TY  - JOUR
A1  - Bock, Hans
A1  - Nick, Sabine
A1  - Seitz, Wolfgang
A1  - Näther, Christian
A1  - Bats, Jan W.
T1  - Strukturen ladungsgestörter oder räumlich überfüllter Moleküle, 80 [1 - 3]. Strukturänderungen von p-Benzochinon durch Donator- und Akzeptor-Substituenten
T1  - Structures of charge-perturbed or sterically overcrowed molecules, 80 [1 - 3]. Structural changes of p-benzoquinone by donor and acceptor substituents
T2  - Zeitschrift für Naturforschung, B
N2  - 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.
KW  - Crystal Structure
KW  - Oxo-and Alkylamino-Substituted p-Benzoquinone Derivatives
KW  - Substituent Effects
KW  - Cyanine Distortion
KW  - AM1 Calculations
Y1  - 2014
UR  - http://publikationen.ub.uni-frankfurt.de/frontdoor/index/index/docId/81655
UR  - https://nbn-resolving.org/urn:nbn:de:hebis:30:3-816554
SN  - 1865-7117
SN  - 0932-0776
VL  - 51.1996
IS  - 2
SP  - 153
EP  - 171
PB  - Verlag der Zeitschrift für Naturforschung
CY  - Tübingen
ER  -