Discovery of the first metallaquinone [11]

Nissim Ashkenazi; Arkadi Vigalok; Srinivasan Parthiban; David, Yonit Ben David; Linda J. W. Shimon; Jan M. L. Martin; David Milstein

doi:10.1021/ja001759d

Discovery of the first metallaquinone [11]

Nissim Ashkenazi, Arkadi Vigalok, Srinivasan Parthiban, David, Yonit Ben David, Linda J. W. Shimon, Jan M. L. Martin^*, David Milstein^*

^*Corresponding author for this work

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

60 Citations (Scopus)

Abstract

Quinoid systems such as quinones, quinone methides, quinodimethanes, and quinodiimines have been widely investigated regarding their chemical, biological, and physical properties.1 Of special interest are their utility as charge transfer complexes due to the relatively low energy barrier between the ground and excited states. Some metal stabilized quinone methides have also been reported recently.2 Remarkably, no metallaquinone, that is, a compound in which one of the oxygen atoms of a quinone has been replaced by a metal, has hitherto been reported. Such a compound is expected to have a strong dipolar contribution to the excited state compared to its biradical nature in quinones. We know of only one example of a stable quinoid compound which contains a heavier element (phosphorus)3 instead of the oxygen.

Original language	English
Pages (from-to)	8797-8798
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	122
Issue number	36
DOIs	https://doi.org/10.1021/ja001759d
Publication status	Published - 13 Sept 2000

Funding

D.M. is the Israel Matz Professor of Organic Chemistry, and J.M., the Incumbent of the Helen and Milton A. Kimmelman Career Development Chair. This research was supported by the Minerva Foundation, Munich, Germany, by the U.S.-Israel Binational Science Foundation, Jerusalem, Israel, and by the Tashtiyot program of the Ministry of Science (Israel).

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja001759d

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title = "Discovery of the first metallaquinone [11]",

abstract = "Quinoid systems such as quinones, quinone methides, quinodimethanes, and quinodiimines have been widely investigated regarding their chemical, biological, and physical properties.1 Of special interest are their utility as charge transfer complexes due to the relatively low energy barrier between the ground and excited states. Some metal stabilized quinone methides have also been reported recently.2 Remarkably, no metallaquinone, that is, a compound in which one of the oxygen atoms of a quinone has been replaced by a metal, has hitherto been reported. Such a compound is expected to have a strong dipolar contribution to the excited state compared to its biradical nature in quinones. We know of only one example of a stable quinoid compound which contains a heavier element (phosphorus)3 instead of the oxygen.",

author = "Nissim Ashkenazi and Arkadi Vigalok and Srinivasan Parthiban and \{Ben David\}, \{David, Yonit\} and Shimon, \{Linda J. W.\} and Martin, \{Jan M. L.\} and David Milstein",

year = "2000",

month = sep,

day = "13",

doi = "10.1021/ja001759d",

language = "English",

volume = "122",

pages = "8797--8798",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "36",

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TY - JOUR

T1 - Discovery of the first metallaquinone [11]

AU - Ashkenazi, Nissim

AU - Vigalok, Arkadi

AU - Parthiban, Srinivasan

AU - Ben David, David, Yonit

AU - Shimon, Linda J. W.

AU - Martin, Jan M. L.

AU - Milstein, David

PY - 2000/9/13

Y1 - 2000/9/13

N2 - Quinoid systems such as quinones, quinone methides, quinodimethanes, and quinodiimines have been widely investigated regarding their chemical, biological, and physical properties.1 Of special interest are their utility as charge transfer complexes due to the relatively low energy barrier between the ground and excited states. Some metal stabilized quinone methides have also been reported recently.2 Remarkably, no metallaquinone, that is, a compound in which one of the oxygen atoms of a quinone has been replaced by a metal, has hitherto been reported. Such a compound is expected to have a strong dipolar contribution to the excited state compared to its biradical nature in quinones. We know of only one example of a stable quinoid compound which contains a heavier element (phosphorus)3 instead of the oxygen.

AB - Quinoid systems such as quinones, quinone methides, quinodimethanes, and quinodiimines have been widely investigated regarding their chemical, biological, and physical properties.1 Of special interest are their utility as charge transfer complexes due to the relatively low energy barrier between the ground and excited states. Some metal stabilized quinone methides have also been reported recently.2 Remarkably, no metallaquinone, that is, a compound in which one of the oxygen atoms of a quinone has been replaced by a metal, has hitherto been reported. Such a compound is expected to have a strong dipolar contribution to the excited state compared to its biradical nature in quinones. We know of only one example of a stable quinoid compound which contains a heavier element (phosphorus)3 instead of the oxygen.

UR - https://www.scopus.com/pages/publications/0034644410

U2 - 10.1021/ja001759d

DO - 10.1021/ja001759d

M3 - Letter

SN - 0002-7863

VL - 122

SP - 8797

EP - 8798

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 36

ER -

Discovery of the first metallaquinone [11]

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