Hydrogen-bonded networks from η5-semiquinone complexes of manganese tricarbonyl

Moonhyun Oh; Jeffrey A. Reingold; Gene B. Carpenter; Dwight A. Sweigart

doi:10.1016/j.jorganchem.2003.08.012

Hydrogen-bonded networks from η⁵-semiquinone complexes of manganese tricarbonyl

Moonhyun Oh, Jeffrey A. Reingold, Gene B. Carpenter, Dwight A. Sweigart

Department of Chemistry

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

10 Citations (Scopus)

Abstract

The cationic manganese tricarbonyl complexes containing η⁶ -2-methylhydroquinone (2a), η⁶-2,3-dimethylhydroquinone (3a), η⁶-2-t-butylhydroquinone (4a), η ⁶-tetramethylhydroquinone (5a) and η⁶-4, 4′-biphenol (6a) are readily deprotonated to the corresponding neutral (η⁵-semiquinone)Mn(CO)₃ (2b-6b) and anionic (η⁴-quinone)Mn(CO)₃^- (2c-5c) complexes. The X-ray structures of 2b-6b feature strong intermolecular hydrogen bonding interactions that result in the formation of supramolecular organometallic networks. Significantly, the substitution pattern at the semiquinone ring affects the stereochemistry of the hydrogen bonding interactions. NMR spectra of 2b, 3b and 5b reveal dynamic hydrogen bonding in solution.

Original language	English
Pages (from-to)	78-84
Number of pages	7
Journal	Journal of Organometallic Chemistry
Volume	687
Issue number	1
DOIs	https://doi.org/10.1016/j.jorganchem.2003.08.012
Publication status	Published - 2003 Dec 1

Bibliographical note

Funding Information:
Acknowledgment is made to the donors of The American Chemical Society Petroleum Research Fund for support of this research.

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

Access to Document

10.1016/j.jorganchem.2003.08.012

Cite this

@article{579d7544c19e44efbe512577a633580f,

title = "Hydrogen-bonded networks from η5-semiquinone complexes of manganese tricarbonyl",

abstract = "The cationic manganese tricarbonyl complexes containing η6 -2-methylhydroquinone (2a), η6-2,3-dimethylhydroquinone (3a), η6-2-t-butylhydroquinone (4a), η 6-tetramethylhydroquinone (5a) and η6-4, 4′-biphenol (6a) are readily deprotonated to the corresponding neutral (η5-semiquinone)Mn(CO)3 (2b-6b) and anionic (η4-quinone)Mn(CO)3- (2c-5c) complexes. The X-ray structures of 2b-6b feature strong intermolecular hydrogen bonding interactions that result in the formation of supramolecular organometallic networks. Significantly, the substitution pattern at the semiquinone ring affects the stereochemistry of the hydrogen bonding interactions. NMR spectra of 2b, 3b and 5b reveal dynamic hydrogen bonding in solution.",

author = "Moonhyun Oh and Reingold, {Jeffrey A.} and Carpenter, {Gene B.} and Sweigart, {Dwight A.}",

note = "Funding Information: Acknowledgment is made to the donors of The American Chemical Society Petroleum Research Fund for support of this research.",

year = "2003",

month = dec,

day = "1",

doi = "10.1016/j.jorganchem.2003.08.012",

language = "English",

volume = "687",

pages = "78--84",

journal = "Journal of Organometallic Chemistry",

issn = "0022-328X",

publisher = "Elsevier",

number = "1",

}

TY - JOUR

T1 - Hydrogen-bonded networks from η5-semiquinone complexes of manganese tricarbonyl

AU - Oh, Moonhyun

AU - Reingold, Jeffrey A.

AU - Carpenter, Gene B.

AU - Sweigart, Dwight A.

N1 - Funding Information: Acknowledgment is made to the donors of The American Chemical Society Petroleum Research Fund for support of this research.

PY - 2003/12/1

Y1 - 2003/12/1

N2 - The cationic manganese tricarbonyl complexes containing η6 -2-methylhydroquinone (2a), η6-2,3-dimethylhydroquinone (3a), η6-2-t-butylhydroquinone (4a), η 6-tetramethylhydroquinone (5a) and η6-4, 4′-biphenol (6a) are readily deprotonated to the corresponding neutral (η5-semiquinone)Mn(CO)3 (2b-6b) and anionic (η4-quinone)Mn(CO)3- (2c-5c) complexes. The X-ray structures of 2b-6b feature strong intermolecular hydrogen bonding interactions that result in the formation of supramolecular organometallic networks. Significantly, the substitution pattern at the semiquinone ring affects the stereochemistry of the hydrogen bonding interactions. NMR spectra of 2b, 3b and 5b reveal dynamic hydrogen bonding in solution.

AB - The cationic manganese tricarbonyl complexes containing η6 -2-methylhydroquinone (2a), η6-2,3-dimethylhydroquinone (3a), η6-2-t-butylhydroquinone (4a), η 6-tetramethylhydroquinone (5a) and η6-4, 4′-biphenol (6a) are readily deprotonated to the corresponding neutral (η5-semiquinone)Mn(CO)3 (2b-6b) and anionic (η4-quinone)Mn(CO)3- (2c-5c) complexes. The X-ray structures of 2b-6b feature strong intermolecular hydrogen bonding interactions that result in the formation of supramolecular organometallic networks. Significantly, the substitution pattern at the semiquinone ring affects the stereochemistry of the hydrogen bonding interactions. NMR spectra of 2b, 3b and 5b reveal dynamic hydrogen bonding in solution.

UR - http://www.scopus.com/inward/record.url?scp=0242287390&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0242287390&partnerID=8YFLogxK

U2 - 10.1016/j.jorganchem.2003.08.012

DO - 10.1016/j.jorganchem.2003.08.012

M3 - Article

AN - SCOPUS:0242287390

SN - 0022-328X

VL - 687

SP - 78

EP - 84

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

IS - 1

ER -