%0 Journal Article %1 Frantz.2004b %A Frantz, Stephanie %A Rall, Jochen %A Hartenbach, Ingo %A Schleid, Thomas %A Zalis, Stanislav %A Kaim, Wolfgang. %D 2004 %J Chemistry - A European Journal %K DFT azophenine charge complex copper crystal prepn rhenium structure;mol structure;tautomer transfer %N 1 %P 149--154 %R 10.1002/chem.200305369 %T Metal-induced tautomerization of p- to o-quinone compounds: Experimental evidence from CuI and ReI complexes of azophenine and DFT studies %V 10 %X Azophenine (7,8-diphenyl-2,5-bis(phenylamino)-p-quinonediimine, Lp) reacts with Cu(PPh3)4(BF4) or Re(CO)5Cl to yield the (Ph3P)2Cu+ or (OC)3ClRe complex of the tautomeric form 7,8-diphenyl-4,5-bis(phenylamino)-o-quinonediimine, Lo, as evident from structure detns. and from very intense metal-to-ligand charge transfer (MLCT) transitions in the visible region. Time-dependent DFT (TD-DFT) calcns. on model complexes (N-N)Re(CO)3Cl (e.g., N-N = 1,4-dialkyl-1,4-diazabutadiene) confirm the spectroscopic results, showing considerably higher oscillator strengths of the MLCT transition for the o-quinonediimine complexes in comparison to compds. with N-N = 1,4-dialkyl-1,4-diazabutadiene. The complexes are addnl. stabilized through H bonding between two now ortho-positioned NHPh substituents and one fluoride of the BF-4 anion (Cu complex) or the chloride ligand (Re complex). DFT Calcns. on the model ligands p-quinonediimine or 2,5-diamino-p-quinonediimine and their ortho-quinonoid forms with and without Li+ or Cu+ are presented to discuss the relevance for metal-dependent quino-proteins. on SciFinder(R)

@article{Frantz.2004b, abstract = {Azophenine (7,8-diphenyl-2,5-bis(phenylamino)-p-quinonediimine, Lp) reacts with [Cu(PPh3)4](BF4) or [Re(CO)5Cl] to yield the (Ph3P)2Cu+ or [(OC)3ClRe] complex of the tautomeric form 7,8-diphenyl-4,5-bis(phenylamino)-o-quinonediimine, Lo, as evident from structure detns. and from very intense metal-to-ligand charge transfer (MLCT) transitions in the visible region. Time-dependent DFT (TD-DFT) calcns. on model complexes [(N-N)Re(CO)3Cl] (e.g., N-N = 1,4-dialkyl-1,4-diazabutadiene) confirm the spectroscopic results, showing considerably higher oscillator strengths of the MLCT transition for the o-quinonediimine complexes in comparison to compds. with N-N = 1,4-dialkyl-1,4-diazabutadiene. The complexes are addnl. stabilized through H bonding between two now ortho-positioned NHPh substituents and one fluoride of the BF-4 anion (Cu complex) or the chloride ligand (Re complex). DFT Calcns. on the model ligands p-quinonediimine or 2,5-diamino-p-quinonediimine and their ortho-quinonoid forms with and without Li+ or Cu+ are presented to discuss the relevance for metal-dependent quino-proteins. [on SciFinder(R)]}, added-at = {2019-07-15T13:41:23.000+0200}, author = {Frantz, Stephanie and Rall, Jochen and Hartenbach, Ingo and Schleid, Thomas and Zalis, Stanislav and Kaim, Wolfgang.}, biburl = {https://puma.ub.uni-stuttgart.de/bibtex/23859b14e0b32b9d4b336cfd4cfbf17a4/b_schwederski}, doi = {10.1002/chem.200305369}, interhash = {29347c1c4662607375eda0592e3c036e}, intrahash = {3859b14e0b32b9d4b336cfd4cfbf17a4}, issn = {0947-6539}, journal = {Chemistry - A European Journal}, keywords = {DFT azophenine charge complex copper crystal prepn rhenium structure;mol structure;tautomer transfer}, number = 1, pages = {149--154}, timestamp = {2019-07-15T11:42:10.000+0200}, title = {Metal-induced tautomerization of p- to o-quinone compounds: Experimental evidence from CuI and ReI complexes of azophenine and DFT studies}, volume = 10, year = 2004 }