TY  - JOUR
A1  - Bock, Hans
A1  - Nick, Sabine
A1  - Näther, Christian
A1  - Bats, Jan W.
T1  - Strukturen ladungsgestörter Moleküle, 47 [1, 2]. Dinatrium- und Dikalium-Nitranilate: die Cyanin-Verzerrung der Kohlenstoff-Sechsringe
T1  - Structures of charge-perturbed molecules 47 [1, 2]. Disodium and dipotassium nitranilates: the cyanine distortion of the six-membered carbon ring
T2  - Zeitschrift für Naturforschung, B
N2  - Crystals of lemon yellow dipotassium nitranilate and of yellow disodium nitranilate di­hydrate have been grown and their structures determined at 290 and 200 K. The six-member- ed, O2N-disubstituted rings show a pronounced cyanine distortion with all four CO bonds identical and the two (OCC(NO2)CO)⊖ chains connected by single CC bonds of each 156 pm length. In the anhydrous K⊕ salt, the ring is planar, but in the Na⊕ hydrate salt it exhibits a twist conformation. Quantum chemical calculations allow to reproduce the structure in every detail, demonstrate strong charge alternation along the cyanine chains with considerable delocalization into the O2N acceptor substituents, and suggest that the rather long connecting CC bonds contain positively charged carbon centers on both ends. In addition, metal ion coordination effects as well as the rather high pKa value of nitranilic acid are rationalized.
KW  - Cyanine Distortion of C6-Rings
KW  - Single Crystal Structures
KW  - Semiempirical Calculations
Y1  - 2014
UR  - http://publikationen.ub.uni-frankfurt.de/frontdoor/index/index/docId/81646
UR  - https://nbn-resolving.org/urn:nbn:de:hebis:30:3-816462
SN  - 1865-7117
SN  - 0932-0776
VL  - 49.1994
IS  - 8
SP  - 1021
EP  - 1030
PB  - Verlag der Zeitschrift für Naturforschung
CY  - Tübingen
ER  -