Strukturen ladungsgestörter oder räumlich überfüllter Moleküle, 80 [1 - 3]. Strukturänderungen von p-Benzochinon durch Donator- und Akzeptor-Substituenten
Structures of charge-perturbed or sterically overcrowed molecules, 80 [1 - 3]. Structural changes of p-benzoquinone by donor and acceptor substituents
- The structures of seven di- or tetrasubstituted p-benzoquinone derivatives O=C(XC=CH )2C=O and O=C(XC=CX)2C=O with substituents X = -OCH3, -N(CH2)5, - N(CH2CH2)2O, -Cl, -CN and -⊕N(HC=CH)2C-N(CH3)2 are presented and discussed in comparison with published ones substituted by X = -Si(CH3)3, -C6H5, -N(CH3)2, -⊕N(HC=CH)2CN(CH3)2, -O⊖ , and - NO2. Based on the introduction, in which halfwave-reduction potentials, geometry-optimized quantum-chemical calculations on substituent perturbation and known structural data of p-benzoquinone derivatives are used to characterize their molecular ground states. The structural changes indicate how substituent perturbations might be rationalized. Of the categories defined - imperturbed, donor, donor/acceptor and acceptor perturbed - the donorsubstituted p-benzoquinones do exhibit the largest differences, often called cyanine distorsion. In very satisfactory agreement with extensive semiempirical calculations, all effects determined experimentally are discussed in terms of varying charge distribution. With respect to the biochemical importance of p-benzoquinone derivatives, this first structural summary points out important facets.
Author: | Hans BockGND, Sabine NickGND, Wolfgang SeitzGND, Christian NätherORCiDGND, Jan W. Bats |
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URN: | urn:nbn:de:hebis:30:3-816554 |
DOI: | https://doi.org/10.1515/znb-1996-0201 |
ISSN: | 1865-7117 |
ISSN: | 0932-0776 |
Parent Title (German): | Zeitschrift für Naturforschung, B |
Publisher: | Verlag der Zeitschrift für Naturforschung |
Place of publication: | Tübingen |
Document Type: | Article |
Language: | German |
Date of Publication (online): | 2014/06/02 |
Year of first Publication: | 1996 |
Publishing Institution: | Universitätsbibliothek Johann Christian Senckenberg |
Release Date: | 2024/01/19 |
Tag: | AM1 Calculations; Crystal Structure; Cyanine Distortion; Oxo-and Alkylamino-Substituted p-Benzoquinone Derivatives; Substituent Effects |
Volume: | 51.1996 |
Issue: | 2 |
Page Number: | 19 |
First Page: | 153 |
Last Page: | 171 |
Institutes: | Biochemie, Chemie und Pharmazie / Biochemie und Chemie |
Dewey Decimal Classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
Sammlungen: | Universitätspublikationen |
Licence (German): | Creative Commons - Namensnennung-Nicht kommerziell-Keine Bearbeitung 3.0 |