Bifunctional chelates with aliphatic amine donors for labeling of biomolecules with the {Tc(CO)3}+ and {Re(CO) 3}+ cores: The crystal and molecular structure of [Re(CO)3{(H2NCH2CH2)2 N(CH2)4CO2Me}]Br

Sangeeta Ray Banerjee; John W. Babich; Jon Zubieta

doi:10.1016/j.inoche.2004.01.008

Bifunctional chelates with aliphatic amine donors for labeling of biomolecules with the {Tc(CO)₃}⁺ and {Re(CO) ₃}⁺ cores: The crystal and molecular structure of [Re(CO)₃{(H₂NCH₂CH₂)₂ N(CH₂)₄CO₂Me}]Br

Sangeeta Ray Banerjee, John W. Babich, Jon Zubieta

Department of Chemistry

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

23 Scopus citations

Abstract

A general synthetic approach to the design of bis(ethylamine) derivatives of single amino acid chelates has been developed. In general, protection of diethylenetriamine as the phthalimide, followed by reaction with the appropriate bromoalkylcarboxylate and deprotection, yields the bifunctional reagents (H₂NCH₂CH₂)₂N-R-CO ₂H. Reaction of the bis(aminoethyl)aminovaleric acid derivative with (NEt₄)₂[Re(CO)₃Br₃] in methanol yields [Re(CO)₃{(H₂NCH₂CH₂) ₂N(CH₂)₄CO₂Me}]Br (1Br), the first example of the {Re(CO)₃}⁺ core ligated to exclusively aliphatic amine donors. Crystal data: C₁₃H₂₃BrN ₃O₅Re (1Br), monoclinic P2₁/c, a=8.3419(5) Å, b=9.4018(6) Å, c=23.569(1) Å, β=99.165(1)°, V=1824.9(2) Å³, Z=4, D_calc=2.065 g cm^-3.

Original language	English (US)
Pages (from-to)	481-484
Number of pages	4
Journal	Inorganic Chemistry Communications
Volume	7
Issue number	4
DOIs	https://doi.org/10.1016/j.inoche.2004.01.008
State	Published - Apr 2004

Keywords

Bifunctional chelates
Single amino acid chelates
{M(CO)} core

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Inorganic Chemistry
Materials Chemistry

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10.1016/j.inoche.2004.01.008

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Bifunctional chelates with aliphatic amine donors for labeling of biomolecules with the {Tc(CO)₃}⁺ and {Re(CO) ₃}⁺ cores: The crystal and molecular structure of [Re(CO)₃{(H₂NCH₂CH₂)₂ N(CH₂)₄CO₂Me}]Br. / Banerjee, Sangeeta Ray; Babich, John W.; Zubieta, Jon.
In: Inorganic Chemistry Communications, Vol. 7, No. 4, 04.2004, p. 481-484.

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

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title = "Bifunctional chelates with aliphatic amine donors for labeling of biomolecules with the {Tc(CO)3}+ and {Re(CO) 3}+ cores: The crystal and molecular structure of [Re(CO)3{(H2NCH2CH2)2 N(CH2)4CO2Me}]Br",

abstract = "A general synthetic approach to the design of bis(ethylamine) derivatives of single amino acid chelates has been developed. In general, protection of diethylenetriamine as the phthalimide, followed by reaction with the appropriate bromoalkylcarboxylate and deprotection, yields the bifunctional reagents (H2NCH2CH2)2N-R-CO 2H. Reaction of the bis(aminoethyl)aminovaleric acid derivative with (NEt4)2[Re(CO)3Br3] in methanol yields [Re(CO)3{(H2NCH2CH2) 2N(CH2)4CO2Me}]Br (1Br), the first example of the {Re(CO)3}+ core ligated to exclusively aliphatic amine donors. Crystal data: C13H23BrN 3O5Re (1Br), monoclinic P21/c, a=8.3419(5) {\AA}, b=9.4018(6) {\AA}, c=23.569(1) {\AA}, β=99.165(1)°, V=1824.9(2) {\AA}3, Z=4, Dcalc=2.065 g cm-3.",

keywords = "Bifunctional chelates, Single amino acid chelates, {M(CO)} core",

author = "Banerjee, {Sangeeta Ray} and Babich, {John W.} and Jon Zubieta",

note = "Funding Information: This work was supported by a grant from the Department of Energy (DOE), Office of Health and Environmental Research D2-FG02-99ER62791",

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T1 - Bifunctional chelates with aliphatic amine donors for labeling of biomolecules with the {Tc(CO)3}+ and {Re(CO) 3}+ cores

T2 - The crystal and molecular structure of [Re(CO)3{(H2NCH2CH2)2 N(CH2)4CO2Me}]Br

AU - Banerjee, Sangeeta Ray

AU - Babich, John W.

AU - Zubieta, Jon

N1 - Funding Information: This work was supported by a grant from the Department of Energy (DOE), Office of Health and Environmental Research D2-FG02-99ER62791

PY - 2004/4

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N2 - A general synthetic approach to the design of bis(ethylamine) derivatives of single amino acid chelates has been developed. In general, protection of diethylenetriamine as the phthalimide, followed by reaction with the appropriate bromoalkylcarboxylate and deprotection, yields the bifunctional reagents (H2NCH2CH2)2N-R-CO 2H. Reaction of the bis(aminoethyl)aminovaleric acid derivative with (NEt4)2[Re(CO)3Br3] in methanol yields [Re(CO)3{(H2NCH2CH2) 2N(CH2)4CO2Me}]Br (1Br), the first example of the {Re(CO)3}+ core ligated to exclusively aliphatic amine donors. Crystal data: C13H23BrN 3O5Re (1Br), monoclinic P21/c, a=8.3419(5) Å, b=9.4018(6) Å, c=23.569(1) Å, β=99.165(1)°, V=1824.9(2) Å3, Z=4, Dcalc=2.065 g cm-3.

AB - A general synthetic approach to the design of bis(ethylamine) derivatives of single amino acid chelates has been developed. In general, protection of diethylenetriamine as the phthalimide, followed by reaction with the appropriate bromoalkylcarboxylate and deprotection, yields the bifunctional reagents (H2NCH2CH2)2N-R-CO 2H. Reaction of the bis(aminoethyl)aminovaleric acid derivative with (NEt4)2[Re(CO)3Br3] in methanol yields [Re(CO)3{(H2NCH2CH2) 2N(CH2)4CO2Me}]Br (1Br), the first example of the {Re(CO)3}+ core ligated to exclusively aliphatic amine donors. Crystal data: C13H23BrN 3O5Re (1Br), monoclinic P21/c, a=8.3419(5) Å, b=9.4018(6) Å, c=23.569(1) Å, β=99.165(1)°, V=1824.9(2) Å3, Z=4, Dcalc=2.065 g cm-3.

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