Electronic communication through the ureylene bridge: Spectroscopy, structure and electrochemistry of dimethyl 1′,1′-ureylenedi (1-ferrocenecarboxylate)

Khaled Mahmoud; Yi Tao Long; Gabriele Schatte; Heinz Bernhard Kraatz

doi:10.1016/j.jorganchem.2004.04.016

Electronic communication through the ureylene bridge: Spectroscopy, structure and electrochemistry of dimethyl 1′,1′-ureylenedi (1-ferrocenecarboxylate)

Khaled Mahmoud
, Yi Tao Long
, Gabriele Schatte
, Heinz Bernhard Kraatz^*

^*Corresponding author for this work

University of Saskatchewan

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

26 Citations (Scopus)

Abstract

Dimethyl 1′,1′-ureylenedi (1-ferrocenecarboxylate) (1) formed during the synthesis of 1-amino, 1′-ferrocenecarboxylic acid shows virtual molecular centrosymmetry. Electronic coupling between the two Fc groups through the ureylene bridge results in both Fc groups being individually oxidizable (ΔE_1/2≫0.14 V). The possible existence of intermolecular electronic communication has discussed. The oxidation was followed by spectroelectrochemistry. The separation between the two halfwave potentials ΔE_1/2 =137±5 mV and the comproportionation constant K_c=207.

Original language	English
Pages (from-to)	2250-2255
Number of pages	6
Journal	Journal of Organometallic Chemistry
Volume	689
Issue number	13
DOIs	https://doi.org/10.1016/j.jorganchem.2004.04.016
Publication status	Published - 1 Jul 2004
Externally published	Yes

Keywords

Diferrocene
Electronic communication
Spectroelectrochemistry
Ureylene bridge

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10.1016/j.jorganchem.2004.04.016

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title = "Electronic communication through the ureylene bridge: Spectroscopy, structure and electrochemistry of dimethyl 1′,1′-ureylenedi (1-ferrocenecarboxylate)",

abstract = "Dimethyl 1′,1′-ureylenedi (1-ferrocenecarboxylate) (1) formed during the synthesis of 1-amino, 1′-ferrocenecarboxylic acid shows virtual molecular centrosymmetry. Electronic coupling between the two Fc groups through the ureylene bridge results in both Fc groups being individually oxidizable (ΔE1/2≫0.14 V). The possible existence of intermolecular electronic communication has discussed. The oxidation was followed by spectroelectrochemistry. The separation between the two halfwave potentials ΔE1/2 =137±5 mV and the comproportionation constant Kc=207.",

keywords = "Diferrocene, Electronic communication, Spectroelectrochemistry, Ureylene bridge",

author = "Khaled Mahmoud and Long, \{Yi Tao\} and Gabriele Schatte and Kraatz, \{Heinz Bernhard\}",

year = "2004",

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doi = "10.1016/j.jorganchem.2004.04.016",

language = "English",

volume = "689",

pages = "2250--2255",

journal = "Journal of Organometallic Chemistry",

issn = "0022-328X",

publisher = "Elsevier B.V.",

number = "13",

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TY - JOUR

T1 - Electronic communication through the ureylene bridge

T2 - Spectroscopy, structure and electrochemistry of dimethyl 1′,1′-ureylenedi (1-ferrocenecarboxylate)

AU - Mahmoud, Khaled

AU - Long, Yi Tao

AU - Schatte, Gabriele

AU - Kraatz, Heinz Bernhard

PY - 2004/7/1

Y1 - 2004/7/1

N2 - Dimethyl 1′,1′-ureylenedi (1-ferrocenecarboxylate) (1) formed during the synthesis of 1-amino, 1′-ferrocenecarboxylic acid shows virtual molecular centrosymmetry. Electronic coupling between the two Fc groups through the ureylene bridge results in both Fc groups being individually oxidizable (ΔE1/2≫0.14 V). The possible existence of intermolecular electronic communication has discussed. The oxidation was followed by spectroelectrochemistry. The separation between the two halfwave potentials ΔE1/2 =137±5 mV and the comproportionation constant Kc=207.

AB - Dimethyl 1′,1′-ureylenedi (1-ferrocenecarboxylate) (1) formed during the synthesis of 1-amino, 1′-ferrocenecarboxylic acid shows virtual molecular centrosymmetry. Electronic coupling between the two Fc groups through the ureylene bridge results in both Fc groups being individually oxidizable (ΔE1/2≫0.14 V). The possible existence of intermolecular electronic communication has discussed. The oxidation was followed by spectroelectrochemistry. The separation between the two halfwave potentials ΔE1/2 =137±5 mV and the comproportionation constant Kc=207.

KW - Diferrocene

KW - Electronic communication

KW - Spectroelectrochemistry

KW - Ureylene bridge

UR - https://www.scopus.com/pages/publications/2542436068

U2 - 10.1016/j.jorganchem.2004.04.016

DO - 10.1016/j.jorganchem.2004.04.016

M3 - Article

AN - SCOPUS:2542436068

SN - 0022-328X

VL - 689

SP - 2250

EP - 2255

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

IS - 13

ER -

Electronic communication through the ureylene bridge: Spectroscopy, structure and electrochemistry of dimethyl 1′,1′-ureylenedi (1-ferrocenecarboxylate)

Abstract

Keywords

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