Difunctionalization of primary aromatic amines with ethylene; synthesis of μ-arylnitrilobis(ethane-2,1-diyl)dimercury(II) complexes. Crystal structure of 2,4,6-Me3C6H2N-(CH2CH2HgCl)2

G. B. Deacon, B. M. Gatehouse, L. W. Guddat, S. C. Ney

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Abstract

Reaction of primary aromatic amines, mercuric acetate, and ethylene in tetrahydrofuran under pressure (ca. 40 atm) yields the organomercurials ArN(CH2CH2-HgOAc)2 (Ar = Ph, 2-ClC6H4, 3-ClC6H4, or 4-ClC6H4) or, after treatment of the crude products with sodium halide, ArN(CH2CH2HgX)2 (Ar = 4-MeC6H4, 4-MeOC6H4, or 2,4,6-Me3C6H2, X = Cl; Ar = 2,4-Cl2C6H3, 2,6-Cl2C6H3, or 2,4,6-Br3C6H2, X = Br). The X-ray diffraction study of 2,4,6-Me3C6H2N(CH2CH2HgCl)2 shows the molecules to have near linear C-Hg-Cl stereochemistry, and to be arranged in centrosymmetric dimers with weak Hg ··· Cl intermolecular bonding.

Original languageEnglish
Pages (from-to)1-4
Number of pages1
JournalJournal of Organometallic Chemistry
Volume375
Issue number1
DOIs
Publication statusPublished - 3 Oct 1989

Cite this

@article{ce2bf3fb63df4ca0b8d949006c06c2e2,
title = "Difunctionalization of primary aromatic amines with ethylene; synthesis of μ-arylnitrilobis(ethane-2,1-diyl)dimercury(II) complexes. Crystal structure of 2,4,6-Me3C6H2N-(CH2CH2HgCl)2",
abstract = "Reaction of primary aromatic amines, mercuric acetate, and ethylene in tetrahydrofuran under pressure (ca. 40 atm) yields the organomercurials ArN(CH2CH2-HgOAc)2 (Ar = Ph, 2-ClC6H4, 3-ClC6H4, or 4-ClC6H4) or, after treatment of the crude products with sodium halide, ArN(CH2CH2HgX)2 (Ar = 4-MeC6H4, 4-MeOC6H4, or 2,4,6-Me3C6H2, X = Cl; Ar = 2,4-Cl2C6H3, 2,6-Cl2C6H3, or 2,4,6-Br3C6H2, X = Br). The X-ray diffraction study of 2,4,6-Me3C6H2N(CH2CH2HgCl)2 shows the molecules to have near linear C-Hg-Cl stereochemistry, and to be arranged in centrosymmetric dimers with weak Hg ··· Cl intermolecular bonding.",
author = "Deacon, {G. B.} and Gatehouse, {B. M.} and Guddat, {L. W.} and Ney, {S. C.}",
year = "1989",
month = "10",
day = "3",
doi = "10.1016/0022-328X(89)85095-8",
language = "English",
volume = "375",
pages = "1--4",
journal = "Journal of Organometallic Chemistry",
issn = "0022-328X",
publisher = "Elsevier",
number = "1",

}

Difunctionalization of primary aromatic amines with ethylene; synthesis of μ-arylnitrilobis(ethane-2,1-diyl)dimercury(II) complexes. Crystal structure of 2,4,6-Me3C6H2N-(CH2CH2HgCl)2. / Deacon, G. B.; Gatehouse, B. M.; Guddat, L. W.; Ney, S. C.

In: Journal of Organometallic Chemistry, Vol. 375, No. 1, 03.10.1989, p. 1-4.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - Difunctionalization of primary aromatic amines with ethylene; synthesis of μ-arylnitrilobis(ethane-2,1-diyl)dimercury(II) complexes. Crystal structure of 2,4,6-Me3C6H2N-(CH2CH2HgCl)2

AU - Deacon, G. B.

AU - Gatehouse, B. M.

AU - Guddat, L. W.

AU - Ney, S. C.

PY - 1989/10/3

Y1 - 1989/10/3

N2 - Reaction of primary aromatic amines, mercuric acetate, and ethylene in tetrahydrofuran under pressure (ca. 40 atm) yields the organomercurials ArN(CH2CH2-HgOAc)2 (Ar = Ph, 2-ClC6H4, 3-ClC6H4, or 4-ClC6H4) or, after treatment of the crude products with sodium halide, ArN(CH2CH2HgX)2 (Ar = 4-MeC6H4, 4-MeOC6H4, or 2,4,6-Me3C6H2, X = Cl; Ar = 2,4-Cl2C6H3, 2,6-Cl2C6H3, or 2,4,6-Br3C6H2, X = Br). The X-ray diffraction study of 2,4,6-Me3C6H2N(CH2CH2HgCl)2 shows the molecules to have near linear C-Hg-Cl stereochemistry, and to be arranged in centrosymmetric dimers with weak Hg ··· Cl intermolecular bonding.

AB - Reaction of primary aromatic amines, mercuric acetate, and ethylene in tetrahydrofuran under pressure (ca. 40 atm) yields the organomercurials ArN(CH2CH2-HgOAc)2 (Ar = Ph, 2-ClC6H4, 3-ClC6H4, or 4-ClC6H4) or, after treatment of the crude products with sodium halide, ArN(CH2CH2HgX)2 (Ar = 4-MeC6H4, 4-MeOC6H4, or 2,4,6-Me3C6H2, X = Cl; Ar = 2,4-Cl2C6H3, 2,6-Cl2C6H3, or 2,4,6-Br3C6H2, X = Br). The X-ray diffraction study of 2,4,6-Me3C6H2N(CH2CH2HgCl)2 shows the molecules to have near linear C-Hg-Cl stereochemistry, and to be arranged in centrosymmetric dimers with weak Hg ··· Cl intermolecular bonding.

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U2 - 10.1016/0022-328X(89)85095-8

DO - 10.1016/0022-328X(89)85095-8

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