TY - JOUR
T1 - 1,4-Dialkyl-1,4-diazabutadienes
T2 - Their reactions with aluminum and indium halides
AU - Rojas-Sáenz, Héctor
AU - Suárez-Moreno, Galdina V.
AU - Ramos-García, Iris
AU - Duarte-Hernández, Angélica M.
AU - Mijangos, Edgar
AU - Peña-Hueso, Adrián
AU - Contreras, Rosalinda
AU - Flores-Parra, Angelina
PY - 2014/1
Y1 - 2014/1
N2 - Reactions of 1,4-bis[(S) methylbenzyl]-1,4-diazabutadiene (1), 1,4-bis[(R) 1′-chlorobutan-2′-yl]-1,4-diazabutadiene (2), 1,4-bis[(S,S) 1′-chloro-1′-phenyl-propan-2′-yl]-1,4-diazabutadiene (3), and 1,4-di-tert-butyl-1,4-diazabutadiene (4) with aluminum and indium halides were performed. Reaction of 1,4-diazabutadienes 1-4 with two equivalents of aluminum halides in toluene afforded ionic aluminum coordination compounds (5-10) which in THF solution are transformed into 1,3-dialkyl-2-methaneiminealkyl imidazolium heterocycles (11-14) by condensation of two 1,4-diazabutadienes and elimination of amine hydrochloride. Equimolar reactions of 1-4 with InCl3 in dry acetonitrile at -78 °C afforded the neutral and diamagnetic InCl 3 coordination compounds (15-18), which are stable in the solid state under dry conditions, but in THF solution are slowly transformed into the corresponding 1,3-dialkyl-imidazolium heterocycles 19-22. The X-ray diffraction analyses of compounds 2, 3, 10, 11, 14 and 17 are described. Quantum mechanical calculations were performed in order to find the minimum energy conformers of 1,4-diazabutadienes, 1,3-dialkyl-2-methaneiminealkyl imidazolium and 1,3-dialkyl-imidazolium derivatives as well as the aluminum and indium coordination compounds.
AB - Reactions of 1,4-bis[(S) methylbenzyl]-1,4-diazabutadiene (1), 1,4-bis[(R) 1′-chlorobutan-2′-yl]-1,4-diazabutadiene (2), 1,4-bis[(S,S) 1′-chloro-1′-phenyl-propan-2′-yl]-1,4-diazabutadiene (3), and 1,4-di-tert-butyl-1,4-diazabutadiene (4) with aluminum and indium halides were performed. Reaction of 1,4-diazabutadienes 1-4 with two equivalents of aluminum halides in toluene afforded ionic aluminum coordination compounds (5-10) which in THF solution are transformed into 1,3-dialkyl-2-methaneiminealkyl imidazolium heterocycles (11-14) by condensation of two 1,4-diazabutadienes and elimination of amine hydrochloride. Equimolar reactions of 1-4 with InCl3 in dry acetonitrile at -78 °C afforded the neutral and diamagnetic InCl 3 coordination compounds (15-18), which are stable in the solid state under dry conditions, but in THF solution are slowly transformed into the corresponding 1,3-dialkyl-imidazolium heterocycles 19-22. The X-ray diffraction analyses of compounds 2, 3, 10, 11, 14 and 17 are described. Quantum mechanical calculations were performed in order to find the minimum energy conformers of 1,4-diazabutadienes, 1,3-dialkyl-2-methaneiminealkyl imidazolium and 1,3-dialkyl-imidazolium derivatives as well as the aluminum and indium coordination compounds.
UR - http://www.scopus.com/inward/record.url?scp=84890261222&partnerID=8YFLogxK
U2 - 10.1039/c3nj01226c
DO - 10.1039/c3nj01226c
M3 - Artículo
SN - 1144-0546
VL - 38
SP - 391
EP - 405
JO - New Journal of Chemistry
JF - New Journal of Chemistry
IS - 1
ER -