article{ea98fa179af9412bbbca454e82d69dbd,

title = "Synthesis of 8-(dimethylamino)-1-naphthyllithium etherate: its structure in the solid (x-ray) and in solution (7Li and 1H NMR)",

abstract = "The reaction of Bu4Li4 with 4 molar equivalents of 1-(dimethylamino)naphthalene in diethyl ether affords novel 8-(dimethylamino)-1-naphthyllithium. Its molecular structure (X-ray) consists of two 8-(dimethylamino)-1-naphthyl groups each 3 center-2 electron bonded via C(1) to two lithium atoms and via the nitrogen lone pair to one of these lithium atoms. Diethyl ether coordination completes the pseudo tetrahedral lithium coordination sphere. Variable temperature 7Li and 1H NMR spectroscopy reveals an equilibrium between the [8-Me2NC10H6Li·OEt2]2 species and the ether-free [8-Me2NC10H6Li]n. A tetranuclear structure is proposed for the latter species.",

author = "Jastrzebski, {Johann T B H} and {van Koten}, Gerard and Kees Goubitz and Cristian Arlen and Michel Pfeffer",

year = "1983",

month = apr,

day = "26",

doi = "10.1016/S0022-328X(00)98740-0",

language = "English",

volume = "246",

journal = "Journal of Organometallic Chemistry",

issn = "0022-328X",

publisher = "Elsevier BV",

number = "3",

}

TY - JOUR

T1 - Synthesis of 8-(dimethylamino)-1-naphthyllithium etherate

T2 - its structure in the solid (x-ray) and in solution (7Li and 1H NMR)

AU - Jastrzebski, Johann T B H

AU - van Koten, Gerard

AU - Goubitz, Kees

AU - Arlen, Cristian

AU - Pfeffer, Michel

PY - 1983/4/26

Y1 - 1983/4/26

N2 - The reaction of Bu4Li4 with 4 molar equivalents of 1-(dimethylamino)naphthalene in diethyl ether affords novel 8-(dimethylamino)-1-naphthyllithium. Its molecular structure (X-ray) consists of two 8-(dimethylamino)-1-naphthyl groups each 3 center-2 electron bonded via C(1) to two lithium atoms and via the nitrogen lone pair to one of these lithium atoms. Diethyl ether coordination completes the pseudo tetrahedral lithium coordination sphere. Variable temperature 7Li and 1H NMR spectroscopy reveals an equilibrium between the [8-Me2NC10H6Li·OEt2]2 species and the ether-free [8-Me2NC10H6Li]n. A tetranuclear structure is proposed for the latter species.

AB - The reaction of Bu4Li4 with 4 molar equivalents of 1-(dimethylamino)naphthalene in diethyl ether affords novel 8-(dimethylamino)-1-naphthyllithium. Its molecular structure (X-ray) consists of two 8-(dimethylamino)-1-naphthyl groups each 3 center-2 electron bonded via C(1) to two lithium atoms and via the nitrogen lone pair to one of these lithium atoms. Diethyl ether coordination completes the pseudo tetrahedral lithium coordination sphere. Variable temperature 7Li and 1H NMR spectroscopy reveals an equilibrium between the [8-Me2NC10H6Li·OEt2]2 species and the ether-free [8-Me2NC10H6Li]n. A tetranuclear structure is proposed for the latter species.

UR - http://www.scopus.com/inward/record.url?scp=0002124149&partnerID=8YFLogxK

U2 - 10.1016/S0022-328X(00)98740-0

DO - 10.1016/S0022-328X(00)98740-0

M3 - Article

AN - SCOPUS:0002124149

SN - 0022-328X

VL - 246

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

IS - 3

ER -

Synthesis of 8-(dimethylamino)-1-naphthyllithium etherate: its structure in the solid (x-ray) and in solution (7Li and 1H NMR)

Abstract

Access to Document

Other files and links

Fingerprint

Cite this