%0 Journal Article %1 Lichtblau.1993b %A Lichtblau, Alexander %A Hausen, Hans Dieter %A Schwarz, Wolfgang %A Kaim, Wolfgang. %D 1993 %J Inorganic Chemistry %K analog analog;crystal bipyridylidene boron boryl borylhydrobipyridylidene borylhydrobipyridylidene;electrochem borylhydrobipyridylidene;pyrazine borylhydropyrazine;mol hydro;Chichibabin hydro;Thiele hydrocarbon structure %N 1 %P 73--78 %R 10.1021/ic00053a012 %T Inorganic hybrid analogs of Thiele's and Chichibabin's hydrocarbons. Spectroscopy, electrochemistry, and structure %V 32 %X The formal substitution of external C:C bonds in quinonoid hydrocarbons such as 7,7,8,8-tetraaryl-p-quinodimethanes and 1,1'-biphenyl-4,4'-diylbis(diarylmethyl) compds. with the isoelectronic B:N function has occurred in 1,4-bis(dimesitylboryl)-1,4-dihydropyrazine (1) and 1,1'-bis(dimesitylboryl)-1,1',4,4'-tetrahydro-4,4'-bipyridylidene (2). These new inorg. hybrid analogs of Thiele's and Chichibabin's hydrocarbons are sufficiently electron-rich to allow chem. and electrochem. one-electron oxidn. despite the strong p acceptor effect of BMes2 substituents. Unusually small 11B and 14N EPR/ENDOR coupling consts. of the cation radicals 1.bul.+ and 2.bul.+ indicate a considerable degree of p bonding within the B:N units. The crystal structure of 2 as bis(benzene) solvate reveals a significantly higher degree of p electron bonding within the B:N units. The crystal structure of 2 as bis(benzene) solvate reveals a significantly higher degree of p electron localization than Chichibabin's hydrocarbon. The B-N distance of 144.4 (3) pm is close to that in borazine or hexagonal boron nitride. Huckel MO calcns. were used to interpret EPR/ENDOR, electrochem., and structural results. on SciFinder(R)

@article{Lichtblau.1993b, abstract = {The formal substitution of external C:C bonds in quinonoid hydrocarbons such as 7,7,8,8-tetraaryl-p-quinodimethanes and 1,1'-biphenyl-4,4'-diylbis(diarylmethyl) compds. with the isoelectronic B:N function has occurred in 1,4-bis(dimesitylboryl)-1,4-dihydropyrazine (1) and 1,1'-bis(dimesitylboryl)-1,1',4,4'-tetrahydro-4,4'-bipyridylidene (2). These new inorg. hybrid analogs of Thiele's and Chichibabin's hydrocarbons are sufficiently electron-rich to allow chem. and electrochem. one-electron oxidn. despite the strong \textgreek{p} acceptor effect of BMes2 substituents. Unusually small 11B and 14N EPR/ENDOR coupling consts. of the cation radicals 1.bul.+ and 2.bul.+ indicate a considerable degree of \textgreek{p} bonding within the B:N units. The crystal structure of 2 as bis(benzene) solvate reveals a significantly higher degree of \textgreek{p} electron bonding within the B:N units. The crystal structure of 2 as bis(benzene) solvate reveals a significantly higher degree of \textgreek{p} electron localization than Chichibabin's hydrocarbon. The B-N distance of 144.4 (3) pm is close to that in borazine or hexagonal boron nitride. Huckel MO calcns. were used to interpret EPR/ENDOR, electrochem., and structural results. [on SciFinder(R)]}, added-at = {2022-06-15T11:26:56.000+0200}, author = {Lichtblau, Alexander and Hausen, Hans Dieter and Schwarz, Wolfgang and Kaim, Wolfgang.}, biburl = {https://puma.ub.uni-stuttgart.de/bibtex/2df3efac867bb200f87ebc794b48d8787/huebleriac}, doi = {10.1021/ic00053a012}, interhash = {9ff7ff1372ae0fda97f9e1645f16f00f}, intrahash = {df3efac867bb200f87ebc794b48d8787}, issn = {0020-1669}, journal = {Inorganic Chemistry}, keywords = {analog analog;crystal bipyridylidene boron boryl borylhydrobipyridylidene borylhydrobipyridylidene;electrochem borylhydrobipyridylidene;pyrazine borylhydropyrazine;mol hydro;Chichibabin hydro;Thiele hydrocarbon structure}, number = 1, pages = {73--78}, timestamp = {2022-06-15T09:26:56.000+0200}, title = {Inorganic hybrid analogs of Thiele's and Chichibabin's hydrocarbons. Spectroscopy, electrochemistry, and structure}, volume = 32, year = 1993 }